Large group vacation rentals in Truro, MA

12220 - Hilltop Hideaway: Beautiful Water Views Dogs Welcome! Escape to your secluded haven atop the Truro hills - behold the Hilltop Hideaway, your gateway to an unforgettable Outer Cape retreat! Elevated above the norm, this spacious abode offers sweeping panoramas of Pamet Harbor, Cape Cod Bay, and the charming silhouette of Provincetown on the horizon.<br><br>Step inside this two-story sanctuary, where the heart of the home beckons with an open kitchen boasting expansive countertops and corner windows framing mesmerizing water vistas. Adjacent, the dining area invites you to savor every meal amidst breathtaking scenery, while a cozy family room promises relaxation and cherished moments. Retreat to the primary bedroom on the main floor, offering a king-size bed and a full bathroom directly across the hall for ultimate comfort. Ascend upstairs to discover additional bedrooms, including a queen-size bed and twin accommodations perfect for young adventurers.<br><br>Venture outdoors to the back deck, where you’ll be mesmerized by waterfront sunsets peeking through the trees. Just a four minute drive will bring to you the nearby beach. After a day of adventures, unwind with a drink under the stars or gather around the fire pit for indulgent s’mores, enveloped in the tranquility of your natural surroundings.<br><br>Complete with convenient amenities such as a washer and dryer, propane grill, and refreshing outdoor shower, your stay at the Hilltop Hideaway promises relaxation and rejuvenation. Embrace the serenity of Truro’s scenic landscapes while still enjoying easy access to the vibrant dining, nightlife, and shopping of nearby Provincetown. Experience the best of both worlds at your Hilltop Hideaway - where memories are made and tranquility reigns supreme.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>-2 Floors (1st Floor + 2nd Floor)<br>Bedrooms<br>-Total: 4<br>-1st Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 2 Twin Beds (Twin Bed w/ Twin Trundle)<br>-2nd Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total: 2.5<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom w/ Shower/Tub combo<br>-2nd Floor: Full Bathroom w/ Shower<br>Other Amenities<br>-Window A/C Units<br>-WiFi<br>-Smart TV with Streaming<br>-Washer and Dryer (ground floor)<br>-Foosball<br>-Gas Grill<br>-Fire Pit<br>-Deck with Furniture<br>-Outdoor Shower<br>-please note outdoor amenities are available seasonally<br>-Indoor Fireplaces are not for guest use (fines remitted)<br>-Parking is available for a maximum of 4 cars<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-C0413513000

12202 - Great Hollow: Walk to Beach! Central AC! This beautifully updated architectural home is situated just a short walk to the stunning Great Hollow Beach perched above the hilltops of Truro. <br><br>You can watch the fireworks in Provincetown from one of many decks! The best eateries in Truro and P-town and the National Seashore beaches are just a 10 minute drive away. You’ll love this quiet and private neighborhood. This modern style home with windows everywhere provides endless views of the Truro Hills! <br><br>The outdoor space at this home is phenomenal, offering a raised outdoor shower, gas grill, covered deck area, two other open deck areas, and a roof-level deck with amazing views. <br><br>The first floor of this home offers a large living and kitchen area with a beautiful and bright sunken dining room. The first floor also offers a half bathroom as well as a bedroom with a queen size bed. The second floor offers a lofted seating area with access to the upper decks with have amazing views as well as a master bedroom with a queen size bed and en suite bathroom. The ground level basement area of the home offers a another full bathroom as well as two bedrooms; the first bedroom contains 1 queen bed and the other contains two twin beds as well as a twin bunk bed (4 twins total). The basement also offers a laundry area with a washer and dryer. This home has been recently updated with a brand new central AC system. <br><br>Great Hollow Beach is just a 5 minute walk from the doorstep which makes this home perfect for conveniently enjoying a great beach day! This home and location are sure to delight and offer a perfect spot for a spectacular Cape Cod vacation!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 10<br>-3 Floors<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 Queen Bed<br>-2nd Floor Master Bedroom: 1 Queen Bed w/ en suite Full Bathroom<br>-Ground Floor Bedroom: 1 Queen Bed<br>-Ground Floor Bedroom: 4 Twin Beds (1 bunk bed)<br>Bathrooms<br>-Total 2.5<br>-1st Floor: Half Bathroom<br>-2nd Floor: Full Bathroom w/ Shower (en suite Queen Bedroom)<br>-Ground Floor: Full Bathroom w/ Shower/Tub combo<br>Other Amenities<br>-Central AC<br>-WiFi<br>-TV<br>-Washer/dryer on ground level<br>-Wood Stove Not for Guest Use (Fines Remitted)<br>-Outdoor shower<br>-Private yard<br>-Several deck areas and roof-level deck<br>-5 min walk to amazing Great Hollow Beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0419093000

12230 - Love Shack: Stylistic Home and Easy Walk to the Beach! Lovingly decorated by an award winning rock artist, this retro inspired home awaits you in the seaside town of Truro. You’ll enjoy the history and aesthetics of Love Shack, and love the short walk to the northside of Great Hollow Beach. Concealed from the roadside, set way back, this architectural gem unveils itself as a spacious retreat, beckoning guests to indulge in its tranquil ambiance. Step inside to discover a haven of comfort where every detail has been meticulously crafted to evoke a sense of nostalgia and fun. It’s a great place to get together! Ideal for families seeking a beachside getaway, Love Shack offers ample space for everyone to unwind and create lasting memories. Spend your days basking in the sun on the expansive back deck, savoring breakfast al fresco, or sipping your morning coffee amidst the gentle ocean breeze. The outdoor shower makes it easy to rinse away the sand after a day by the beach. Inside, the open kitchen and dining area provide a welcoming space for gatherings, while the Smart TV streaming ensures endless entertainment options for the whole family. Venture upstairs via a wide 8-step staircase to find two of the three bedrooms, each exuding its own unique charm and comfort. Please note, that this home primarily features a single-level layout, with the half staircase providing access to additional sleeping quarters. Love Shack boasts an enviable location, with the north side of Great Hollow Beach just 0.3 miles away, offering easy access to sun, sand, and surf. For those craving further exploration, a short drive leads to various bayside beaches waiting to be discovered-- less than 15 miles down the road. Convenience is key at this vacation destination with local amenities such as Box Lunch, your go-to spot for beachside sandwiches, and Truro Vineyards, perfect for an evening of wine tasting or dining out, just a short drive away. Escape to Love Shack and experience the ultimate coastal retreat with a touch of rock history. Home Details: -No Pets(Fines Remitted) -Sleeps 6 Bedrooms -Total 3 -1st Floor Bedroom: 1 King Bed -1st Floor Bedroom: 1 Queen Bed -1st Floor Bedroom: 2 Twin Beds Bathrooms -Total 2 -1st Floor: Tub/Shower Combo -1st Floor: Shower Other Amenities -Split System for AC and Heat in Master Bedroom and living areas -Floor Unit AC in secondary bedrooms -WiFi -Smart TV w/Streaming -Washer/Dryer -Propane Grill -Indoor Fireplace is not for guest use(fines remitted) -Outdoor Shower -Please note outdoor amenities are available seasonally -Sheets and Bath Towels Provided with Beds made Upon Arrival -Cleaned with Hospital Grade Disinfectant -Parking for 2 cars maximum -C0348293000

