Family friendly vacation rentals in Eastham, MA

14429 - Herring Brook Haven: 2025 Remodel! Walk to Pond, 2 Min Drive to Beach! If you thought a trip to this spacious retreat couldn’t get any better, over $300,000 of interior and exterior renovations were completed in 2025 and are ready to welcome guests! These include a brand new kitchen, the addition of 2 full bathrooms, renovation of the 2 existing bathrooms, brand new decking, interior and exterior painting, trim upgrades, and a revamped mini-split AC system. Escape to the quintessential Cape Cod retreat where every member of the family is invited to bask in the beauty of land and sea. Nestled within the tranquil embrace of Eastham, this expansive family home promises a week of relaxation and adventure, whether you’re lounging by the pristine shores of Herring Pond or exploring the scenic trails of the National Seashore.<br><br>Situated just a stone’s throw from the crystalline waters of Herring Pond, one of Cape Cod’s deepest and most pristine ponds, outdoor enthusiasts will delight in the array of recreational opportunities at their fingertips. <br><br>If you can pull yourself away from the comfort of the newly upgraded home, grab your bike and set off on an exhilarating journey along the rail-trail or meander through the quiet back roads, soaking in the natural splendor of the surrounding landscape.<br><br>Set upon a sprawling lot enveloped in privacy, this remarkable vacation home offers three levels of spacious living, ensuring ample room for everyone to spread out and unwind. Ascend to the top level (2nd floor), where a welcoming open-concept layout awaits, boasting a spacious kitchen (newly renovated), dining area, living space bathed in natural light, and half bathroom. Step out onto the expansive deck (newly re-constructed), where panoramic views of the enchanting natural landscape and glimpses of the famous First Encounter marshlands await. There is also a game room located above the garage and accessible via the exterior stairs/deck.<br><br>Back on the first floor, retreat to one of the three spacious bedrooms, each thoughtfully appointed to ensure a restful night’s sleep. Discover a queen bedroom with an en suite full bath room, a bedroom with two twin beds, and another room with a bunk bed (twin over full). There level also includes an additional full bathroom. Descend to the professionally finished basement, where a private laundry room awaits alongside two separate sleeping areas, furnished with a queen bed and a twin bed and a newly constructed bathroom. <br><br>From scenic vistas to ample space for gatherings, this fantastic vacation home offers the perfect blend of comfort, convenience, and coastal charm for an unforgettable Eastham getaway.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $45/night per dog)<br>-3 Floors: 1st Floor, 2nd Floor, Ground Floor<br>-Sleeps 8<br>Bedrooms<br>-Total: 4<br>-1st Floor Master Bedroom: 1 Queen Bed w/ en suite full bathroom<br>-1st Floor Bedroom: 2 Twin Beds<br>-1st Floor Bedroom: 1 Bunk bed (1 Twin Bed and 1 Full Bed)<br>-Ground Floor Bedroom: 1 Queen Bed and 1 Twin Bed (Semi-Private Sleep Area)<br>Bathrooms<br>-Total: 3.5<br>-1st Floor: Full Bathroom w/ Shower<br>-1st Floor: Full Bathroom w/ Shower (en suite Queen Bedroom) <br>-2nd Floor Half Bathroom<br>-Ground Floor: Full Bathroom w/ Shower/Tub combo<br>Other Amenities:<br>-Split A/C <br>-Cable TV<br>-WiFi<br>-Washer/Dryer in basement<br>-Tub<br>-Outdoor shower<br>-Private yard<br>-Gas grill<br>-Game Room<br>-Please note outdoor amenities are available seasonally <br>-There is parking for a maximum of 6 cars<br>-1-minute walking distance to the pond!<br>-Sheets and bath towels provided with beds made upon arrival<br>-Cleaned with hospital grade disinfectant<br>C0414890860

Exquisite in East Orleans, Heated Pool, Fire pit, Gym! Linens Included, Beds Made Pets Considered Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to The Breakaway, a stunning vacation home nestled in the picturesque Tonset Area of Orleans, Massachusetts. This luxurious property offers a perfect blend of comfort and elegance, making it an ideal retreat for families or groups seeking a memorable getaway. With 5 spacious bedrooms and 5.5 bathrooms, this home comfortably accommodates up to 14 guests, ensuring everyone has their own space to relax and unwind. As you step inside, you’ll be greeted by a beautifully designed interior featuring a gas fireplace that adds warmth and charm to the living area. The central air conditioning throughout the home ensures a cool and comfortable atmosphere, even on the warmest summer days. The fully equipped kitchen is a chef’s dream, complete with modern appliances, ample counter space, and a dining area perfect for family meals. The outdoor space is truly a highlight, boasting a heated private pool and a hot tub, perfect for soaking up the sun or enjoying a relaxing evening under the stars. The fenced yard provides a safe space for children and pets to play, while the outdoor seating areas and fire pit create an inviting atmosphere for gatherings. For those looking to stay active, the property features a gym and a game room equipped with a pool table and entertainment options, ensuring fun for all ages. Each bedroom is thoughtfully appointed, with the master suites offering TVs and sound systems for added convenience. Located just a short walk from the beach and near various attractions, including local Breweries and outdoor adventures, The Breakaway is the perfect base for exploring all that Cape Cod has to offer. Don’t miss out on this exceptional property—book your stay today and create unforgettable memories! Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14471 - Salt Water Sabbatical: Heated Saltwater Pool Hot Tub! In the woods of Eastham, a stunning oasis awaits. With your own heated in-ground saltwater swimming pool and hot tub, you’ll be soaking up the sun and salt water at the Salt Water Sabbatical. <br><br>The backyard is designed for long summer days and memorable evenings, featuring a private heated saltwater pool, hot tub, spacious stone patio, outdoor dining area, propane grill, fire pit, and outdoor shower. Whether you’re enjoying a morning swim, unwinding in the hot tub after the beach, or gathering around the fire pit under the stars, there’s no shortage of ways to enjoy your time outdoors.<br><br>When you’re ready to explore, you’ll be just minutes from both the Cape Cod Bay beaches and the Cape Cod National Seashore, making it easy to experience both the calm tidal flats and the Atlantic shoreline. Spend the day swimming, beachcombing, or watching the sunset before returning home to your own private oasis.<br><br>Inside, the bright, open layout is designed with comfort in mind. The first floor features a spacious living room with a Smart TV and home theater sound system, a beautifully appointed kitchen with a large center island, a half bath, laundry, and a queen primary suite with an en suite full bathroom. Upstairs, you’ll find three additional bedrooms—two with queen beds and one with two twin beds—along with two full bathrooms, providing plenty of space for everyone to spread out.<br><br>Whether your perfect vacation includes pool days, beach adventures, or simply enjoying the peaceful surroundings, Salt Water Sabbatical offers everything you need for an unforgettable Eastham escape. Book your stay today and experience the best of the Outer Cape.<br><br>Home Details:<br>-No Pets (Fines Remitted)<br>-Sleeps 8<br>-2 Floors (1st + 2nd Floor)<br>-2,400 Sq. Ft. <br>Bedrooms<br>-Total 4<br>-1st Floor: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor: 1 Queen Bed w/ Jack and Jill Full Bathroom<br>-2nd Floor: 2 Twin Beds w/ Jack and Jill Full Bathroom<br>Bathrooms<br>-Total 3.5<br>-1st Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo (Jack and Jill style)<br>-1st Floor: Half Bathroom<br>Other Amenities<br>-Central A/C<br>-WiFi<br>-Smart TV <br>-Washer and Dryer (1st Floor)<br>-Propane Grill<br>-Fire Pit<br>-Patio with Outdoor Dining and Lounging<br>-Outdoor Shower<br>-Private Heated Saltwater Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Hot Tub<br>-NO Pets (fines remitted) <br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0404030860

