Large group vacation rentals in Orleans, MA

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 $ 245.00. 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! ®

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 $ 245.00 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! ®

15531 - Maplewood Manor: Walk to Town, Fully Renovated! Discover the charm of Orleans in this thoughtfully renovated vacation home, blending historic character with modern luxury. Located just 2.4 miles from Skaket Beach and 2.6 miles from Nauset Beach, this spacious retreat is the perfect haven for families and friends. Stroll 0.3 miles to Main Street for dining, shopping, and bike rentals, or explore the nearby Town Cove for boating and kayaking adventures.<br><br>Inside, the home comfortably sleeps 12, accommodating up to 12 guests across six bedrooms and a lofted space. The first-floor bedroom offers a king bed, while the second floor features three more bedrooms, including a king bed bedroom, a full bed bedroom and two twin-bed options. The third-floor is a great suite for kids, with a murphy bed that sleeps two, a futon, and 2 bedrooms, one with a full and one with a twin bed.<br><br>Relax in the fully fenced yard, perfect for kids to roam while you grill on the gas BBQ or gather around the fire pit under the stars. Indoors, enjoy a Viking stove for culinary creations, central AC for ultimate comfort, and a soaking tub for unwinding after sun-soaked beach days. Walk to La Bella Vita for Italian fare or The Corner Store for their famous burritos, and end your evening with a nightcap on the lantern-lit front porch.<br><br>Your perfect Orleans getaway is waiting. Book today and make memories that last a lifetime!<br><br>Home Details:<br>-No Pets(Fines Remitted)<br>-Sleeps 12<br>Bedrooms<br>-Total 6<br>-1st Floor Bedroom: 1 King Bed w/ Ensuite bathroom<br>-2nd Floor Bedroom: 1 Full Bed w/ Ensuite bathroom<br>-2nd Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 2 Twin Beds<br>-3rd Floor Bedroom: 1 Full Bed<br>-3rd Floor Bedroom: 1 Twin Bed<br>-3rd Floor Lofted Space: 1 Full Murphy Bed<br>Bathrooms<br>-Total 3.5<br>Other Amenities <br>-Central AC<br>-WiFi<br>-Cable TV<br>-Washer/Dryer <br>-Gas Grill<br>-Fire pit<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 4 cars maximum<br>-C0196972240<br>

The perfect location! Ten minute walk to Cape Cod Baseball...fifteen minute walk to Orleans center...five minute walk to bowling...extraordinary playground next door with fields and tennis courts...five minutes by car to the Bay beach, ten minutes to Nauset. This versatile home has five bedrooms and two and a half baths. The kitchen is modern, with a Viking range and granite counters including a large island, and open to a full dining room with sliders to the deck with a Weber grill. The five bedrooms will sleep as many as 10 people. The sitting area downstairs includes a 52 in Smart TV and a washer and dryer. There is also a second kitchen for snacks! The living room has an electric recliner and a 65 in Smart TV. Right outside the back door is a spacious outdoor shower. Plenty of parking for you and your guests. You won’t find a more family friendly house! Lots of fun outdoors with provided tennis racquets, baseball/softball equipment, corn hole game, wiffleball and plastic racquet game with balls. One bicycle available to use too! Ac unit recently added to the lower level too! **Blankets and Pillows are provided, but you will need to bring or rent sheets and towels**

Located right on the shore of beautiful Town Cove in Orleans. This updated home has 3 bedrooms 2 1/2 baths Nicely appointed foyer and living room with expansive saltwater views, leads you to the sunroom, deck and pathway to the water (conservation protected, can get overgrown depending on the time of year.) Games and books fill bookcases and a large flat screen TV sits ready to fill a rainy day if needed. The kitchen is clean and bright and has a dining area overlooking the water. Unwind in the enclosed porch or out on the deck as the sun sets over town center. There are 2 bedrooms on the first floor, each with 2 twins. The one facing the Cove even has it’s own en-suite half bath. There is also a full bathroom with a shower on the first floor. Upstairs is a newly renovated primary suite with a king bed and private full bath. Views of the water abound from the large picture window. Outdoor shower for rinsing off after the beach. Gas grill for outdoor cooking. Central a/c to keep you cool. Washer and dryer is accessed from outdoor space off the kitchen. This property is perfect for the water sports lover in the family. Fish, clam, kayak, sail and more. MA Registration: C0039432240