12226 - Aqua Oasis: Beautiful backyard, pool, deeded beach rights! Tucked away in Truro, with neighborhood association access to Tru Haven Beach, this vacation home promises an idyllic escape. Situated within a quaint neighborhood, this beach gem is a mere 2-minute drive or a leisurely 15-minute stroll from your doorstep, with the convenience of a drop-off area too (please note, parking is not available) and a private staircase leading you to the sandy shores. <br><br>Designed with unique flair by the renowned architect Alan Dodge, this home exudes personality and character. Thoughtful touches and eclectic Truro-style furnishings create a space that feels both unique and welcoming - perfect for accommodating multi-generational families. The first floor features a king bedroom with an en suite bathroom, while upstairs offers two queen bedrooms (one with an en suit bathroom), a bedroom with two twin beds, and an additional full bathroom. <br><br>While here, relish in the pleasures of a private pool where your family will share priceless memories they will replay while daydreaming of future stays (please, no dogs in the pool area). The expansive patio invites you to fire up the grill and take in the salt air with peek-a-boo views of Cape Cod Bay and Provincetown. As the sun begins to dip below the horizon, savor your favorite cocktails on the second-floor deck accessible from two bedrooms, offering even more breathtaking water vistas.<br><br>For those quintessential evening activities, our designated sand area boasts a fire pit, perfect for marshmallow roasting, with ample seating for everyone to sit back and relax.<br><br>When the culinary delights of Cape Cod beckon, you’re in for a treat. The Box Lunch is your go-to spot for scrumptious beach sandwiches, while Truro Vineyards, a short jaunt from your home, offers the perfect afternoon of wine tasting. These Cape Cod staples are both conveniently less than a mile away!<br><br>Escape to a one-of-a-kind vacation retreat, where Truro’s beauty and charm come to life. Your adventure begins here.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>-2 Floors<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 King Bed w/ en suite Bathroom<br>-2nd Floor Bedroom: 1 Queen Bed w/ en suite Bathroom <br>-2nd Floor Bedroom: 1 Queen Bed <br>-2nd Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total 3.5<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom w/ Shower and Soaking Tub (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower<br>Other Amenities <br>-Private Heated Pool (Only guaranteed to be open Memorial Day - Labor Day)<br>-Outdoor Shower<br>-Central AC<br>-Electric Fireplace available for guest use<br>-WiFi<br>-TV<br>-Washer/Dryer<br>-Propane Grill <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>C0455953000

12214 - Oyster Oasis: Beachfront on Private Beach w/ AC! Panoramic bay views will take your breath away at this Truro home, perched on the dunes as close to the water as you can imagine. Welcome to the Oyster Oasis! Pushing open the navy blue front door, you’re greeted by breathtaking views as you step into the open concept kitchen and living room. Enjoy breakfast at the large center Island as you stare over Cape Cod Bay with views of Pilgrim Monument in the distance. Down the hallway, three bedrooms complete the sleeping arrangements in this sleeps 6 home. The first two bedrooms at the front of the home each have a king bed and beautiful built-in cabinetry. Further down the hall, the final bedroom houses two twin beds atop great built-in storage, and breathtaking views of the bay waters below. The views are even better on the sprawling back deck, where you may even fall asleep in the Adirondack chairs as you listen to the waves lap against the shore. The crushed bluestone patio area surrounding the whole house provides plenty of great space to soak in the sun while the small cedar tree adds just the right amount of shade to your sand-dune hideaway with the table underneath offering a great spot for outdoor dining. Be sure to plan a few nights to be at this incredible home during sunset, a near spiritual experience at the end of your vacation days with its breathtaking beauty. Just to the left of the driveway is a pathway and staircase that leads directly down to the beach. You could quite literally roll out of bed onto the sand at Great Hollow beach! Beyond the beauty of this home and the beach below, you’ll be close to restaurants, shops, and stores of all types. Between the location, views, and amenities, this immaculate home is one-of-a-kind, and you surely don’t miss this chance to enjoy a classic Cape Cod beach house by the bay. Enjoy your next vacation at the Oyster Oasis. Home Details: -Sleeps 6 -Single Floor Bedrooms -Total 3 -1st Floor Bedroom: 1 King Bed -1st Floor Bedroom: 1 King Bed -1st Floor Bedroom: 2 Twin Beds Bathrooms -Total 1 -1st Floor: Full Bathroom w/ Shower Other Amenities -Central A/C and Heating -WiFi -Smart Lock/ Self Check-In -Smart TV -Propane Grill -Deck with Outdoor Dining and Lounging -Outdoor Shower -Laundry is available in the garage, Memorial Day-Labor Day. -Bay Views -Walk to the Beach -NO PETS (fines remitted) -Sheets and Bath Towels Provided with Beds made Upon Arrival -Cleaned with Hospital Grade Disinfectant C0056263000