This property is Professionally Managed by Pretty Picky Properties. 5850 sq. ft. of Luxurious Summer Living, Heated Pool. 5 Minute Drive to Nauset Beach Sleeps 11 Rents Friday to Friday during peak season Linens Included, Beds Made Pool open from Memorial Day to Columbus Day The location is ideal: less than a 5-minute drive to world famous Nauset Beach and less than five minutes to Orleans Center with all its appealing shops, restaurants, galleries and Cape Cod League Baseball. Of course, now with a beautiful new heated saltwater pool in your back yard, you probably won’t go anywhere as often as you might otherwise! Around the pool is a generous pool patio that includes a huge umbrella-shaded loveseat, padded outdoor furniture, a gas fire-pit with Adirondack chairs and poolside loungers! This big, bright, magnificent contemporary home is located in the upscale Tonset neighborhood of Orleans. You will find plenty of room inside and out for your group of up to 12. Inside there is more than 5800 square feet of living space where your group can spread out and enjoy the perfect summer vacation. The expansive, private deck and spacious yard provides a great place to enjoy summer outdoor living, Cape Cod style. Here you’ll find the gas grill, umbrella shaded dining table, fire pit and enclosed outdoor shower. Inside, the thoughtful floor plan and tasteful décor elevate your vacation experience. There are five bedrooms in all; two master suites on the main level and three bedrooms upstairs. The first master bedroom has a king bed and walks out to the mahogany rear deck. There is a spacious, luxurious en suite bathroom featuring a jetted tub, separate step-in shower and a dual vanity sink. In addition, there is a sitting room off the master. The other master bedroom on the main level is outfitted with a queen bed and has a private full bath and access to the deck. The main level study also has a sleep sofa that converts to a full size double. Also on the main level you’ll find the generously sized chef’s kitchen, equipped with topline stainless steel appliances and amenities including, the Subzero® fridge, Viking® range and granite counters. The kitchen is light, bright and cheery, thanks to vaulted ceilings and plenty of windows. It opens to the dining and living areas so everyone can socialize during meal prep. The large flat screen TV is viewable from the kitchen as well. There is a breakfast counter with three seats for quick meals, kids’ snacks or kitchen kibitzers. Upstairs there are three bedrooms, one of which is outfitted with a Full bed and two Twin beds. It has its own private bath. Another bedroom on this level offers a queen bed and has a full private bath en suite. The final bedroom has two twin beds. There is also another pleasant lounge area on the upper level. The house has five full baths plus one half bath. The home is centrally air conditioned, has high speed Wi-Fi, smart TV with cable, and a Sonos® sound System. Recreational added value here comes in the form of a game room with a ping pong table in addition to kayaks provided for guest use. Once you experience this property and location, you’ll want to return for years to come, creating priceless memories of your family summer vacations on the Cape! Please enter your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 255.00 As is customary in vacation rentals there are additional fees to the rates listed. Those fees include $145 reservation fee and an $80 non-refundable Accidental Damage Protection (ADP) fee. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Please note: the pool is open Memorial Day - Columbus Day. This property offers a three-night minimum stay during select weeks in May – June and September – October. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is Professionally Managed by Pretty Picky Properties Luxurious Orleans Estate with Pool, Cabana, Game Room, and Stunning Finishes Sleeps 14 6 Bedrooms, 6.5 Baths Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pets Considered Pool is open from Memorial Day to Columbus Day Welcome to your dream vacation home in Orleans! This custom-built, newly constructed property offers the perfect blend of luxury and comfort, designed to make your Cape Cod getaway unforgettable. Main House Highlights 5 Spacious Bedrooms: Each bedroom features a private en-suite bathroom, ensuring comfort and privacy for all guests. There’s one king bedroom on the main level, the primary bedroom suite is upstairs with a king size bed, the other two rooms have a king and queen respectively. The lower-level bedroom is the kid lair with 2 sets of queen over queen bunks. Vaulted Ceilings: The open concept living, dining, and kitchen areas are bathed in natural light and exude sophistication with soaring ceilings and high-end finishes. Gourmet Kitchen: Fully equipped with top-of-the-line appliances, perfect for preparing meals and entertaining. Luxurious and custom décor throughout: no expense was spared in outfitting the home with décor and furniture rarely seen in a vacation rental property. Outdoor Oasis Heated Saltwater Gunite Pool: Take a refreshing dip or lounge poolside in style. Hot Tub: room for 6 to enjoy! Pool House with Cabana Bar: Enjoy cocktails by the pool with a full cabana bar, a bathroom, and an additional bedroom for added convenience and flexibility. Entertainment Galore Game Room: The massive game room is a paradise for kids and adults alike, featuring Pop-A-Shot basketball, ping pong, air hockey, and more. High-End Furnishings: Every room is thoughtfully decorated with custom, high-quality furnishings to elevate your stay. 5-minute drive to Orleans Center and Nauset Beach: shopping and dining or head to one of the best beaches on the Cape. Whether you’re lounging by the pool, hosting a family game night, or enjoying the luxurious finishes of this one-of-a-kind property, this Orleans retreat is the perfect base for your Cape Cod vacation. Book now and experience the pinnacle of coastal living! Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14447 - The Dive In: Beautiful Spacious Family Retreat w/ Pool! Look no further than this beautiful spot for your next Cape Cod getaway, the house is spacious, clean and has everything you need to enjoy a great vacation! The star feature is its huge fenced-in yard with gorgeous private pool, tall pine trees, and large deck for enjoying grilling out while the kids run around and play. You’ll also enjoy two separate living/relaxing spaces that each have their own TV, so two separate groups can enjoy watching whatever they like. The kitchen is modern and well equipped, which will make whipping up meals for a crowd a cinch. Your days can be spent relaxing at the beach, taking a Seal Tour in Chatham, Whale Watch in Provincetown, wine tasting at Truro Vineyards, and more —the mid and Outer Cape have so much to offer! Return home after a day of fun to take an outdoor shower, jump in the pool and unwind with friends and family under the stars from the comfort of your own backyard. Other amenities include WiFi, cable TV, gas grill, central A/C, and washer/dryer. Fresh sheets and bath towels are provided free of charge. <br> <br> Home Details:<br> -Sleeps 8<br><br>-2 Floors<br><br>-2nd Floor Bedroom #1: 1 King Bed<br><br>-2nd Floor Bedroom #2: 1 Full Bed<br><br>-2nd Floor Bedroom #3: 1 Full Bed<br><br>-2nd Floor Bedroom #4: 1 King Bed, 1 Twin Bed w/ Trundle<br><br>-2nd Floor Common Area: 2 Twin Beds<br><br>-Central AC <br><br>-Cable TV<br><br>-WiFi<br><br>-Washer/Dryer <br><br>-Private Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br><br>-Outdoor Shower<br><br>-Gas Grill<br><br>-NO DOGS! (heavy fines remitted)<br><br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br><br>-Cleaned with Hospital Grade Disinfectant<br>C0405890860