15504 - Harbor Haven: 1 min drive to Rock Harbor, 2 min to Town! Nestled just a stone’s throw from the pristine shores of Rock Harbor and the family-friendly haven of Skaket Beach in Orleans, this newly renovated cottage epitomizes seaside charm and relaxation. Whether you’re seeking a romantic retreat or a beachside getaway for a family of four, this picture-perfect abode offers the perfect blend of comfort and convenience for your vacation.<br><br>Step inside to discover a haven of tranquility, where a spacious master bedroom beckons with its understated elegance, while vaulted ceilings adorn the cozy bunk room, creating a whimsical retreat for the little ones. Gather in the sunlit eat-in kitchen, complete with new appliances and ample space for culinary creations.<br><br>Relax and unwind in the comfortable living room, basking in the warmth of natural light streaming through the windows, or retreat to the newly added screened-in front porch, where gentle breezes create an idyllic setting for leisurely afternoons.<br><br>Entertainment abounds with a large flat-screen TV offering Netflix and other on-demand options, ensuring endless evenings of relaxation. Central AC provides respite from the summer heat, while an outdoor gas grill invites alfresco dining beneath the stars.<br><br>Outside, the lush yard invites exploration, with space for children to play and a charming one-room dollhouse cottage. Pack your beach toys, golf clubs, and tennis rackets, as this centrally located cottage offers easy access to the area’s renowned restaurants, boutiques, and recreational activities, ensuring a memorable Cape Cod experience for all.<br><br>Home Details:<br>-No dogs (fines remitted)<br>-Sleeps 5<br>-1 Floor<br>-Bedroom<br>-Total: 2<br>-1st Floor Master Bedroom: 1 King Bed<br>-1st Floor Bedroom: 1 Twin Bunk Bed and 1 Twin Trundle Bed (3 Twins total)<br>Bathrooms<br>-Total: 1<br>-1st Floor: Full bathroom w/ Shower<br>Other Amenities<br>-Central AC<br>-Private Yard<br>-Outdoor shower<br>-TV <br>-Washer/Dryer in basement<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Please note outdoor amenities are available seasonally<br>-There is parking for a maximum of 4 cars<br>-Cleaned with Hospital Grade Disinfectant<br>C0419542240

15566 - Firebird Fanfare: Fantastic Home by Eldridge Park! Orleans, home to world famous Nauset Beach and a renowned Cape Cod Baseball League team, welcomes you to your next stay with some Firebird Fanfare! Push open the lobster-red front door and enter into the home’s living room, with wall mounted TV adjacent to the open concept dining room and large dining table. The home’s eat-in kitchen has plenty of counter space and natural light flooding in through the bay window, seemingly bringing the beauty of the Cape indoors. <br><br>If you want to dine and feel the salty breeze, head out to the screened in porch and eat underneath the vaulted ceilings and exposed wood beams. This additional room is a great place to cool off after enjoying the summer sun! Back inside, a bedroom with two twin beds and views of the greenery out front is a great place for the kids to count sheep. Upstairs, the remaining bedrooms can be found, each with a queen bed and additional seating areas, the perfect spots to reading your favorite book before bed.<br><br>Other amenities include a washer and dryer, central A/C, and an outdoor shower. Just down the road, cut through the wooded trail to an incredible playground at the local school, sure to be a highlight for your kids this vacation. Hear the crack of the bat and roar of the crowd this summer, with some Firebird Fanfare!<br><br>Home Details:<br>-Sleeps 6<br>-2 Floors (1st + 2nd Floor)<br>-1,483 Sq. Ft.<br>-3 Bedrooms<br>-Bedroom #1: 2 Twin Beds, 1st Floor<br>-Bedroom #2: 1 Queen Bed, 2nd Floor<br>-Bedroom #3: 1 Queen Bed, 2nd Floor<br>-2 Bathrooms<br>-Bathroom #1: Full Bathroom with Shower, 1st Floor<br>-Bathroom #2: Full Bathroom with Tub/Shower Combo, 2nd Floor<br>-Fully Equipped Kitchen with Dishwasher<br>-Central A/C<br>-Fireplace is NOT for guest use<br>-WiFi<br>-Smart TV with Streaming<br>-Washer and Dryer (1st Floor)<br>-Propane Grill<br>-Deck with Outdoor Dining<br>-Large Screened-In Porch<br>-Outdoor Shower<br>-NO PETS (fines remitted)<br>-2 Minute Drive to Eldridge Park, Orleans Firebirds Ballpark<br>-6 Minute Drive to Skaket Beach<br>-Conveniently located next to a School with Playground, Basketball Court and Fields<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0407252240

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 $ 245.00 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! ®

Immaculate and beautifully renovated three bedroom home just 1/2 mile to both Orleans Main Street and Rock Harbor. This sunny and bright home is set back from the road and offers privacy and the charm of Cape Cod. Main level with living room w/TV, dining room, fully equipped kitchen, two bedrooms (both with TVs) and one full bath. Upper level offers a spacious open room with twin beds and a hangout space with seating and large flat screen TV. Enjoy a day at the Rock Harbor Beach and the spectacular sunsets or head to Skaket Beach which is just 1 mile away. Central AC, Outdoor Shower, cooler, beach chairs, and beach toys. New patio! **Blankets and Pillows are provided, but you will need to bring or rent sheets and towels**