13350 - Happy Haven: Huge Deck Perfect for Lounging w Sweeping Views! This comfortable and secluded four bedroom vacation home, located on a marsh just outside of the downtown Wellfleet area, offers the perfect balance between privacy and convenience. From this peaceful, secluded location, you will enjoy sweeping views of the marsh and all of its natural beauty. Travel just over a mile from the property to quaint downtown Wellfleet, an area full of character and friendly charm, where you will find a vast array of browsing, dining, picture-taking and sightseeing opportunities within a relatively short walk, not to mention the magnificent Wellfleet Harbor with a constantly changing panorama of sailboats, motor yachts, sport fishing boats and trawlers. Mayo Beach, an excellent family beach located on the harbor with stunning views of Great Island and Indian Neck, as well as Bound Brook Island Beach, one of the most spectacular, secluded spots on the Cape, are both within a few miles of the property. <br><br>This amazing property features a newly updated and furnished four bedroom home that sleeps ten guests total with 1,585 square feet of living space. On the main floor, you will find a spacious living room with comfortable sofa and armchair seating and a wall of large windows and sliding doors that lead to a deck overlooking the beautiful marsh and surrounding nature. The formal dining area and fully equipped kitchen have everything you will need during your stay. There is one bedroom on the main floor, the master with a king bed and beautiful views of the marsh through the sliding door that leads to the deck. A full bathroom and a half bathroom round out the first floor. The remaining three bedrooms are located on the second floor and include two bedrooms with a queen bed and a twin bed, and another with two twin beds, in addition to another full bathroom. <br><br>There is a “game room” downstairs in the unfinished basement area, including games such as ping pong, darts, and bumper pool, and if you need to do laundry during your stay, there is a washer and dryer available for use. Other amenities include a smart lock for self check-in and easy access throughout your stay, window A/C units in the bedrooms to keep you and your guests comfortable during the hot summer weather, WiFi, apple TV, a propane grill, and sheets and bath towels provided to all guests with beds made upon arrival. This home is also dog friendly, so don’t forget to bring along your pup!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 10<br>-2 Floors<br>-1,585 Sq Ft<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 2 Twin Beds<br>-2nd Floor Bedroom: 1 Queen Bed + 1 Twin Bed<br>-2nd Floor Bedroom: 1 Queen Bed + 1 Twin Bed<br>Bathrooms<br>-Total 2.5<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom w/ Tub/Shower Combo<br>-2nd Floor: Full Bathroom w/ Shower<br>Other Amenities<br>-Fully Equipped Kitchen w/ Dishwasher<br>-Smart Lock/Self Check-In<br>-Window A/C Units in Bedrooms<br>-WiFi<br>-Apple TV<br>-Ping Pong/Darts/Bumper Pool (unfinished basement)<br>-Washer/Dryer (unfinished basement)<br>-Newly Built Deck w/ Furniture<br>-Propane Grill<br>-Sweeping Views of the Marsh<br>-Close to Downtown Wellfleet<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0413133180

13349 - Pine Valley: Private Location w/ Guest House! Hidden down a private dirt road in the heart of Wellfleet sits Pine Valley, a unique 3 bedroom home with separate 1 bedroom/1 bath guest house cottage. Perfect for a multiple family vacation, this property features a wrap-around deck, two outdoor showers, a jacuzzi tub in the master bedroom of the main house and a screened in porch on the guest house.<br><br>This home is conveniently situated between the Atlantic Ocean and Cape Cod Bay which means the toughest choice of your vacation might be whether to spend your days in the sun on the bay at Mayo Beach (2.2 miles) or on the Atlantic Ocean at Cahoon Hollow Beach–home of the world famous Beachcomber restaurant and bar (2.7 miles). Long Pond is also nearby (1.1 miles) if you have small children or are just in the mood for some freshwater!<br><br>Entering Pine Valley you’ll find the kitchen, a half bathroom with washer/dryer, and open living and dining area with access through multiple slider doors to the wrap around deck. Upstairs is the Master bedroom with Queen bed and en-suite bathroom with shower and jacuzzi tub. There is also a bonus twin daybed and desk area on the second floor landing which is open to the lower level. <br><br>Downstairs there is a full bathroom and two bedrooms–one with two Twin size beds and one with a Queen size bed. The adjacent guest house has a living room, small kitchen and full bathroom on the first floor with a Queen size bedroom on the second floor.<br><br>Outside Pine Valley there is a wrap around deck with plenty of room to relax and grill with a nice view of the whole property. There is a separate second floor balcony as well on the main house which has a fantastic feeling of elevation and is elevated from the main deck for a bit of privacy. The guest house has a screened in porch with furniture and both buildings have an outdoor shower outside.<br><br>Wellfleet is also home to a variety of excellent places to eat and drink. Head to the Wellfleet pier (1.6 miles) and take your pick between fresh Seafood from Mac’s on the Pier or enjoy a drink and some live music from the open air bar the Pearl.<br><br>If you are looking for a multi-building private home with two outdoor showers and room for the whole family, look no further than Pine Valley!<br><br>Home Details:<br>-Sleeps 8<br>-3 Floors<br>-2nd Floor Master Bedroom: 1 Queen Bed w/ en suite Full Bathroom & Jacuzzi Tub<br>-2nd Floor lofted area: 1 Twin Daybed<br>-Ground Floor Bedroom #2: 1 Queen Bed<br>-Ground Floor Bedroom #3: 2 Twin Bed<br>-Guest House Bedroom: 1 Queen Bed<br>-Main House: 2 Full Bathrooms & 1 Half Bathroom<br>-Guest House: 1 Full Bathroom<br>-Central AC via minisplit<br>-WiFi<br>-Smart TV<br>-Washer/Dryer<br>-Gas Grill <br>-Fire Pit (gas)<br>-Wrap Around Deck<br>-2 Outdoor Showers<br>-Screened Porch<br>-NO pets (fines remitted) <br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0418433180