This property is professionally managed by Pretty Picky Properties. East Orleans Vacation Estate Includes Guest House, Heated Pool, hot tub Sleeps 12 6 Bedrooms, 6.5 Baths Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pets Considered - 25lb. limit Pool is open from Memorial Day to Columbus Day Privately ensconced on 1.25 acres in its charming East Orleans neighborhood, this exceptional property beckons your group of up to 12 for a Cape Cod vacation that will long be remembered fondly. The property is comprised of the main house plus a separate guest house, both the beneficiaries of the meticulous owners. Living Spaces: Naturally, the majority of the 4,190 sq. ft. of interior living space is found in the handsome main house. As you enter the welcoming foyer and proceed straight ahead, you’ll find yourself in the appealing dining area accommodating 12 around the table, with sliders out to the deck beyond. To your left, you’ll discover the gleaming and fully equipped chef’s kitchen with all high-end appliances, including a gas range and two dishwashers. The countertops are granite as is the generous center island with a prep sink and seating for 5. On the other side of the dining area, the beautiful and comfortable living room awaits, with its masterful furnishings and marble clad gas fireplace. There’s also a convenient half bath just off the kitchen. The home’s lower level provides a lounge with a complete wet bar, TV, and wine fridge. This space walks out to a good-sized patio with a firepit overlooking the pool. Kids of all ages will love the game room. Air Hockey, anyone? How about some arcade games? Out in the guest house, you’ll be impressed by the sense of space and light due to the two-story vaulted ceilings in the main living space. There’s also a full kitchen here with a center island with stool seating for three. There’s a handsome spiral staircase here that leads up to one of the guest house bedrooms. Sleeping Arrangements: This stunning home sleeps 12 in six bedrooms, each with its own private full bath ensuite. The main house has one of the property’s primary bedrooms on the main level. It has a big king-size bed, a good-sized TV and a walk-in closet. On the second level you’ll find another king primary bedroom and a second king bedroom that’s only slightly smaller. The lower level provides another bedroom and a private full bath. This one is a twin bed plus a pull-out second twin under. The property’s final two bedrooms are in the guest house. The main level bedroom has yet another king bed, also with a private bath; the second bedroom up the spiral staircase has a queen plus private bath. Outdoor Spaces: This vacation estate was created with outdoor summer living in mind. You can lounge on the large deck with an elevated view of the heated saltwater pool. The patio below may be where you decide to serve dinner most evenings. Why not? You have an umbrella shaded, ample dining table and chairs, and a big gas grill to fire up at any time. Walk down the steps from the deck to the stone patio and you’ll find the gas fueled fire pit and the enclosed outdoor shower. Maybe a quick dip in the pool and a few minutes in the soothing hot tub before dinner? This is truly Cape Cod outdoor summer living at its finest. Location: Not that you’ll feel the need to venture far from this resort-like property, it’s good to know your feet can be in the sweeping sands of world famous Nauset Beach in just an eight-minute drive. It’s just three minutes to East Orleans Village and Nauset Farms Market, known for their custom butcher shop, fresh local produce, generous deli sandwiches and mouthwatering homemade desserts. Or drive into Orleans Village Center to sample the unique shops, galleries and restaurants there, such as the addictive Hot Chocolate Sparrow. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This home is professionally managed by Pretty Picky Properties Grand Villa Overlooks Nauset Beach & the Atlantic, Heated Pool, Hot Tub & Gas Fire-pit! Rents Friday to Friday Off-season partial weeks available. Sleeps 14 Linens Included/Beds Made Pool and hot tub are open Memorial Day - Columbus Day Your group of up to 14 will vacation in style at this superb ocean side manor house at famous Nauset Beach in East Orleans. The stunning location provides panoramic views of the beach and ocean from both levels of the house. And you have a very short walk to the beach. The property also features a 36’x18’ heated pool, hot tub and gas fire pit!! The spacious, social, fully loaded kitchen anchors the main level and includes a breakfast bar with high boy seating for four. A few steps away, the large dining room easily seats 10 and can accommodate more. Relax in the exquisite living room with lounge seating and a large flat screen TV. This home has Sonos sound system off the back deck and in the lower level living space. It is centrally air conditioned and has hi-speed Wi-Fi and cable TV. A large, covered patio is just off the living room, with a dining table and chairs, plenty of lounge seating and views of the Atlantic. A separate lounge/bar room offers a wet bar with fridge, another TV, and bar seating for three. Walk out from there to a beautiful, hexagonal screened porch which leads to the pool deck. There is one bedroom on the main level, a roomy primary suite with a King size bed and full bath en suite with a walk in shower. The main level also includes a half bath and quiet den/study to serve as your work station, if necessary. On the upper level, you’ll first encounter another lounge area, which walks out to the upper deck that presents 180-degree breathtaking views of Nauset Beach and ocean. Comfy lounge seating here too, including a king-size super comfy sleeper sofa. On this level, you’ll find four more bedrooms. There’s a second, oversized primary suite, with a king size bed plus twin day bed with a twin trundle below. There is a full bath en suite, of course. Another bedroom suite features a King size bed and private full bath. Bedrooms #4 and #5 can be closed off to create a two-bedroom suite. Both bedrooms feature a queen size bed with a standard twin bed and twin trundle bed. The two bedrooms share a full bath between, Jack & Jill style. The lower level of the home houses an extraordinary full home theater with a projector, 10-foot screen and luxurious lounge seats with cup holders for up to 12, plus giant bean bag seating for more. What an amazing place should the weather not cooperate or for your evening entertainment. Also on this level: a workout room, a ping pong table, and a half bath. There are four full and two half baths in all. The yard and grounds provide plenty of space for kids to play safely. There is also a gas grill and horseshoe pits to keep everyone entertained. Consider planning your summer vacation at this truly remarkable property in one of Cape Cod’s most coveted locations. Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

15594 - Coast Away: Waterfront Oasis with Game Space, Newly Renovated! Let yourself be transported to effortless seaside living at Coast Away, a dog-friendly four-bedroom, two-bath waterfront oasis situated above Woods Cove in Orleans, complete with its own private beach just steps from the backyard. Here, 180-degree panoramic water views steal the show, especially from the expansive wrap-around deck where sunrise coffees and sunset laughter unfold to the soundtrack of the sea waves.<br><br>This coastal retreat comfortably accommodates up to eight guests, offering a plush queen bedroom on the first floor and, on the ground level, three additional queen bedrooms. With one full bathroom on each floor, convenience and comfort are built into your stay. The newly renovated and fully equipped kitchen, designed with the home chef in mind, invites you to prepare your favorite seafood dishes and gourmet creations. When the day winds down, gather for streaming movies on the Smart TV or head to the game space for some friendly competition around the foosball table—perfect entertainment no matter the weather. Central A/C and heat, washer and dryer, and an outdoor shower ensure every modern comfort of a perfect beach house escape.