15518 - Time Out: Beach Getaway with Private Backyard! At this serene Orleans retreat, where salt air and sunshine beckon just minutes from the pristine shores of Skaket Beach, it’s time to take a well-deserved Time Out and embrace the leisurely pace of coastal life. A sunset-orange facade welcomes you to this inviting Cape house, where the first floor unfolds to reveal a spacious, brand new kitchen for effortless meal preparation and a delightful dining area beckoning with promises of shared meals and cherished moments. Gather in the cozy living room for movie nights or indulge in family games around the dining table, fostering bonds and creating memories that will last a lifetime. Step outside to discover the exceptional outdoor space, where a private backyard offers ample room for your furry friend to frolic as you fire up the grill for al fresco dining. Lounge on the sprawling deck, surrounded by lush greenery and endless possibilities for relaxation and rejuvenation. Retreat indoors to discover a serene primary suite on the first floor, offering a tranquil haven for rest and relaxation after a day of exploration. Upstairs, three additional bedrooms await, including one with two full-size beds ideal for the kids, another with twin beds, and a semi-private lofted bedroom boasting a queen-size bed, ensuring ample space for the whole family to unwind in comfort. Additional amenities include a washer and dryer for added convenience, as well as an outdoor shower offering a refreshing respite after sun-drenched beach days. With a plethora of dining and entertainment options just moments away, your vacation promises endless opportunities for adventure and relaxation. It’s time to embark on a fantastic getaway – it’s time to take some Time Out and create cherished memories amidst the beauty of Cape Cod. Home Details: -Dogs Welcomed (w/fee of $40/night per dog) -Sleeps 10 -2 Floors (1st Floor + 2nd Floor) Bedrooms -Total 4 -1st Floor: 1 King Bed with En Suite Full Bathroom -2nd Floor: 1 Queen Bed -2nd Floor: 2 Full Beds -2nd Floor: 2 Twin Beds Bathrooms -Total 3 -1st Floor: Full Bathroom w/ Shower (ensuite King Bedroom) -1st Floor: Full Bathroom w/ Shower -2nd Floor: Full Bathroom with Shower Other Amenities -fireplace is not for guest use -Window A/Cs in Bedrooms -TV -WiFi -Washer and Dryer (1st Floor) -Outdoor Shower -Private Yard -Deck with Outdoor Dining -Propane Grill -Minutes from Skaket Beach -please note outdoor amenities are available seasonally -There is parking available for a maximum of 3 cars -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant C0413102240

15564 - Rock Harbor Rendezvous: Less than .5 Miles to Rock Harbor! Hear the seagulls calling in the distance as you breathe in the fresh salty air - your calming Cape Cod vacation awaits, at the Rock Harbor Rendezvous. <br><br>Step inside and you’ll be welcomed by a beautiful kitchen featuring a modern backsplash, a center island with a breakfast bar, and natural light pouring in from the skylight above. Just beyond the kitchen is the home’s open-concept dining and living area. With plenty of seating in the living room, it’s the perfect place to unwind and enjoy a movie or two during your vacation. The dining room table sits beneath a charming chandelier, while patio doors allow sunlight to stream in throughout the day.<br><br>Down the hall from the living room, you’ll find two of the home’s four bedrooms. The first bedroom features a twin bed with a pull-out trundle, along with a cozy seating area and desk. The second first floor bedroom offers a queen-size bed with pleasant views of the front and side yards. Upstairs are the remaining bedrooms. To the left of the stairs is the primary bedroom, complete with a spacious king-size bed and an additional seating area with a desk. The final bedroom includes one twin bed and one full-size bed, offering plenty of space for kids to spread out and recharge before another day of Cape Cod fun.<br><br>Outside, the home’s amenities continue. The back deck stays cool beneath a shade sail, making it a great spot for outdoor dining. Step down to the patio, where you’ll find a gas fire pit and comfortable lounge seating—perfect for relaxing in the evening. Less than half a mile up the road, enjoy the bay and take in a stunning sunset at Rock Harbor. You can also head into downtown Orleans and visit the Hot Chocolate Sparrow for some delicious treats.<br><br>Whether you’re looking to relax at home all vacation long or want the perfect home base for exploring Cape Cod, you won’t find a better place than Rock Harbor Rendezvous.<br><br>Home Details:<br>-No Pets (Fines Remitted)<br>-Sleeps 9<br>-2 Floors<br>-1,995 sq. ft.<br>Bedrooms<br>-Total 4 <br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Twin Bed w/ Twin Trundle (2 Twins total)<br>-2nd Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 1 Full Bed and 1 Twin Bed<br>Bathrooms<br>-Total 2<br>-1st Floor: Full Bathroom w/ Shower/Tub Combo<br>-2nd Floor: Full Bathroom w/ Shower<br>Other Amenities<br>-Fully Equipped Kitchen<br>-Window A/C in Bedrooms<br>-Fireplace is NOT for guest use (fines remitted)<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV w/ streaming<br>-Washer/Dryer (1st floor)<br>-Deck with Outdoor Dining<br>-Fire Pit<br>-Outdoor Shower<br>-Private Yard<br>-NO Pets (fines remitted)<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0370382240