13301 - The Oyster House: Classic Cape Great Location! Dog Welcome! Escape to the idyllic charm of Wellfleet with a stay at the delightful Oyster House—a cheerful haven offering the quintessential Cape Cod experience. With a brand new central AC system installed in 2025!<br><br>This inviting home provides the perfect base for your Wellfleet adventure. Enjoy leisurely strolls to downtown Wellfleet and Mayo Beach, where sun-drenched days await, filled with beach-combing, paddle boarding, and frolicking in the crystal-clear waters of the kettle ponds. Immerse yourself in nature as you explore the scenic trails of the Audubon, or meander along Main Street, soaking in the quaint charm of Wellfleet Harbor.<br><br>Experience the magic of Wellfleet’s "off-season" with visits to Oysterfest and Holly Folly, or simply savor the serene beauty of Fall and Winter on the Cape. When hunger strikes, indulge in delectable dining options at local favorites like Mac’s Shack, The Pearl, and PJ’s Family Restaurant.<br><br>Back at the Oyster House, unwind in comfort with modern amenities including central AC, TV, complimentary sheets and towels, and WiFi. Whether you’re seeking sunny summer adventures or cozy winter retreats, create cherished memories that will last a lifetime at the Oyster House—a true gem on the Cape.<br><br>Please note the main entry door is a up a set of steps, however, you can use the patio door in the back if you would like to avoid steps to enter and exit once you have entered and unlocked the home through the main entry door. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 4<br>-Single floor<br>Bedrooms<br>-Total 2<br>-1st Floor Bedroom: 1 Queen bed<br>-1st Floor Bedroom: 2 Twin beds<br>Bathrooms<br>-Total 1<br>-1st Floor: Full Bathroom w/ Shower/Tub combo<br>Other Amenities<br>-Central AC<br>-TV<br>-WiFi<br>-Washer and dryer<br>-Private yard with deck and patio<br>-Gas grill<br>-Outdoor shower<br>-Fireplace NOT for guest use (fines remitted)<br>-please note outdoor amenities are seasonal<br>-15 minute walk to the water and downtown<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for a maximum of 2 cars<br>-C0416383180

13341 - The Wellfleeter: Steps to water, easy access to town center! The waves crash on shore and the sand sifts between your toes, just steps from your front door at the Wellfleeter. <br><br>Two separated suites provide privacy and comfort with this home’s unique layout, the perfect solution for relaxation on your next vacation. The upstairs unit has vaulted ceilings, with exposed wood beams towering over the open concept living room and kitchen. A nice dining table separates the kitchen and living room, a great spot for morning coffee or an evening meal. Just off of the kitchen is a bedroom with two twin beds, and access to the Jack and Jill bathroom with shower tub combo and make up station. Off of the living room, the second bedroom houses a queen size bed with additional access to the bathroom. The ground level suite is a lovely space for additional privacy on your vacation. Accessed via the exterior door at the front of the home, the private entrance opens into the shared bedroom and seating area, with king size bed and stylish decor across from the cozy tv space. At the rear of the suite, a full bathroom with shower and laundry room can be found. <br><br>Outdoors, there is no shortage of options to choose from to enjoy the salt air. A set of benches and a table at one end of the deck provide space to sit and chat, while a picnic table at the other end of the deck offers seating for six if you’d like to dine al fresco. Perched at the East end of Mayo Beach, the location of the Wellfleeter can’t be beat! You can even avoid any crowds and relax on the complex’s private association beach, or take a quick stroll into Wellfleet’s beautiful downtown, with restaurants and shops for your vacation fun. Spend your next vacation in comfort and style, at the Wellfleeter!<br><br>Please note: there is no interior access between suites (i.e. you need to go outside to access the 1st floor from the deck entrance and ground floor from the front of the home)<br><br>Home Details<br>-No Pets (fines remitted)<br>-722 sq. ft.<br>Bedrooms<br>-Total 3<br>-Ground Floor Bedroom: 1 King Bed w/ En Suite Bathroom<br>-1st Floor Bedroom: 1 Queen Bed w/ en suite Jack and Jill Bathroom<br>-1st Floor Bedroom: 2 Twin Beds w/ en suite Jack and Jill Bathroom<br>Bathrooms<br>-Total 2<br>-Ground Floor: Full Bathroom w/ Shower (en suite King Bedroom)<br>-1st Floor: Full Bathroom with Tub/Shower Combo (Jack and Jill style en suite Queen Bedroom and Twins Bedroom)<br>Other Amenities<br>-Floor A/C Units<br>-TV with Apple TV<br>-Smart Lock/ Self Check-In<br>-WiFi<br>-Washer and Dryer (Ground Level)<br>-Deck with Outdoor Dining<br>-Charcoal Grill (Bring your own charcoal)<br>-NO PETS (Fines remitted)<br>-Access to Private Association Beach<br>-Walk to Mayo Beach<br>-Walk to Restaurants and Wellfleet Town Pier<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0410903180

12218 - Spring Bluff: Views of Bay Access to Private Beach! Set atop a hill in Truro overlooking Cape Cod Bay, welcome to Spring Bluff! A walk up a flight of exterior stairs brings you to the home’’s entrance. Once inside, cook up a meal in the full kitchen and enjoy it in the cozy dining area. Watch a movie in the living room before heading to bed in one of two bedrooms in this sleeps 4 home. A set of twin beds in one bedroom and a queen bed in the other are the perfect places to count sheep after a day on the beach. <br>Boasting one of the most iconic views of the Cape, stare straight across Cape Cod Bay to the tip of Provincetown, with Pilgrim Monument clearly defined in the near distance. The breathtaking view is only one of the many perks of staying here. A private bayside beach is a short walk down a path at the edge of the property, while the shuttle to Provincetown center allows the opportunity to leave your vehicle parked at home for a carefree and car-less day. <br> <br>Spring Bluff is one of five two-bedroom cottages available for rent at this property; other cottages include Sunset Bluff (12215), Wind Bluff (12216), Bay Bluff (12217) and Summer Bluff (12219). <br> <br>Home Details: <br>-Sleeps 4 <br>-Single Floor <br>-2 Bedrooms <br>-Bedroom #1: 1 Queen Bed <br>-Bedroom #2: 2 Twin Beds <br>-1 Bathroom <br>-Bathroom #1- Full Bathroom with Shower <br>-AC via mini-split (please note, there is one AC unit that can cool the whole home, but you will need to leave the interior doors open) <br>-TV with Cable <br>-WIFI <br>-Smart Lock/ Self Check-In <br>-Deck with Outdoor Dining <br>-Propane Grill <br>-NO PETS (fines remitted) <br>-Waterfront <br>-Walk to Private Beach <br>-Walk to Shuttle Stop for Provincetown Center <br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival <br>-Cleaned with Hospital Grade Disinfectant<br>C0425763000