<br><br>A private path leads you down to your own stretch of beach, where you can dip your toes in the calm waves, launch your kayak, or rent a paddleboard and explore the peaceful cove. Sunbathe, read, or simply let the rhythm of the tide set the pace for your day. It’s easy to enjoy a nice meal cooked on the grill, eaten alfresco on the expansive deck at Coast Away, tailored to your every vacation need. The private yard offers plenty of space for kids and pets to play freely while you unwind by the fire pit. As night falls, sip your favorite drink beneath a starlit sky, feel the soft coastal breeze that Orleans is known for, and watch twilight settle gently over the water.<br><br>Beyond your retreat, you’re just a short drive from iconic beaches like Nauset Beach and Skaket Beach, celebrated for their spectacular sunrises and sunsets. On your way, stop at Nauset Farms for a fresh, delicious sandwich. Catch a summer game from the Cape Cod Baseball League at Eldredge Park. When it’s time to gather around the table, your favorite eateries await. Craving classic New England fare? The Barley Neck Inn has you covered. In the mood for Italian-inspired dishes? La Bella Vita Kitchen & Bar is the place to be. For live music and craft brews, Hog Island Beer Co. delivers the perfect evening vibe. Orleans downtown is just minutes away, offering charming boutiques and souvenir shops to complete your Cape Cod experience.<br><br>Let the waves, the breeze, and the view be your daily companions. Seize this rare waterfront gem, where every moment brings the ocean to your doorstep. Make your Cape Cod dream a reality at Coast Away.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 Queen Bed<br>-Ground Floor: 1 Queen Bed<br>-Ground Floor: Queen Bed<br>-Ground Floor: Queen Bed<br>Bathrooms<br>-Total 2<br>-1st Floor: Full Bathroom w/ Shower<br>Ground Floor: Full Bathroom w/ Shower/Tub Combo<br>Other Amenities<br>-Central via Split System<br>-WiFi<br>-Smart TV<br>-Streaming Service <br>-Washer/Dryer<br>-Indoor Fireplaces are not for guest use(fines remitted)<br>-Game Space<br>-Foosball Table<br>-Ping Pong Table<br>-Natural Gas Grill<br>-Gas Fire Pit<br>-Outdoor Shower <br> -Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 3 cars maximum<br>-C0572832240

This property is professionally managed by Pretty Picky Properties. "Second Wind" - An Orleans Estate with large heated pool, spa, on Town Cove Sleeps up to 24 in three dwellings Linens and bed making included Pets Considered up to 25 lbs. Weddings not permitted on property Pool is open Memorial Day - Columbus Day This Orleans Estate is located in the heart of Orleans Village on picturesque Town Cove. Bring the whole family and leave the cars in the driveway for the week. You’ll spend countless hours around the pool and spa at the Main House. There’s plenty of room for everyone to gather around the fire pit and cook out poolside at the outdoor kitchen. You can walk to everything in Orleans Center, including some of the best restaurants in town, village shops and of course, ice cream. There are four ice cream shops within walking distance! The mid-century homes have been recently updated with all the modern conveniences while retaining much of the original charm. The large 1.3 acre lot is waterfront on Town Cove and has a heated pool and spa (open Memorial Day - Columbus Day). The large lot provides plenty of recreation space on the gently sloping lawn. Hold your own version of the Whiffle Ball World Series. Town Cove is a great place to drop an owner-provided kayak or SUP and explore the in-land waterways of Nauset Cove and Nauset Marsh. Bring your boat and use the adjacent town boat ramp to motor your way to Nauset Beach by boat! The Main House underwent a full remodel in 2023, you have an updated kitchen with granite counters and new appliances, including a huge side-by-side refrigerator and two dishwashers. There are two dining areas along the back of the house so that large groups can dine together. There is also an enclosed porch overlooking the lawn, pool and cove beyond. The house is great for bringing family together but you have enough space to spread out as well. There are 3 large seating areas in the Main and Carriage Houses that are great spots to watch a ball game or for the kids to watch their shows/movies. The Main House has 5 bedrooms, 5 full baths and 1 half bath. You’ll find one of three primary suites on the main level of the Main House with a king size bed, sitting area and beautiful ensuite bath. There is also a powder room on the main level and living room with separate card-table room. Upstairs in the Main House, there are 3 bedrooms: the second primary suite with a king bed and a private full bath, the third primary suite features a king size bed and ensuite bath, and the third bedroom has a queen size bed with a twin bunk above. There is a full bath for guests of this room in the hallway with a tub/shower combination. In the lower level, you’ll find an extra sleeping area with 2 twin beds for overflow sleeping. Plus a wonderful new media room, laundry room and there is a full bath down here as well plus an outdoor shower not far away. Next door in the Carriage House, you’ll find a second full kitchen, a dining area, a powder room, a primary suite with king size bed and a private full bath on the main level. Upstairs in the Carriage House, you’ll encounter a loft space with a TV and cozy couch. There is a full bath and a bedroom with a queen sized bed plus 2 twins. The third structure, the Guest House has been fully remodeled – brand new kitchen with stainless steel appliances and granite counters. On the main level is a queen bedroom with full bath while upstairs you have a kid’s room with a bunk bed (full under a twin) and another twin with trundle bed with an en suite bath. The primary suite upstairs features a king size bed and stunning views of Town Cove with a wonderful en suite bath. The shower feels like an outdoor shower! In addition, the Guest House has an outdoor shower and 6-person hot tub overlooking the Cove. All three homes have AC, WIFI and cable TV. If you feel like leaving your own private resort, good news – two world famous beaches are less than 5 minutes’ drive away, Nauset Beach on the Atlantic or Skaket Beach on Cape Cod Bay. There is nothing that is overlooked at this ideal vacation property for larger groups. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a three night minimum stay during select weeks in May – June and September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

The Property is Professionally Managed by Pretty Picky Properties Close to Nauset Beach, Pool & Spa, Fire pit, Pool Table Sleeps 10 Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pets Considered Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to Perfect 10, a stunning newly constructed home located in the desirable Grand View Estates in East Orleans. This luxurious retreat offers a perfect blend of comfort and style, making it an ideal getaway for families or groups seeking relaxation and adventure. With 4 spacious bedrooms and 5 full bathrooms plus 2 half baths, this home comfortably accommodates up to 10 guests. Each bedroom is thoughtfully designed, featuring comfortable bedding and modern amenities, ensuring a restful night’s sleep. The main level boasts a King bedroom with a TV, while the second level includes a Queen bedroom, a kKing bedroom, and a Queen bedroom with a sleep sofa, all equipped with TVs for your entertainment. Step outside to discover your private oasis, complete with a heated pool and a hot tub, perfect for unwinding after a day at the beach. The outdoor space also features a gas fire pit, ideal for cozy evenings under the stars, and ample seating for gatherings. Inside, the home is equipped with central air conditioning, ensuring your comfort during warm summer days. The fully equipped kitchen is a chef’s dream, featuring modern appliances, a dining area, and all the essentials needed to prepare delicious meals. The living area is inviting and spacious, perfect for family gatherings or enjoying a movie night on the smart TV. For those looking to stay active, the property includes a game room with a pool table and ping pong table, as well as exercise equipment. Additionally, the home is pets considered, potentially allowing you to bring your furry friend along for the adventure. Located just a short walk from Nauset Beach, you can easily enjoy sun-soaked days by the ocean, as well as nearby attractions such as local shops, restaurants, and outdoor activities like hiking, fishing, and kayaking. Don’t miss the opportunity to experience this exceptional property. Book your stay at Perfect 10 today and create unforgettable memories in this beautiful coastal retreat! Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties Brand New Luxury Home in Orleans, Heated Pool, Steps to Town and Bike Trail Sleeps 10 in 4 bedrooms plus a bonus room Rents from Friday to Friday in Peak Season Linens included, beds made Pool is open Memorial Day to Columbus Day Welcome to “Liberty” a newly constructed home near downtown Orleans and convenient to Skaket and Nauset Beaches. This luxurious home features all new furnishings and décor, a heated saltwater pool and over 4,000 square feet of living area over three levels. The main level features soaring paneled ceilings in the main living area. The state-of-the-art kitchen is adjacent with a sizable island. The dining room is also in this area for easy prep and service of meals. There’s a cozy sunroom off the back of the main level as well for additional lounging and relaxation space. The primary bedroom is just off the kitchen and features a king-size bed, TV and a luxurious private bath. Upstairs, there are two bedrooms, one with a king-size bed and one with 2 full beds. There’s a shared bath up here with a shower/tub combo. The 4th bedroom is up a separate flight of stairs and has a king-size bed plus a private bathroom. The Lower level is expansive and has a movie room area, wet bar, full bath and easy access to the pool deck. There is also a king bed on the lower level for additional sleeping. The pool area has ample lounging area and of course a warm saltwater pool for use. Head out on foot or by bike and in moments you’ll be in downtown Orleans for dining, coffee, and shopping. The bike trail intersection is 0.4 miles from the house. Or maybe it’s a beach day! Skaket Beach on the bay is 1.5 miles or maybe the rolling waves of Nauset Beach is your fancy! Head 4 miles east for the open Atlantic. Vacation at Liberty! This luxury home has high-speed Wi-Fi, multiple smart TVs, and central air conditioning. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. ​​​​​​​ It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties. Private Orleans resort-style compound with heated pool & spa, fire pit and cabana Rents from Friday to Friday during summer weeks Linens included Pool & Hot Tub open from Memorial Day to Columbus Day Your multi-generational or multi-family summer vacation has found its home. Experience this stunning property with plenty of amenities for the entire family. The home features five bedrooms and sleeps up to 14 guests. The owners have added a heated salt water pool (18’x40’), hot tub and gas fire pit. There is also a cabana off the pool that features a sauna, full bar, half bath and comfy seating area with a big screen TV. In addition, there is a basketball hoop located off the back of the home. When you choose to venture out from your own private resort, world-famous Nauset Beach is less than a mile and a half down the road. Several restaurants, shops and an ice cream parlor are just a short walk away. Inside, on the main level, the open floor plan creates a wonderful space for the whole family to gather. You will find a chef inspired kitchen with high-end, stainless steel appliances including a gas range. The kitchen opens to a living area with large screen TV adjacent to a beautiful dining area. The main level provides two primary suites. Each is outfitted with a king size bed and en suite full bath. One of the primary suites has an enclosed deck with a commanding view of the magnificent patio and pool area. On the upper level, you’ll find three more bedrooms, each with a private bath. The first bedroom on the second floor features a queen size bed plus a day bed. Across the hall is another bedroom also with a queen size bed, a day bed plus en suite bath. The final bedroom upstairs is the perfect bunk room for the kids which is accessed from a separate stairway. It features two bunk beds (full size bed on the lower bunks) plus two twin beds, full bath and a private TV/game room. It’s a wonderful “clubhouse” where kids have their own space to play video games or watch their videos. This home is equipped with all the modern amenities you’d expect: high end furnishings, top quality bedding, central air conditioning, Wi-Fi, and cable TV. This property provides the accommodations you need for your group of up to 14 to enjoy your own private mini-resort. Whether it’s spending the day at the pool, relaxing in the sauna, or shooting hoops, the entire family can find something to enjoy. Once the day is done, marvel at the beautiful starry nights while dining al fresco on the deck. Or enjoy a beverage in the hot tub while discussing the plans for the next magical day on Cape Cod. Please note: pool and hot tub are open Memorial Day - Columbus Day. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Smell the sea air and listen to the soothing rhythm of the ocean at Sea Mist! A short 2/10ths of a mile from one of the most beautiful beaches on Cape Cod, this property brings together easy access to Nauset Beach with the luxury of a salt-water heated pool that includes a hot tub and sun shelf. Inside, the four bedroom house combines a quiet elegance with a cozy, beach house feel. On the first floor there is an airy ensuite queen bedroom with a double sink in the beautifully tiled primary bath. The large second bedroom has space for a private sitting area with a queen-size couch that converts to a second queen bed when extra sleeping space is needed. All the bedrooms include a desk where electronics can recharge or be put to use. Upstairs, a spacious king bedroom offers glimpses of the ocean and an alcove that holds a trundle bed with two twin mattresses. The room can easily accommodate a family of four or a kids sleepover! The fourth queen bedroom overlooks the pool and gardens and shares a stunning, remodeled bathroom with separate sinks and sea glass tile accents. On the main floor, the updated, fully-equipped kitchen includes a coffee bar (complete with a Keurig), ample work space, and high-quality appliances to make feeding your crew easy and enjoyable. Flip pancakes onto waiting plates at the gas-range island or gather around the large dining table in your banquet eat-in kitchen area. For special occasions tables can be arranged in the library for luxurious dining, with a gas fireplace bordered by built-ins adding to the charm. When not being used for dining, the library is a welcoming, cheery place for family game night, working on puzzles, and finding the perfect beach read. A second gas fireplace warms your evenings in the family room, where a 60-inch TV supports family movie nights or gaming sessions. In daylight, the high ceilings and generous transom windows make this room a perfect spot for sinking into a couch or chair with a good book and a nap on the horizon. If you prefer to dine and unwind outside, the sunroom and back deck are great options. Grill and crack lobster shells poolside on the deck, or steal away for some quite time in the serenity of the screened-in sunroom. The wooded conservation land next door provides added privacy to the beautifully landscaped grounds. The back yard is bounded on one side by a "secret garden" where children can play in outdoor bliss and everyone can find a quiet nook for reading and relaxing among the trees. The grassy lawn at the front can serve as a platform for badminton, corn hole or flashlight tag. Combining lovely spaces with fun features makes Sea Mist the perfect place for building life-long memories! All Linens are included. Large shed that locks is perfect for bike storage! Shed is stocked with a beach cart, pool toys, beach toys and beach towels!