14478 - Marine Dream: Quintessential Captain’s House w/ Water Views! **Note: Pictured Dock will not be available for the 2026 season - new dock will be available in 2027** Immerse yourself in the quintessential Cape Cod experience at Marine Dream, nestled in the heart of Eastham, the Gateway to the National Seashore. This majestic retreat beckons families and friends alike to savor the charm and allure of Cape Cod. <br>Upon entering, you’re greeted by a sprawling open-concept layout seamlessly merging kitchen, dining, and living spaces, ideal for hosting gatherings. Adorned with expansive windows framing picturesque ocean vistas, this home exudes serenity and tranquility. Step outside onto the grand patio, complete with a gas grill, overlooking a lush lawn leading to the azure cove—a haven for summer BBQs and al fresco dining.<br><br>Entertainment abounds within the sunlit second living area, offering a haven for relaxation or spirited board game nights. The vast manicured lawn invites outdoor adventures, while nearby attractions like Nauset Light Beach and Skaket Beach promise endless seaside delights.<br><br>Though the property shares its expansive lawn with neighboring cottages, there’s no shortage of space for recreation and enjoyment. Revel in the proximity to Cape Cod’s natural wonders, from the National Seashore to the scenic Cape Cod Rail Trail, perfect for biking and hiking enthusiasts. Grab a delectable burger and milkshake at the nearby Knack, or enjoy an elevated brunch at Brine.<br><br>Marine Dream epitomizes luxury, comfort, and entertainment, promising an unforgettable Cape Cod getaway. Embrace the allure of Eastham and reserve your slice of paradise today at the Marine Dream!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 11<br>Bedrooms<br>-Total: 5<br>-Bedroom #1: 1 King Bed with En Suite Full Bathroom, 1st Floor<br>-Bedroom #2: 1 Queen Bed, 1st Floor<br>-Bedroom #3: 1 King Bed with En Suite Full Bathroom, 2nd Floor <br>-Bedroom #4: 1 Queen Murphy Bed, 2nd Floor<br>-Bedroom #5: 3 Twin Beds, 2nd Floor <br>Bathrooms<br>Total: 4<br>-Bathroom #1: En Suite Full Bathroom with Jetted Tub and Shower, 1st Floor<br>-Bathroom #2: Full Bathroom with Shower, 1st Floor<br>-Bathroom #3: En Suite Full Bathroom with Tub/Shower Combo, 2nd Floor<br>-Bathroom #4: Full Bathroom with Shower, 2nd Floor<br>Other Amenities<br>-Central A/C<br>-Smart Lock/Self Check-In<br>-WiFi<br>-TV with Cable<br>-Washer and Dryer (1st Floor)<br>*please note outdoor amenities are seasonal*<br>-Patio with Outdoor Dining<br>-4 SUPs<br>-1 Canoe <br>-1 Kayak<br>-6 Life Vests<br>-Outdoor Ping Pong <br>-Corn Hole & other lawn games<br>-Gas Grill<br>-Please note there are steep steps leading to the 2nd Floor<br>-Views of Town Cove<br>-Sheets and Bath Towels Provided<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 3 cars maximum<br>-C0411990860

14480 - Fore and Aft: Newly updated spacious steps to water! **Note: Pictured Dock will not be available for the 2026 season - new dock will be available in 2027** Nestled between modern farmhouse charm and traditional seaside allure, this quaint abode exudes a sense of luminous tranquility with breathtaking views of the nearby ocean cove just steps away across the verdant lawn. Adorned with a spacious farmer’s porch, it offers the quintessential setting for unwinding with a refreshing drink and immersing oneself in the timeless allure of summer. <br>The first floor unfolds with an inviting openness, featuring an updated kitchen, a cozy living area replete with comfortable seating and a TV for entertainment, and a dining table ideal for savoring delectable meals. Tucked away behind the kitchen, a conveniently located bathroom adds to the home’s practicality and comfort.<br><br>Upstairs, two generously sized bedrooms beckon with queen beds and en suite bathrooms, ensuring utmost privacy and convenience for guests. While one bedroom boasts captivating ocean views, the other is equally inviting, both adorned with ample windows that bathe the rooms in natural light.<br><br>With ample space for four guests, this retreat offers an idyllic sanctuary to start the day with a steaming cup of coffee amidst the warmth of a summer morning or unwind with a cocktail while marveling at the hues of a breathtaking sunset. Whether embracing the serenity of dawn or the enchantment of dusk, this charming home promises an unforgettable coastal getaway filled with blissful moments and cherished memories.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 4<br>-2 floors<br>Bedrooms<br>-Total: 2<br>-2nd Floor Master Bedroom: 1 Queen Bed w/ En-suite<br>-2nd Floor Bedroom #2: 1 Queen Bed w/ En-suite<br>Bathrooms<br>Total: 2.5<br>-1st floor half bath<br>-2nd Floor Ensuite<br>-2nd Floor Ensuite<br>Other Amenities<br>-Central A/C<br>-Cable TV<br>-WIFI<br>-Washer/Dryer (in basement)<br>-4 SUPs<br>-1 Canoe <br>-1 Kayak<br>-6 Life Vests<br>-Outdoor Ping Pong<br>-Corn Hole & other lawn games<br>-Fire Pit<br>-Please note outdoor amenities are seasonal<br>-Water views and steps from water<br>-Sheets and bath towels provided<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for a maximum of 2 cars<br>-C0412010860