12219 - Summer Bluff: Beautiful Views of Cape Cod Bay! Set atop a hill in Truro overlooking Cape Cod Bay, welcome to Summer Bluff! <br><br>A walk up a flight of exterior stairs brings you to the home’’s entrance. Once inside, cook up a meal in the full kitchen and enjoy it in the cozy dining area. Watch a movie in the living room before heading to bed in one of two bedrooms in this sleeps 4 home. A set of twin beds in one bedroom and a queen bed in the other are the perfect places to count sheep after a day on the beach.<br><br>Boasting one of the most iconic views of the Cape, stare straight across Cape Cod Bay to the tip of Provincetown, with Pilgrim Monument clearly defined in the near distance. The breathtaking view is only one of the many perks of staying here. A private bayside beach is a short walk down a path at the edge of the property, while the shuttle to Provincetown center allows the opportunity to leave your vehicle parked at home for a carefree and car-less day.<br><br>Summer Bluff is one of five two-bedroom cottages available for rent at this property; other cottages include Sunset Bluff (12215), Wind Bluff (12216), Bay Bluff (12217), and Spring Bluff (12218).<br><br>Home Details:<br>-Sleeps 4<br>-Single Floor<br>-2 Bedrooms<br>-Bedroom #1: 1 Queen Bed<br>-Bedroom #2: 2 Twin Beds<br>-1 Bathroom<br>-Bathroom #1- Full Bathroom with Shower<br>-AC via mini-split (please note, there is one AC unit that can cool the whole home, but you will need to leave the interior doors open) -Heating- mini-split system<br>-TV with Cable<br>-WIFI<br>-Smart Lock/ Self Check-In<br>-Deck with Outdoor Dining<br>-Propane Grill<br>-NO PETS (fines remitted)<br>-Waterfront<br>-Walk to Private Beach<br>-Walk to Shuttle Stop for Provincetown Center<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0425773000

13379 - The Osprey Nest: Spacious 4 Bedroom with AC, Dog Friendly! Discover the serene beauty of Cape Cod at this unique home in Wellfleet. This enchanting four-bedroom, two and a half-bathroom retreat promises a blend of comfort and adventure, accommodating up to eight guests. Just a short drive away, Mayo Beach awaits with calm harbor waters, while Marconi Beach offers sweeping Atlantic views. A quick 12 minute drive will bring you to the renowned Wellfleet Beachcomber and Cahoon Hollow Beach. <br><br>Inside, the spacious kitchen flows seamlessly into the inviting dining area, perfect for gatherings and lively dinners. The smart TV and ping pong table in the game room promise fun-filled evenings, while split and floor unit air-conditioning ensures your comfort.<br><br>Outside, the expansive back deck—set amidst the whispering woods—offers a tranquil space for morning coffee or sunset reflections. An outdoor shower adds a touch of convenience after beach excursions.<br><br>Explore the nearby Great Island Trail, just a ten-minute drive away. For a taste of local flavors, head 7 minutes to downtown Wellfleet, try the iconic Moby Dick’s Restaurant and other eateries!<br><br>Whether you’re unwinding in the secluded garden or embarking on coastal adventures, this Wellfleet home is your gateway to Cape Cod’s wonders. Secure your stay today, and let the magic of the Cape embrace you.<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 King Bed<br>-1st Floor Bedroom: 2 Twin Beds<br>-1st Floor Bedroom: 1 Queen Bed<br>-Ground Floor Bedroom: 1 Queen Bed<br>Bathrooms<br>-Total 2.5<br>-1st Floor: Full bath, shower/tub combo<br>-1st Floor: Full bath, shower/tub combo (ensuite)<br>-Basement/Ground floor: ½ bathroom<br>Other Amenities <br>-Split System AC and floor Unit ACs<br>-WiFi<br>-Smart TV<br>-Streaming Service<br>-Washer/Dryer <br>-Ping Pong Table<br>-Propane Grill <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>-C0546083180

12215 - Sunset Bluff: Views of the Bay Private Beach Access! Set atop a hill in Truro overlooking Cape Cod Bay, enjoy Sunset Bluff! <br> <br> A walk up a flight of exterior stairs brings you to the home’s entrance. Once inside, cook up a meal in the full kitchen and enjoy it in the cozy dining area. Watch a movie in the living room before heading to bed in one of two bedrooms in this sleeps 4 home. A set of twin beds in one bedroom and a queen bed in the other are the perfect places to count sheep after a day on the beach.<br> <br>Boasting one of the most iconic views of the Cape, stare straight across Cape Cod Bay to the tip of Provincetown, with Pilgrim Monument clearly defined in the near distance. The breathtaking view is only one of the many perks of staying here. A private bayside beach is a short walk down a path at the edge of the property, while the shuttle to Provincetown center allows the opportunity to leave your vehicle parked at home for a carefree and car-less day. <br><br>Sunset Bluff is one of five two-bedroom cottages available for rent at this property; other cottages include Wind Bluff (12216), Bay Bluff (12217), Spring Bluff (12218) and Summer Bluff (12219). <br><br>Home Details:<br>-Sleeps 4<br>-Single Floor (must go up a flight of steps to enter home)<br>Bedrooms<br>-Total 2<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 2 Twin Beds<br>Bathroom<br>-Total 1<br>-1st Floor: Full Bathroom w /Shower<br>Other Amenities<br>-AC via mini-split (please note, there is one AC unit that can cool the whole home, but you will need to leave the interior doors open) -TV<br>-WIFI<br>-Smart Lock/ Self Check-In<br>-Deck with Outdoor Dining<br>-Propane Grill<br>-Waterfront<br>-NO PETS (fines remitted)<br>-Walk to Private Beach<br>-Walk to Shuttle Stop for Provincetown Center<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0425783000