This property is professionally managed by Pretty Picky Properties Luxurious 5- Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water! 5 bedrooms sleeps 12 Linens included, beds made Rents Friday to Friday in Peak Season Pets Considered (Small dog) Please note: pool and hot tub are open Memorial Day - Columbus Day. Escape to the heart of Lower Cape Cod in this newly renovated, luxury vacation home in East Orleans! Perfect for families and groups, this spacious 5-bedroom retreat offers the perfect blend of modern comfort and classic coastal charm. Inside, you’ll find a fully equipped, modern kitchen with everything you need to prepare gourmet meals, plus a large dining room with seating for 10 -- perfect for gathering after a day at the beach. The main level features two elegant bedrooms, both with a queens, each with new, spa-like private baths. Upstairs, two additional bedrooms. One has a spacious King and the other with a queen plus a twin with a trundle. There is a luxurious full bath upstairs as well. New for 2026: 5th bedroom as primary bedroom and private en-suite. Step outside and experience your private Cape Cod oasis -- a heated saltwater pool, relaxing hot tub, gas fire pit and a fully equipped outdoor kitchen make entertaining a breeze. Lounge in the poolside cabana, fire up the grill, or unwind under the stars after a day of exploring. Nature lovers will love the short walk to a nearby saltwater river, perfect for kayaking and paddleboarding. Plus, you’re just under a mile to Orleans Center for shopping and dining, and a 5-minute drive to both Nauset Beach and Skaket Beach—giving you the best of both the Atlantic Ocean and Cape Cod Bay. This stunning getaway has everything you need for an unforgettable Cape Cod vacation. Please enter in your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation, Get Picky! ®

This property is professionally managed by Pretty Picky Properties Brand New Luxury Home with Heated Pool, Walk to Rock Harbor Sleeps 10 Linens Included, Beds Made Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Ideally situated on the bay side of Orleans, this brand-new property features a 35’ x 18’ salt water heated pool, with a built-in spa and auto close cover. It is complemented by a large hardscape patio with plenty of lounge space. You can walk a mere 0.4 miles to scenic Rock Harbor for boat charters, seafood and the best sunsets on Cape Cod! There’s also a beach for swimming! Back at the house your group of up to 10 will be delighted with luxury living tastefully furnished throughout. Start with the custom chef’s kitchen, fully outfitted with top-line everything – from the high-end appliances to the 10-foot-long granite topped island with bar seating. The adjacent café dining table offers comfortable casual seating which walks out to the patio and pool. There is more formal dining for eight in the separate dining room as well. The kitchen flows into the adjoining sunroom which is bathed in cheery sunlight, thanks to the large windows, and vaulted, handsome bead-boarded ceiling with skylight. This level is also home to the primary bedroom suite with its generous king size bed and large private, radiant heat bath with a twin sink vanity and oversized step-in glass shower. Also located on the main level: a half bath, the laundry/pantry and mudroom. Upstairs are three generously sized en suite bedrooms: One has a king bed, the next has a queen bed. The final bedroom has a queen plus 2 twin beds. Comfy sleeping for up to 10. This luxury home has high-speed Wi-Fi, multiple smart TVs, and central air conditioning. Please enter in your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Please note: pool and hot tub are open Memorial Day - Columbus Day. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties. Upscale Vacation Estate with Heated Pool Near Nauset Beach Sleeps 12 Rents Friday to Friday in peak summer Linens Included, Beds Made Pool & Hot Tub open from Memorial Day to Columbus Day Completely renovated in 2024, here is the elite Cape Cod vacation experience your group of up to 12 is looking for. Start with location. World famous Nauset Beach is a mere 1.5 miles down the road. You can easily walk to the popular Barley Neck Inn and East Orleans Village with its inviting shops, ice cream and much more. Nauset Farms Market provides a professional butcher ready to assist you in choosing the ideal entree for that night’s grilling delight, as well as farm fresh produce, freshly made deli sandwiches and taste tempting homemade desserts. The property itself is a multi-structure compound, consisting of the main house, guest cottage, pool cabana, office/recreation center, and believe it or not, its own freestanding snack shack. Outdoor Living Space As you would expect, your outdoor living experience centers on the large, heated, saltwater pool and hot tub. You’ll find plenty of comfy lounge chairs for your poolside pleasure. The beautiful landscaping is a true delight. Be sure to experience the enclosed outdoor shower, a Cape Cod ritual that never gets old. Take a break from the sun in the poolside cabana. You’ll find a beverage center, half bath and laundry area inside. Put the gas grill to work and plan to dine on the large pool patio. You will also find a large firepit on the patio off the back of the main house. Indoor Living Space The fully equipped chef’s kitchen is a pleasure. New stainless-steel appliances and beautiful granite counters make meal prep a rewarding experience. The kitchen flows into the large dining area and family room with a gas fireplace. At the front of the house on the main level you’ll discover one of several recreation areas at this property, featuring a pool table. The guest house has a kitchen, living room and full bath. Still another structure at this property is the game room/office. It provides a work station, half bath and bar/lounge with a large TV. And then, just for fun, there’s the snack shack, which features a hot dog roaster, deep freezer for ice cream, refrigerator, and a sliding window for service. Sleeping Accommodations The main house has four bedrooms, each with a full bath ensuite. The upper level provides the king primary suite, and its beautiful private full bath is immense. It also has a gas fireplace and balcony overlooking the compound. There are two more bedroom suites upstairs via a separate stairway, one with a king size bed and the other with a queen. The lower level of the main house is home to three queen-sized beds and en suite bath. The guest house features a bedroom with a queen size bed and full private bath. In all the property has five full and three half baths. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This home is professionally managed by Pretty Picky Properties Luxury Brewster Estate – Pool, Hot Tub, Steps to Bike Trail "Brewster Barefoot Bliss" 3447-BMH Rents Saturday to Saturday in Peak Season Linens Included, Beds Made Six bedrooms, Seven Full Baths Sleeps Twelve Pets Considered **Additional separate two bedroom cottage available to rent next door, total occupancy of sixteen possible** Discover the perfect blend of classic Cape Cod charm and modern luxury at this stunning six bedroom vacation home in Brewster. With four private bedroom suites and space to sleep 12 guests, this expansive retreat is designed for relaxation and adventure alike for groups of any size. Location Nature lovers will appreciate the home’s prime location—adjacent to the popular Cape Cod Rail Trail bike path and just across the street from Nickerson State Park. Spend your days exploring the park’s scenic trails or take a short stroll (under a mile) to Crosby Landing Beach, considered Brewster’s best by many. You can be in downtown in Orleans in about two miles via the bike path. Outside Living Space No doubt most of your lounging and living will be done out on the spacious pool patio with a covered cabana area, gorgeous outdoor kitchen, a large dining table and chairs, a full bathroom and, of course, the heated pool. There’s also a hot tub and gas fire pit, ideal for gathering under the stars. You can whip up a feast in the cabana’s completely outfitted outdoor kitchen. The large, manicured yard is bordered by a tasteful variety of flowering plantings and makes a perfect place to throw a Frisbee ® or whack a Whiffleball ® And here’s an unusual extra amenity: your own private hockey rink! The special synthetic surface accommodates both roller blades and ice skates. Inside Living Space This home seamlessly blends classic coastal elegance with modern finishes, offering stylish and comfortable living spaces. The main level consists of a spacious and elegant kitchen, complete with everything you’ll need to prepare any