Cozy Orleans one bedroom bungalow in historic Rock Harbor. Immaculately restored with granite counters and beautiful hardwood floors, tile bath, and high quality construction. Set within the tranquil beauty of Rock Harbor Creek and just 0.2 miles to Rock Harbor & Cape Cod Bay and .9 miles to the Cape Cod Rail Trail. The fully equipped kitchen with new appliances for 2026 is open to the dining nook and living room. Cozy bedroom with new king bed, large closet, en-suite bathroom w/walk-in shower and stacked washer/dryer. In the living room there’s a queen sleep sofa, TV and desk. The back yard has a picnic table and grill for summer cookouts and an outdoor shower. Two Kayaks available for guest use. **Blankets and Pillows are provided, but you will need to bring or rent sheets and towels**

15578 - The Salty Hare: Short drive to town and popular beaches! Truly in the heart of Orleans, right around the corner from the Cape Cod Rail Trail (less than a mile), and only a whisper away from the coveted shores of Skaket Beach, The Salty Hare beckons with timeless allure. This tastefully restored home exudes an aura of coastal elegance, and promises a rejuvenating escape from the bustle of everyday life.&lt;br&gt;&lt;br&gt;Step inside to discover a harmonious blend of historic charm and contemporary comfort. The updated kitchen, a culinary haven bathed in natural light, invites delicious creations, while the cozy wrap-around deck offers an idyllic setting for savoring morning coffee amidst lush greenery.&lt;br&gt;&lt;br&gt;Indulge in moments of relaxation in the deep claw-foot tub of the tiled bathroom, a sanctuary where old-world elegance meets modern convenience. For balmy summer days, rejoice in the recent addition of mini splits, ensuring optimal comfort year-round.&lt;br&gt;&lt;br&gt;Venture just minutes away to Skaket Beach, where the sun-kissed sands set the stage for leisurely strolls and sunset soirées. Upon returning, immerse yourself in the serenity of the outdoor shower, enveloped by the splendor of nature.&lt;br&gt;&lt;br&gt;As evening descends, embrace the art of outdoor living on the back deck, where barbecues unfold against a backdrop of birdsong and rustling leaves. With an array of dining options mere minutes away, including the acclaimed Hog Island Brewery and The Beacon Room, culinary delights are always within reach.&lt;br&gt;&lt;br&gt;Whether seeking seaside serenity or vibrant local experiences, The Salty Hare offers an unparalleled retreat, where every moment is infused with coastal charm and cherished memories await.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 8&lt;br&gt;Bedrooms&lt;<br&gt;-Total 4&lt;br&gt;-1st Floor Bedroom: 1 Daybed w/ Trundle (2 Twins) and en suite Full Bathroom&lt;br&gt;-2nd Floor Bedroom: 1 King Bed (pass through to twins room)&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom: 2 Twin Beds (pass through from king bedroom)&lt;br&gt;Bathrooms&lt;br&gt;-Total 2&lt;br&gt;-1st Floor: Full Bathroom w/ Shower (en suite Daybed/Trundle Bedroom)&lt;br&gt;-2nd Floor: Full Bathroom w/ Tub and handheld shower head&lt;br&gt;Other Amenities&lt;br&gt;-Split AC System&lt;br&gt;-WiFi&lt;br&gt;-Smart TV&lt;br&gt;-Washer/Dryer&lt;br&gt;-Propane Grill&lt;br&gt;-Outdoor Shower&lt;br&gt;-Indoor Fireplaces are not for guest use (fines remitted)&lt;br&gt;-Please note outdoor amenities are available seasonally&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;-Parking for 3 cars maximum&lt;br&gt;-C0481762240 License number: C0481762240