13319 - The Sandbox: Family Compound walk to Downtown! When going on vacation, you want to bring the whole family with as many friends as possible. With three separate dwellings sleeping 14 folks, don’t leave anyone behind this trip. It’s time to play in The Sandbox! Upon arriving at this stunning compound, your first decision is which building to explore. New for 2023, each building has a mini-split AC system to keep everyone cool and comfortable. Entering the main house, you walk into the home’s beautiful kitchen, complete with center island with breakfast bar, plenty of counter space, and built-in dining nook. Passing under the arched brick doorway, your jaw will drop when you enter the incredible centerpiece of the main house: the great room that combines a formal dining room, living room, and game room under its exposed wood beams and vaulted ceilings. <br><br>Upstairs, the main home’s sleeping arrangements can be found, with three separate bedrooms to choose from. Two of the three bedrooms house comfortable queen size beds, while the final bedroom is perfect for the kiddos to crash with the twin bunk bed and fun colors adorning the walls. <br><br>Just off of the main house, a breathtaking guest studio is a great space to gain a little extra privacy on your vacation, while sacrificing absolutely none of the luxury. With towering ceilings, this studio feels like anything but the typical New York studio apartments you may picture upon hearing “guest studio.” A full kitchen means you can even cook in privacy and comfort, while natural light floods in from skylights, the large glass doors and windows throughout. Finally, a queen size bed awaits your night of slumber. <br><br>Last and not certainly not least, a final guest house completes the dwellings on this family compound. Giving the rustic Cape Cod experience, this guest house has three bedrooms and one bathroom. <br><br>The outdoors of this property are sure to be utilized throughout the vacation. The main home has a screened in porch and patio with outdoor dining options, perfect for a summer night meal. Or, enjoy yard games and have ample space for your four-legged friend to run around, all while enjoying the privacy Wellfleet brings. <br><br>Other amenities include a washer and dryer (located in the main house), and a charcoal grill. Don’t leave anyone behind on your next vacation, pup included, it’s time to live like a kid again and go play at the Sandbox!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 14<br>-3 Dwelling Compound (Main House, Guest Studio, Guest House)<br>-Mini-Split AC System<br>-Main House: 2 Floors (1st Floor + 2nd Floor)<br>-Guest Studio: Single Floor<br>-Guest House: Single Floor<br>7 Bedrooms Total<br>-Main House<br>-Bedroom #1: 1 Queen Bed, 2nd floor<br>-Bedroom #2: 1 Queen Bed, 2nd floor<br>-Bedroom #3: 1 Twin Bunk Bed, w/twin trundle, 2nd floor<br>-Guest Studio<br>-Bedroom #4: 1 Queen Bed<br>-Guest House<br>-Bedroom #5: 2 Twin Beds<br>-Bedroom #6: 1 Twin Bed<br>-Bedroom #7: 1 Queen Bed<br>5 Bathrooms Total<br>-Main House <br>-Bathroom #1: Full Bathroom with Shower, 1st Floor<br>-Bathroom #2: Full Bathroom with Shower, 1st Floor<br>-Bathroom #3: Full Bathroom with Shower, 2nd Floor<br>-Guest Studio<br>-Bathroom #4: Full Bathroom with Shower<br>-Guest House<br>-Bathroom # 5: Full Bathroom with Tub/ Shower Combo<br>-Smart TV with Streaming<br>-Washer and Dryer (Main House)<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Ping Pong Table<br>-Private Yard<br>-Charcoal Grill<br>-Quick Walk into Wellfleet Village and Town Pier<br>-5 Minute Drive to Ocean Beaches<br>-2 Minute Drive to Long Pond<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0402243180

12216 - Wind Bluff: Views of Bay Access to Private Beach! Set atop a hill in Truro overlooking Cape Cod Bay, enjoy Wind Bluff! <br> <br> A walk up a flight of exterior stairs brings you to the home’’s entrance. Once inside, cook up a meal in the full kitchen and enjoy it in the cozy dining area. Watch a movie in the living room before heading to bed in one of two bedrooms in this sleeps 4 home. A set of twin beds in one bedroom and a queen bed in the other are the perfect places to count sheep after a day on the beach.<br><br>Boasting one of the most iconic views of the Cape, stare straight across Cape Cod Bay to the tip of Provincetown, with Pilgrim Monument clearly defined in the near distance. The breathtaking view is only one of the many perks of staying here. A private bayside beach is a short walk down a path at the edge of the property, while the shuttle to Provincetown center allows the opportunity to leave your vehicle parked at home for a carefree and car-less day. <br> <br>Wind Bluff is one of five two-bedroom cottages available for rent at this property; other cottages include Sunset Bluff (12215), Bay Bluff (12217), Spring Bluff (12218) and Summer Bluff (12219). <br> <br>Home Details:<br>-Sleeps 4<br>-Single Floor<br>-2 Bedrooms<br>-Bedroom #1: 1 Queen Bed<br>-Bedroom #2: 2 Twin Beds<br>-1 Bathroom<br>-Bathroom #1- Full Bathroom with Shower<br>-AC via mini-split (please note, there is one AC unit that can cool the whole home, but you will need to leave the interior doors open) -Smart TV <br>-WIFI<br>-Smart Lock/ Self Check-In<br>-Deck with Outdoor Dining<br>-Propane Grill<br>-NO PETS (fines remitted)<br>-Waterfront<br>-Walk to Private Beach<br>-Walk to Shuttle Stop for Provincetown Center<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0425743000

12217 - Bay Bluff: Views of the Bay Access to Private Beach! Set atop a hill in Truro overlooking Cape Cod Bay, welcome to Bay Bluff! <br> <br> A walk up a flight of exterior stairs brings you to the home’’s entrance. Once inside, cook up a meal in the full kitchen and enjoy it in the cozy dining area. Watch a movie in the living room before heading to bed in one of two bedrooms in this sleeps 4 home. A set of twin beds in one bedroom and a queen bed in the other are the perfect places to count sheep after a day on the beach.<br> <br>Boasting one of the most iconic views of the Cape, stare straight across Cape Cod Bay to the tip of Provincetown, with Pilgrim Monument clearly defined in the near distance. The breathtaking view is only one of the many perks of staying here. A private bayside beach is a short walk down a path at the edge of the property, while the shuttle to Provincetown center allows the opportunity to leave your vehicle parked at home for a carefree and car-less day. <br><br>Bay Bluff is one of five two-bedroom cottages available for rent at this property; other cottages include Sunset Bluff (12215), Wind Bluff (12216), Spring Bluff (12218) and Summer Bluff (12219). <br> <br>Home Details:<br>-Sleeps 4<br>-Single Floor<br>-NO PETS (fines remitted)<br>Bedrooms<br>-Total 2 <br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total 1<br>-1st Floor: Full Bathroom w/ Shower -AC via mini-split (please note, there is one AC unit that can cool the whole home, but you will need to leave the interior doors open) <br>-TV with Cable<br>-WIFI<br>-Smart Lock/ Self Check-In<br>-Deck with Outdoor Dining<br>-Propane Grill<br>-Waterfront<br>-Walk to Private Beach<br>-Walk to Shuttle Stop for Provincetown Center<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0425753000