meal and entertain any group. There’s seating for 12+ at the main dining table and adjacent round table plus there’s additional counter seating at the immense kitchen island. This part of the main level includes a wet bar, pantry and parlor. Fitness enthusiasts will appreciate the fully equipped gym. Then there’s the “Great Room,” which is nothing short of awe inspiring. Original to the structure, this room with soaring ceilings exudes old world charm in stunning fashion. The wood paneled walls are from a French chateau, the circular stairs from a British ship. Sleeping Accommodations The main level rounds out with two bedrooms, one with a queen, the other with a pair of twins, plus a full bath and a half bath. There are three, count ’em, three sets of stairs to the second level bedrooms. The first is off the small parlor and features a vintage narrow staircase to a queen bedroom with a private full bath. The second, more modern staircase leads to a second level area with two queen-bedroom suites, each with a private full bath. The final upstairs area is the most recent renovation and is essentially a self-contained apartment with a living area, kitchenette, king bedroom and a luxurious bathroom with a step-in shower, soaking tub and dual vanity. For a summary of bedrooms and bed configurations, use the Room Details tab above. Amenities This home has high speed WiFi, a Sonos® Sound System and central air conditioning. For a complete list of amenities, please click on the Amenities tab above. The owners reside in a smaller home on the grounds. so you can be sure that any issues that may arise will be quickly addressed. But you won’t see them unless you need them. Book now and experience the best of Brewster in this extraordinary vacation retreat. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for vacation rental on Cape Cod. It’s your vacation. Get Picky! ®

15595 - Dune Crest: Game Room, Central AC, Dog Friendly! Welcome to Dune Crest, a spacious Cape Cod getaway nestled in picture-perfect Orleans, MA—ideal for families and friends seeking comfort, relaxation, and coastal charm. <br><br>Unwind in this bright, airy, dog-friendly home featuring central air conditioning and plenty of space to spread out. The home offers four inviting bedrooms across two levels: three on the main floor—including a primary suite with a king bed and ensuite bath, plus two queen bedrooms—and a fun kids’ room on the lower level with four twin beds. With two additional full bathrooms, the home comfortably accommodates up to 10 guests.<br><br>The open-concept living and dining areas are designed for easy gathering, complete with WiFi and a fully equipped kitchen perfect for group meals. Start your mornings around the modern kitchen island with fresh coffee, or step outside to enjoy your peaceful yard. After a day of exploring, relax on the sunny patio, fire up the grill for a cookout, or share laughs around the wood-burning fire pit under the stars.<br><br>When it’s time to explore, you’re just minutes from some of Cape Cod’s best beaches. Skaket Beach—famous for its warm waters and spectacular sunsets—is less than a 10-minute drive away. Stop by Nauset Farms for fresh sandwiches and local treats before heading to the shore. A short drive brings you to Orleans’ charming Main Street, where you’ll find boutique shops and local favorites like Sunbird and Hole in One for breakfast, Land Ho! for casual lunch, or La Bella Vita for Italian-inspired dining. Don’t miss a scoop (or two) from Hot Chocolate Sparrow or Ice Cream Café on warm summer evenings.<br><br>For adventure, rent kayaks at Goose Hummock Shop, fish along Town Cove, bike the Cape Cod Rail Trail, or visit the Cape Cod Museum of Natural History—all just a quick trip from your home base.<br><br>Back at the house, keep the fun going in the dedicated game room, complete with a foosball table and Nintendo Switch. Wind down outside surrounded by classic Cape Cod natural beauty. Bring your group, your pup (pets welcome!), and settle into Dune Crest—where carefree beach days turn into cozy nights. Book your Orleans retreat today and start making memories at Dune Crest.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog) <br>-Sleeps 10<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 King Bed (Ensuite)<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-Ground Floor: 2 Day Beds w/trundle (4 Twin Beds Total)<br>Bathrooms<br>-Total 3<br>-1st Floor: Full Bathroom, with Shower (Ensuite w/ King Bed)<br>-1st Floor: Full Bathroom, with Tub/Shower Combo<br>-Ground Floor: Full Bathroom, with Shower<br>Other Amenities <br>-Central A/C (1st Floor)<br>-Mini Split AC (Ground Floor)<br>-WiFi<br>-Smart TV <br>-Game Room<br>-Foosball Table<br>-Streaming Service<br>-Washer/Dryer<br>-Propane Grill<br>-Wood Firepit <br>-Indoor Fireplaces are not for guest use (fines remitted)<br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 3 cars maximum<br>-C0442421152

This property is professionally managed by Pretty Picky Properties. Pochet Point Estate with Nauset Beach Access, Pool & Panoramic Views NEW Listing for 2026! Sleeps 16 Rents Friday to Friday during summer weeks Linens included Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to your East Orleans retreat—an extraordinary water-view estate in the coveted Pochet neighborhood, offering refined coastal living just steps from Nauset Beach. This Patrick Ahearn designed seven-bedroom, seven full and-two half-bath home spans three levels plus a pool house of luxurious living, thoughtfully designed for gathering, relaxation, and coastal adventure. The main level features a gourmet kitchen with high-end appliances, a spacious island, and seamless flow to multiple interior and exterior dining areas. Gather in the elegant great room or one of several inviting lounge spaces, each offering comfortable style and tranquil views of Pochet Inlet and the surrounding salt marsh. There are 5 bedroom suites each with a King bed and private bath. There is one bedroom on the main level and an additional four bedroom suites on the second level. The third floor offers two family-friendly rooms—one with two twin beds and another with two sets of twin-over-twin bunks—ideal for kids or groups. There is also a full bathroom on the third level as well. Step outside to your private resort setting: an oversized heated gunite saltwater pool, hot tub, and expansive pool deck designed for sun-soaked days and evening relaxation by the wood-burning fire pit. The magnificent Atlantic is your backdrop from the pool area. The ocean serenades you with the consistent calming wave action on the nearby shore. The pool house adds a layer of fun and function, complete with a game room, full bath, and laundry. From the backyard, a private neighborhood boardwalk leads you through protected dunes to world-famous Nauset Beach—a breathtaking walk to one of Cape Cod’s most iconic stretches of sand and surf. From the boardwalk you are accessing a secluded part of the beach to the south the public beach area. Plenty of space to set up camp and enjoy the rhythm of the Atlantic Ocean. Perfect for large families or multi-generational groups, this estate combines modern luxury, coastal charm, and unbeatable location—the ultimate East Orleans escape. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals, there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This home is professionally managed by Pretty Picky Properties Orleans: New Construction, Pool, Hot Tub, Close to What Counts Sleeps 10 Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pool open from Memorial Day to Columbus Day Welcome to Stillwater, a stunning luxury home nestled in the picturesque Arey’s Pond area of Orleans, Massachusetts. This newely constructed property offers an exquisite retreat for families and friends, accommodating up to 10 guests with its four spacious bedrooms and 4.5 bathrooms. Enjoy breathtaking views of the private heated pool and hot tub, perfect for relaxation and entertainment. Step inside this beautifully designed house, where modern elegance meets comfort. The main level features a luxurious primary bedroom with a king-sized bed, while the second level boasts two guest bedrooms, each with a queen-sized bed, and an additional primary bedroom with another king-sized bed. Each bedroom is thoughtfully appointed to ensure a restful night’s sleep. The heart of the home is the fully equipped kitchen, complete with a dishwasher, refrigerator, and an espresso maker, making it a chef’s dream. Gather around the dining area or enjoy meals al fresco in the outdoor eating area. The living space is designed for relaxation, featuring a cozy private living room and a game room with a pool table and ping pong table for endless fun. Step outside to your private oasis, where you can soak in the heated pool or unwind in the hot tub. The outdoor space also includes a gas grill and fire pit, perfect for evening gatherings under the stars. Safety features such as smoke detectors, fire extinguisher, and a carbon monoxide detector ensure peace of mind during your stay. For those looking to explore, the property is conveniently located near beautiful beaches, golf courses, and local attractions such as Nauset, Beach, Skaket Beach, and a small freshwaster beach on Crystal Lake. Whether you’re seeking adventure or relaxation, Stillwater is the perfect destination. Don’t miss out on this luxurious getaway—book your stay at Stillwater today and create unforgettable memories! This home has high speed Wi-Fi, smart TV’s, a SONOS sound system and central air air conditioning. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Private, Spacious, Pristine with Heated Pool 7-Night minimum for June, July & August Linens Included, Beds Made Rents Friday to Friday in Peak Summer Pool open from Memorial Day to Columbus Day Welcome to Orleans Oasis, a stunning vacation home nestled in the picturesque neighborhood of Pleasant Bay in South Orleans. This spacious house offers a perfect blend of luxury and comfort, making it an ideal retreat for families or groups seeking a memorable getaway. With a generous 3,450 square feet of living space, this property comfortably accommodates up to 10 guests across its four beautifully appointed bedrooms and three bathrooms. As you step inside, you’ll be greeted by an inviting ambiance that features updated interiors and modern amenities. The main level boasts a master bedroom with a king-sized bed, while the second floor offers three additional bedrooms, including another king suite, a room with a double bed and twin singles, and a cozy queen bedroom. Each room is designed for relaxation and comfort, ensuring a restful night’s sleep. The heart of the home is the expansive living area, perfect for gathering with loved ones. Enjoy the convenience of a fully equipped kitchen, complete with a kitchen island, dining table, and modern appliances, including a dishwasher and microwave. The living room is ideal for unwinding, featuring comfortable seating and entertainment options such as a television and games. The lower level unfinished space is home to the ping pong table. Step outside to discover your private oasis. The outdoor space features a heated pool, perfect for a refreshing dip, and a wood fire pit for cozy evenings under the stars. The patio provide ample space for outdoor dining and relaxation, making it easy to soak up the sun or enjoy al fresco meals. For those seeking adventure, the property is conveniently located near a variety of attractions, including beautiful beaches, golf courses, and opportunities for fishing, hiking, and whale watching. Whether you’re looking to explore the local area or simply relax by the pool, Orleans Oasis is the perfect home base for your Cape Cod vacation. Don’t miss out on the chance to experience this exceptional property. Book your stay at Orleans Oasis today and create unforgettable memories with family and friends! Please enter your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Families Welcome | Multiple Living Spaces | 2 Mi to Nauset Beach Embark on your dream East Coast getaway and stay at this charming 5-bedroom, 3.5-bathroom Orleans vacation rental! Nestled near pristine beaches, lush golf courses, and other fun-filled activities, this abode offers an idyllic home base while you explore the Cape Cod area. Spend your days splashing in the saltwater, then head into town and indulge in an iconic lobster roll for dinner. Adventure awaits; book your trip today! -- THE PROPERTY -- C0521792240 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 king bed - Bedroom 3: 1 queen bed - Bedroom 4: 2 twin beds - Bedroom 5: 1 twin bed - Additional Sleeping: 1 portable crib (bring your own sheets) MAIN FEATURES - Smart TVs, books/board games - Dining tables - Fireplace (decorative only) - Furnished sunroom, multiple living areas - Spacious yard - Grill KITCHEN - Refrigerator, microwave, stove/oven, dishwasher - Keurig & drip coffee makers, toaster - Cooking basics, dishware/flatware GENERAL - Free WiFi - Central heating, window A/C unit, ceiling fans - Washer/dryer - Towels & linens, trash bags & paper towels ACCESSIBILITY - 2-story home, 2 steps required to enter - 1st-floor bedroom & full bath PARKING - Garage (2 vehicles) - Driveway (4 vehicles) -- THE LOCATION -- - Close to Downtown Orleans - 2-11 miles to Nauset Beach, Skaket Beach, Coast Guard Beach & Lighthouse Beach - 2 miles to Cape Cod Rail Trail & 4 miles to Fort Hill Trail - 6 miles to Cape Cod National Seashore Salt Pond Visitor Center - 6-12 miles to The Captains Golf Course, Chatham Seaside Links & Cranberry Valley Golf Course - 9 miles to Cape Cod Museum Of Natural History & 14 miles to Cape Cod Museum of Art - 22 miles to Cape Cod Gateway Airport & 92 miles to Boston Logan International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires 2 steps to enter; it features a bedroom and full bathroom on the 1st floor - The fireplace is decorative only - Sheets are not provided for the Pack 'n Play; it is recommended that you supply your own Licence number: RC-2025-221;C0521792240;RENT-276

This property is professionally managed by Pretty Picky Properties. Orleans Oasis on Pleasant Bay, 2 Homes and Heated Pool; "Beam Reach" Sleep up to 14 Rents Friday to Friday in Peak Season Linens Included, Beds Made Pets Under 25 Pounds Considered Pool is open from Memorial Day to Columbus Day weekend Welcome to your private oasis on Pleasant Bay. At the end of the road you will find this private setting which features 2 homes located right on the water. Windward and Leeward are two wonderful homes that will provide you and your family of up to 14 with great Cape Cod memories. There is a beach area just outside the back door of the Windward home. And there is a heated pool between the two houses for those who prefer a pool to the Bay. Windward was completely remodeled recently. All new furnishings and a brand new kitchen. Sit in the living room and enjoy tremendous views of Pleasant Bay. There are a total of 3 bedrooms in Windward. The first features a queen size bed with an ensuite bath. The views are amazing from here! The second bedroom has a comfy king size bed along with an ensuite bath. The third bedroom is located through the walk-in closet and offers a twin-over-full bunk bed. There is a private entrance to this room off of the front porch. These two bedrooms are set up perfectly for a family with kids. There is also a half bath, brand new kitchen and laundry. And of course the home is outfitted with central AC and Wi-Fi. Leeward is on the other side of the pool and features 3 more bedrooms. On the main level you will find a cozy living room, full kitchen and a large screened in porch. There is also a dining room, full bath and two bedrooms on this level. The first bedroom features two twin beds. The other bedroom has a queen size bed and an ensuite bath. Upstairs you’ll find a suite perfect for a family with kids. There is a king size bed plus two twin beds up there in addition to a full bath. The Leeward home also features a wonderful media room in the lower level. A brand new 75” TV is ready for movie night! There is a cozy sectional sofa, a kitchenette, small refrigerator and a popcorn machine making this the best spot for movie night or in case the weather doesn’t cooperate. There is also a full bath, exercise equipment and laundry facilities down stairs. And while the homes are beautiful on the inside you will undoubtedly spend most of your time enjoying the outdoors. The pool (12’x24’), which has a fence around the outside for safety, is heated so it’s a great option even in June or September (pool is heated from Memorial Day – Columbus Day). There is a large table inside the pool area for dining al fresco! And the views from the pool area are awesome. There is an outdoor fire-table for enjoying the evenings under the stars listening to the water against the shoreline. And of course no Cape vacation home is complete without an outdoor shower! In addition, the owners provide kayaks and stand-up-paddle boards. This property offers a wonderful Cape escape. You will feel like you’ve gone back to a simpler time but thanks to all the modern amenities you’ll still enjoy today’s creature comforts. A SONOS system, central AC, heated pool, flat screen TV’s and Wi-Fi throughout will allow you to enjoy your vacation in comfort. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®