14477 - The Captains Estate: Waterfront Fun at this Huge Family Estate! **Note: Pictured Dock will not be available for the 2026 season - new dock will be available in 2027** Indulge in the ultimate group getaway at this exceptional property, comprising four distinct homes for exclusive use, perfect for hosting a family reunion or a rejuvenating yoga retreat. Nestled along the tranquil shores of Town Cove, this haven offers a harmonious blend of communal spaces and private sanctuaries, ensuring that every guest can find their ideal balance of togetherness and solitude.&lt;br&gt;&lt;br&gt;Step outside to discover a sprawling private yard, beckoning with the promise of leisurely afternoons spent paddle boarding on the glistening waters or engaging in spirited lawn games beneath the azure sky. As twilight descends, gather around the grill for alfresco feasts under a canopy of twinkling stars, creating cherished memories amidst the serenity of nature.&lt;br&gt;&lt;br&gt;Despite its secluded ambiance, this retreat remains conveniently positioned, facilitating effortless exploration of Cape Cod’s myriad attractions. Arrange for a private boat charter to whisk you away from your very own dock, embarking on exhilarating adventures to the Outer Beach and the mesmerizing vistas of the National Seashore (Please note: dock availability may be seasonal, and removed post-Labor Day).&lt;br&gt;&lt;br&gt;Within the confines of this enchanting compound, modern amenities abound, from WiFi and cable TV to central A/C and washer/dryer facilities, ensuring a seamless blend of comfort and convenience throughout your stay. Fresh linens and bath towels are provided, alleviating the need for cumbersome packing and allowing you to fully immerse yourself in the joys of vacation living.&lt;br&gt;&lt;br&gt;Don’t let this opportunity slip away – seize the chance to reserve this exquisite compound for your next Cape Cod escape, where cherished moments await amidst the beauty and tranquility of coastal living.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 23&lt;br&gt;-Walk to Town&lt;br&gt;- 4 Units in 1! (Main House 1, Cottage 2, Cottage 3 & Cottage 4)&lt;br&gt;Bedrooms&lt;br&gt;-Total: 11&lt;br&gt;Main House 1:&lt;br&gt;-1st Floor Master Bedroom: 1 King Bed w/ En-suite&lt;br&gt;-1st Floor Bedroom #2: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom #1: 1 King Bed w/ En-suite&lt;br&gt;-2nd Floor Bedroom #2: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom #3: 3 Twin Beds&lt;br&gt;Cottage 2:&lt;br&gt;-2nd Floor Master Bedroom: 1 Queen Bed&lt;br&gt;Cottage 3:&lt;br&gt;-2nd Floor Master Bedroom: 1 Queen Bed w/ En-suite&lt;br&gt;-2nd Floor Bedroom #2: 1 Queen Bed w/ En-suite&lt;br&gt;Cottage 4:&lt;br&gt;-1st Floor Master Bedroom: 1 Queen Bed&lt;br&gt;-1st Floor Bedroom #2: 2 Twin Beds&lt;br&gt;-2nd Floor Bedroom #1: 2 Twin Beds&lt;br&gt;Bathrooms&lt;br&gt;-Total: 8.5&lt;br&gt;Main House 1:&lt;br&gt;-Bathroom #1: En Suite Full Bathroom with Jetted Tub and Shower, 1st Floor&lt;br&gt;-Bathroom #2: Full Bathroom with Shower, 1st Floor&lt;br&gt;-Bathroom #3: En Suite Full Bathroom with Tub/Shower Combo, 2nd Floor&lt;br&gt;-Bathroom #4: Full Bathroom with Shower, 2nd Floor&lt;br&gt;-Please note there are steep steps leading to the 2nd Floor&lt;br&gt;Cottage 2:&lt;br&gt;-Bathroom: 1st floor, full bath tub/shower combo&lt;br&gt;Cottage 3:&lt;br&gt;-Bathroom #1: 2nd floor, full bathroom, En-Suite&lt;br&gt;-Bathroom #2: 2nd floor, full bathroom, En-Suite&lt;br&gt;-Bathroom #3: 1st floor, half bathroom&lt;br&gt;Cottage 4:&lt;br&gt;-Bathroom #1: 1st floor, full bathroom&lt;br&gt;-Please note there are steep steps leading to the 2nd Floor&lt;br&gt;Other Amenities&lt;br&gt;-Waterfront&lt;br&gt;-Walk to Water&lt;br&gt;-Water Views&lt;br&gt;-Walk to Town&lt;br&gt;-Central & Split A/C Units&lt;br&gt;-Smart TV/Cable TV&lt;br&gt;-WiFi&lt;br&gt;-Washer/Dryer (Main House & Cottage 3)&lt;br&gt;-Jetted Tub (Main House)&lt;br&gt;-Outdoor Shower (Cottage 4)&lt;br&gt;-Outdoor Ping Pong&lt;br&gt;-Corn Hole & Lawn Games&lt;br&gt;-Private Yard&lt;br&gt;-Gas Grill&lt;br&gt;-4 SUP Boards &lt;br&gt;-1 Canoe&lt;br&gt;-1 Kayak&lt;br&gt;-6 Life Vests&lt;br&gt;-Please note outdoor amenities are available seasonally&lt;br&gt;-There is parking for a maximum of 8 cars at this home&lt;br&gt;-Sheets and Bath Towels Provided with Beds Made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;-Please note this property is not available as a venue per town zoning laws&lt;br&gt;-C041471086