This property is professionally managed by Pretty Picky Properties Luxurious Estate by the Bay in Brewster: Sleeps 20 with Expansive New Pool, Walk to Beach, Walk to Town Rents Saturday to Saturday in Peak Summer Off-Season Weekends and Partial Weeks Available Choose this vacation headquarters and give your group of up to 20 the best of all options. A main house plus separate guest house on nearly an acre and a half of level yard for play space. A stunning new 20’ X 60’ heated saltwater pool with large stone patio. A three-minute walk to Brewster’s Breakwater Beach. And an eight-minute walk to the iconic Brewster Store and Main Street/Route 6A, where you’ll discover some excellent restaurant choices. The main house, just completed in 2020, offers elegance without pretense, centered on its spacious, thoughtfully outfitted chef’s kitchen. Here you’ll appreciate the large center island with high boy seating, beautiful granite and tile, as well as abundant counter space bathed in natural light. The kitchen opens to a TV lounge, which walks out to the expansive patio and pool. There is also a good-sized dining room here, as well as a handy half bath and laundry. The main house has sleeping for up to 12 in five bedrooms, two of which are king masters, one on the main level, the other upstairs. Each master has its own private full bath en suite. The separate guest house offers single level living and sleeps up to eight in three bedrooms with a full bath. You have a full eat-in kitchen here, as well as a TV lounge. Your outdoor summer living is optimized on the oversized patio which envelops the big pool. There’s also a hot tub, a large gas grill, a fire pit and an enclosed outdoor shower. Each house is centrally air conditioned, has cable TV, a SONOS Sound system and high speed Wi-Fi. 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 this site for more Pretty Picky Properties - 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 $245.00. 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 property is professionally managed by Pretty Picky Properties Alluring Chatham in-town home with pool, walk to it all Sleeps 10 Rents Friday to Friday during peak season Linens included, beds made Pool & Hot Tub open from Memorial Day to Columbus Day Here you’re close to everything that counts in Chatham. Walk 0.4 mile (8 minutes) to popular Oyster Pond Beach. Walk five minutes to the unique shops, restaurants and galleries of Main Street. You can order amazing take-out sushi from Blue Fins and be home with it before the edamame cools off! Consider your outdoor living options at this property. When you’re not splashing with the kids in the large, heated in-ground pool, you’ll be lounging in the shade of several large poolside umbrellas. Or serving appetizers and drinks on the superb screened porch, cooled by a perfectly placed ceiling fan. Maybe you’ll fire up the gas grill, after rinsing off the beach sand and salt in the outdoor shower. Or jump in the hot tub and enjoy the starry evening. It’s amazing how much privacy you have in these outdoor spaces, given your location in the heart of Chatham. Inside, this home provides 2,800 square feet of the most upscale, yet unpretentious accommodations you could ever hope for in a summer vacation home. The well-outfitted chef’s kitchen is big and bright with custom cabinets, stainless steel and granite throughout. There’s highboy seating at the large center island, encouraging a pleasantly social meal prep experience. The kitchen flows into the elegant dining room, embraced by two walls almost entirely comprised of oversized windows, adding to the cheery ambience. The dining area, in turn, flows into the living room and TV lounge with its comfy seating and large flat screen smart TV. There’s one bedroom on the main level. It’s roomy with a generous king size bed. You’ll find a full bath with a combination tub/shower directly across the hall. The rest of the main level is allocated to a mud room back entry, laundry and a second stairway that leads up to a huge primary bedroom over the garage. The primary has a king size bed plus a twin bed with trundle underneath. There’s a luxurious full bath en suite, offering a twin sink vanity and step-in shower. Another second level bedroom has a queen size bed plus a twin with trundle. Down the hall you’ll find a bedroom with two twins, each with a trundle. There is also a loft at the top of the main stairway which features a desk, for those zoom calls, and a queen size sleep sofa. For those days when the weather doesn’t cooperate there is a wonderful game room for kids of all ages in the lower level. Down there you’ll find a foosball table, air hockey, a pop-a-shot hoops game plus comfy seating and a large flat screen TV! There’s even a table for playing cards or board games. Overall the home has four bedrooms and three full baths. It sleeps up to 10. It has central air conditioning, high speed Wi-Fi and cable/smart TVs. 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%. This property offers a three-night minimum stay during select weeks in May – June & 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! ® Town of Chatham Registration #151

This property is professionally managed by Pretty Picky Properties Luxurious Chatham Home with Expansive Water Views Sleeps 10 in 4 bedrooms, 4.5 baths Rents Friday to Friday during peak season Linens included, beds made Location Water views from almost every room! Walk to two beaches and a shared dock! Located in one of Chatham’s most picturesque neighborhoods, this newly renovated and expanded residence has undergone an amazing transformation that now highlights stunning water views of saltwater Crow’s Pond. Indoor Space Upon entry, you are greeted by an impressive foyer that welcomes you to both the common and private areas of this nearly 4,000 square foot home. Built in 1985 and remodeled in 2023, the open floor plan of this 4-bedroom home is enhanced by gorgeous white oak flooring and professional interior design. The home features a state-of-the-art kitchen with top-of-the-line custom cabinetry, Thermador® appliances, weathered Quartzite® countertops, and custom tile work. A pillar flanked sunroom with skylights and bank of windows perfectly frames westerly views of the water. The living room is adjacent and features more cozy seating with a TV over the fireplace. There’s also a spacious office on the first floor. The main level also presents a laundry room with two washers and two dryers, a powder room, and a California Closet® pantry. The lower level provides a bright family room with custom built-ins, wet bar and billiard table. Outdoor Space Professionally landscaped, the home features an artistic blend of brick walkways, natural stone steps, and native plantings. The home has an enclosed outdoor shower and has easy access to a shared deep-water dock across the street, as well as to two private beaches on Pleasant Bay (8-minute walk) and on Crow’s Pond (across the street). Sleeping Accommodations On the main level you’ll find one of two primary suites with a four poster King bed, offering captivating water views and a spa-like bathroom with high-end fixtures. On the second level there is an additional King bed primary suite showcasing glass sliders leading to a private balcony with wonderful water views. You’ll be delighted by the luxurious, private bathroom with soaking tub and double vanity. The primary suite also has two walk-in closets. Additionally on the second level, another loft area greets you at the landing with views of Crow’s Pond. There is a second bedroom up here with a King bed and an exceptionally appointed full bathroom. There is also a bedroom on the lower level with two twin-over-full bunk beds. There is a full bathroom on this level as well. 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%. 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! ® Town of Chatham Registration #956