14479 - Lifeboat Lights: Cute Cottage Living by the Sea! **Note: Pictured Dock will not be available for the 2026 season - new dock will be available in 2027** Nestled within a charming enclave of four homes, each boasting its own private outdoor sanctuary and mesmerizing water vistas, this delightful abode offers the quintessential Cape Cod summer experience. Step into the welcoming ambiance of the first floor, where a cozy kitchen with a quaint eat-in area seamlessly transitions into a living room adorned with exposed beams and wide pine floors. Relax on the sofa and catch glimpses of the tranquil waters, allowing yourself to be swept away on a maritime-inspired escape. &lt;br&gt;Adjacent to the living area, a full bathroom awaits, complete with all the essentials for your comfort. Ascend the stairs to the master bedroom, where abundant space and expansive windows beckon you to unwind amidst serene views of the cove and lush lawn below. Despite its cozy dimensions, this retreat comfortably accommodates two guests, offering a perfect haven for summer adventures in Cape Cod.&lt;br&gt;&lt;br&gt;Indulge in outdoor grilling on the deck, lounge on the expansive lawn, or venture to the nearby beach for sun-kissed days by the shore. Return home to your charming oasis and bask in the soothing rhythm of the waterfront, whether you’re watching boats glide by or savoring a breathtaking sunrise from the comfort of your bed. Embrace the essence of Cape Cod living at this idyllic retreat, where every moment is infused with seaside serenity and timeless charm.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 2&lt;br&gt;-2 floors&lt;br&gt;Bedrooms&lt;br&gt;Total: 1&lt;br&gt;-1 queen bed, 2nd floor&lt;br&gt;Bathrooms&lt;br&gt;Total: 1&lt;br&gt;-1st floor tub/shower combo&lt;br&gt;Other Amenities&lt;br&gt;-Split A/C (similar to central A/C)&lt;br&gt;-Smart/Cable TV&lt;br&gt;-WIFI&lt;br&gt;-Gas grill&lt;br&gt;-Please note outdoor amenities are seasonal&lt;br&gt;-4 SUPs&lt;br&gt;-1 Canoe &lt;br&gt;-1 Kayak&lt;br&gt;-6 Life Vests&lt;br&gt;-Outdoor Ping Pong&lt;br&gt;-Corn Hole & other lawn games&lt;br&gt;&lt;br&gt;-Water views/Waterfront&lt;br&gt;-Sheets and bath towels provided&lt;br&gt;-Cleaned with hospital grade disinfectant&lt;br&gt;-Parking for a maximum of 2 cars&lt;br&gt;-C0412000860

14481 - Pilot’s Edge: Waterfront amazing views near beaches! **Note: Pictured Dock will not be available for the 2026 season - new dock will be available in 2027** &lt;br&gt;&lt;br&gt;You can’t really get more waterfront than this! Imagine sitting on the deck, the water lapping up toward you, sipping your favorite drink and soaking up the sun. Here, the cove feels like part of the home itself stretching beyond the deck, shimmering through the kitchen windows, and setting the pace for easy Cape Cod days spent outside from morning to sunset.&lt;br&gt;&lt;br&gt;Inside, the first floor features an eat-in kitchen with beautiful water views, an inviting living area with large cove-facing windows, a queen bedroom, a second bedroom with two twin beds, and a full bathroom with a shower. Upstairs, offers a rustic, unfinished loft-style sleeping area with two twin beds - a fun hideaway for kids or adventurous guests, with windows that make you feel almost suspended above the water.&lt;br&gt;&lt;br&gt;Outside is where this home truly shines. Sip coffee on the deck, rinse off in the outdoor shower, launch a paddle board, kayak, or canoe, or spend the afternoon playing ping pong, corn hole, and other lawn games by the water. With 4 SUPs, 1 canoe, 1 kayak, 6 life vests, WiFi, cable TV, window A/C, and dog-friendly accommodations, it has everything you need for a carefree coastal escape. Please note all paddle boards, canoes, kayaks, ping pong, corn hole, and other lawn games are shared between all four cottages on the compound.&lt;br&gt;&lt;br&gt;Spend your days paddling the calm cove, soaking up the sun, and letting the tide decide the rhythm of your vacation. With waterfront living like this, you won’t want to go back home. &lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 6&lt;br&gt;-2 floors&lt;br&gt;Bedrooms&lt;br&gt;-Total 3&lt;br&gt;-1st Floor Master Bedroom: 1 Queen Bed&lt;br&gt;-1st Floor Bedroom: 2 Twin Beds&lt;br&gt;-2nd Floor Bedroom: 2 Twin Beds&lt;br&gt;-Please note there are steep steps leading to the 2nd Floor&lt;br&gt;Bathroom&lt;br&gt;-Total 1&lt;br&gt;-1st Floor: Full Bathroom w/ Shower&lt;br&gt;Other Amenities&lt;br&gt;-Window A/C&lt;br&gt;-TV&lt;br&gt;-WiFi&lt;br&gt;-Outdoor Shower&lt;br&gt;-Wood Fire Pit&lt;br&gt;-4 SUPs&lt;br&gt;-1 Canoe&lt;br&gt;-1 Kayak&lt;br&gt;-6 Life Vests&lt;br&gt;-Outdoor Ping Pong&lt;br&gt;-Corn Hole & other lawn games&lt;br&gt;-Paddle boards, canoes, kayaks, ping pong, corn hole, and other lawn games are shared between all four cottages on the compound&lt;br&gt;-Waterfront&lt;br&gt;-Indoor Fireplaces are not for guest use (fines remitted) &lt;br&gt;-Sheets and bath towels provided&lt;br&gt;-Cleaned with hospital grade disinfectant&lt;br&gt;-Parking for 2 cars maximum&lt;br&gt;C0414750860

15517 - Endless Summer: Private pool 3 mins to Skaket Beach! Imagine long afternoons by the pool, evenings spent playing games with family and friends, cocktails in the upstairs bar and game room, and plenty of room for everyone to spread out and relax. With 3,500 square feet of living space, four bedrooms, and a sprawling private backyard, Endless Summer is the perfect home base for your Cape Cod getaway.&lt;br&gt;&lt;br&gt;The outdoor space is the true highlight of this home, featuring a private pool, spacious patio with plenty of seating, gas grill, outdoor shower, and a large lawn for corn hole, yard games, or simply soaking up the sunshine. When you’re ready for the beach, Skaket Beach is just a three-minute drive away. You’ll also be minutes from Nauset Beach, Rock Harbor, Hog Island Brewery, Rock Harbor Grill, Orleans Bowling Center, and other local favorites, making it easy to enjoy everything from beach days and fresh seafood to breweries and family-friendly entertainment.&lt;br&gt;&lt;br&gt;Inside, the first floor features a fully equipped kitchen, comfortable living room, a king primary suite with an updated en suite bath, a second bedroom with a twin bed, and an additional half bath. Upstairs, you’ll find two more bedrooms—one with two queen beds and another with a full bed and twin bunk beds—plus a spacious lounge and game room above the garage complete with a built-in bar. Central A/C, WiFi, cable TV, and a washer and dryer provide all the comforts of home.&lt;br&gt;&lt;br&gt;Whether you’re challenging the family to a ping pong tournament, gathering around the board games after dinner, or unwinding by the pool under the stars, Endless Summer is the kind of place where lasting vacation memories are made. Reserve your Orleans getaway today and experience the very best of Cape Cod.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-No Pets (fines remitted)&lt;br&gt;-Sleeps 10&lt;br&gt;-2 Floors&lt;br&gt;Bedrooms&lt;br&gt;-Total 4&lt;br&gt;-1st Floor Bedroom: King Bed w/ en suite Full Bathroom&lt;br&gt;-1st Floor Bedroom: Twin Bed&lt;br&gt;-2nd Floor Bedroom: 2 Queen Beds&lt;br&gt;-2nd Floor Bedroom: 1 Full Bed and 1 Bunk Bed (2 Twins)&lt;br&gt;Bathrooms&lt;br&gt;-Total 2.5&lt;br&gt;-1st Floor: Half Bathroom&lt;br&gt;-1st Floor: Full Bathroom w/ Shower (en suite King Bedroom)&lt;br&gt;-2nd Floor: Full Bathroom w/ Shower/Tub combo&lt;br&gt;Other Amenities&lt;br&gt;-Central A/C + Split A/C in game room&lt;br&gt;-TV&lt;br&gt;-WiFi&lt;br&gt;-Washer/Dryer&lt;br&gt;-Bar/Game Room&lt;br&gt;-Outdoor shower&lt;br&gt;-Private Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)&lt;br&gt;-Large private yard&lt;br&gt;-Gas grill&lt;br&gt;-Minutes from Skaket Beach&lt;br&gt;-Please note outdoor amenities are available seasonally&lt;br&gt;-Sheets and bath towels provided with beds made upon arrival&lt;br&gt;-Cleaned with hospital grade disinfectant&lt;br&gt;-Parking for 4 cars maximum&lt;br&gt;C0425922240