13358 - Flip-Flops & Treetops: Short Walk to Long Pond Swimming Beach! Grab your sandals, the serenity of the National Seashore is calling your name. It’s time to get lost in the peacefulness of the woods of Wellfleet; it’s time to come to Flip-Flops & Treetops.<br><br>A sunshine yellow door welcomes you into this incredible home nestled in the woods of Wellfleet. Stepping inside, a spacious dine-in kitchen welcomes you in, complete with dining table and brick chimney anchoring the room. Past the chimney, a sun-soaked seating area with colorful knick-knacks and fun chandelier is a great spot to play board games or catch up with your fellow vacationers. Stepping through the sliding glass doors, a back patio sits behind the home, ready for vacation meals and bedtime drinks. <br><br>Back inside, fun and entertainment awaits in the home’s sprawling living room, located on the left side of the home. The sectional welcomes you in for movie night, grab a meal at the dining table, or access the backyard through patio doors at the rear of the room. <br><br>You’ll have plenty of sleeping options to choose from with six bedrooms, sleeping ten vacationers in this single story home. Walk down the long hallway on the right of the home where the sleeping quarters can be found. The primary bedroom has a king size bed and its own private access to the backyard through two separate sliding glass doors. There is another bedroom with a king size bed, two of the remaining bedrooms have two twin beds in each room, while the final two bedrooms have a single twin bed. The whole home is cooled through a mini-split AC system; only one bedroom has a mini-split in the bedroom. <br><br>Located adjacent to the National Seashore, your home is perfectly situated for beach fun. Avoid any traffic with a short drive on the back roads to downtown Wellfleet and Wellfleet Harbor, two must see gems of the Outer Cape. <br><br>Other amenities include a washer and dryer, ping pong table and an outdoor shower. This architectural gem is both an incredible homebase for your Cape Cod exploration, and an even better space to relax in after a long day vacationing. Experience the wonders of Wellfleet at Flip-Flops & Treetops. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 10<br>-Single Floor<br>Bedrooms<br>-Total 6<br>-Bedroom #1: 1 King Bed<br>-Bedroom #2: 1 King Bed<br>-Bedroom #3: 2 Twin Beds<br>-Bedroom #4: 2 Twin Beds<br>-Bedroom #5: 1 Twin Bed<br>-Bedroom #6: 1 Twin Bed<br>Bathrooms<br>-Total 2<br>-Bathroom #1: Full Bath w/ Shower<br>-Bathroom #2: Full Bath w/ Shower<br>-Fully Equipped Kitchen<br>-Mini-Split A/C Units<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV/Streaming<br>-Board Games<br>-Washer/Dryer (basement)<br>-Ping Pong Table<br>-Patio w/ Outdoor Dining<br>-Propane Grill<br>-Outdoor Shower<br>-Abutting National Seashore<br>-7 Min Walk (0.3 mile) to Long Pond Swimming Beach<br>-0.6 Mile to Downtown Wellfleet<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0413163180

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 $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 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 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 $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! ®

This property is professionally managed by Pretty Picky Properties Sleeps 16 Eight Bedrooms, Nine Baths Rents Friday to Friday during Peak Season Linens Included, beds made Pool is open from Memorial Day through Columbus Day weekend This totally renovated former Bed & Breakfast, known as the Chatham Gables Inn, brings a new level of luxury and comfort to a Chatham vacation for your group of up to 16. Not that you will ever feel the need to leave the property, but should you choose to venture out, it’s good to know you’re close to everything you love about Chatham. Bring or rent bikes! That’s all you’ll need with so much, so close. Bike five minutes to Lighthouse Beach, Chatham’s biggest and best. Or ride two minutes to Oyster Pond Beach (aka Children’s Beach), a smaller, more sheltered beach. Or walk down to the Chatham Pier Fish Market, where you can take home the catch of the day, fresh off the boat. And it’s only a few-minutes’ walk to Main Street, Chatham Village, for shops, restaurants, galleries, concerts, Cape League baseball, playground, tennis courts, ice cream parlors and much more. The 4,200+ square foot house presents the perfect intersection of classic New England charm and leading-edge creature comforts and convenience. Exposed beam ceilings, heated wide plank wood floors and tasteful choices of furnishings, fabrics, paint and wallpaper all combine to create a one-of-a-kind living experience. The home’s centerpiece is the gleaming white farmhouse kitchen with its expansive center island with second sink. All appliances are new and commercial grade. The kitchen flows into the charming conservatory, which in turn, opens to the patio beyond. Your outdoor living will, of course, center on the beautiful, heated pool and adjacent hot tub. There is also a gas fueled fire pit, so your outdoor pleasure extends beyond sunset. The gas grill lives out here, as well, and you’re likely to prepare and serve most meals using the outdoor kitchen-area and patio dining table and chairs. This home offers multiple inviting lounge areas, each as comfortable and appealing as the next. Sleeping accommodations include eight bedrooms, each with its own name such as “Surfside,” “Nantucket” or “Great Point.’ Each has bedding for two. There are five kings, one queen and two bedrooms each with two twins. Each bedroom has its own private full bath en suite, and each has a smart TV. The lower level includes an oversized laundry with two washers and two dryers plus an additional refrigerator. And to complete its resort-like amenities, there is a game room down here as well. There is cable/smart TV and high-speed Wi-Fi, of course. The home is cooled via an ultra quiet system, which allows customized climate control for each bedroom. It also features Lutron Lighting® allowing guests to automatically or manually adjust the level and even the color of the LED light to create the ideal environment for any living space. 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%. 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! ® Town of Chatham Registration #152