Vacation rentals in Pleasant Bay

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Top-rated vacation rentals in Pleasant Bay

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Top guest favorite

An aerial view captures a cottage nestled among vibrant green trees, showcasing the surrounding natural landscape. A glimpse of the ocean is visible in the distance. The cottage features a deck facing the woods, providing a serene and secluded ambiance.

Home in Orleans

Peaceful Nauset Beach Sanctuary

Imagine driving down a quiet private dirt road behind one of the nicest beaches on Cape Cod. Enter the property through a gate and walkway and you’re in your own private sanctuary. The cottage feels like a treehouse looking onto the tidal marsh behind Nauset Beach. Inside you will feel the vibes of a nostalgic cape cod cottage with modern amenities and style. Chill out on the deck. Take a 10 minute walk to a private section of Nauset Beach or drive to our free association Nauset parking lot.

5.0 out of 5 average rating, 35 reviews

Guest favorite

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

Home in Chatham

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

4.95 out of 5 average rating, 320 reviews

Top guest favorite

A charming cottage with a shingle exterior is framed by a vibrant yard. A white picket fence encloses flower beds, and a small patio features an umbrella for shade. A welcoming pathway leads to the front door, surrounded by greenery and a manicured lawn.

Cottage in Chatham

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property

4.97 out of 5 average rating, 295 reviews

Top guest favorite

A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.

Guest suite in Harwich

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Eleven year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

4.99 out of 5 average rating, 665 reviews

Top guest favorite

A charming single-story home is presented with light grey shingles and dark blue shutters. A paved pathway leads to the front door, framed by manicured green lawns and landscaped flower beds. Trees and shrubs add to the serene outdoor environment.

Cottage in Harwich Port

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

4.95 out of 5 average rating, 429 reviews

Top guest favorite

A rustic, two-story cabin is surrounded by lush landscaping. A green door welcomes visitors, while a small stone pathway leads to a pair of outdoor chairs situated on a grassy lawn. The harmonious design includes natural stone walls and shaded trees.

Apartment in Chatham

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

4.96 out of 5 average rating, 307 reviews

Top guest favorite

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

4.98 out of 5 average rating, 131 reviews

Top guest favorite

A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

Home in Chatham

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

4.97 out of 5 average rating, 174 reviews

Top guest favorite

Home in Brewster

4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC

Relax at this spacious mid-Cape retreat on a quiet private road, just a 5-minute walk to a private swimming beach and pond. Canoe included! Sleeps 8 with 4 bedrooms (2 on the main level, 2 upstairs) and 3 full baths with bidets. Enjoy central A/C, hardwood floors, a screened porch, 65" OLED TV, gas stove, gas fire table and grill, ping pong, and wooded yard. Convenient main-level washer/dryer. Near the Cape Cod Rail Trail, beaches, golf, tennis, boating.

4.93 out of 5 average rating, 163 reviews

Guest favorite

A charming exterior of the Carriage House features weathered shingle siding and a cupola on the roof. Surrounded by landscaped gardens, the entrance showcases a well-kept pathway and a mix of greenery and blooming flowers, creating a welcoming ambiance.

Home in Eastham

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.

4.96 out of 5 average rating, 206 reviews

Top guest favorite

A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.

Home in Chatham

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

5.0 out of 5 average rating, 29 reviews

Guest favorite

An outdoor gathering area is arranged around a circular fire pit, with several comfortable chairs and accent tables. The surrounding garden is filled with lush greenery and vibrant blue hydrangeas. Soft lighting enhances the cozy ambiance as twilight descends.

Home in Orleans

Walk to Lake + Fire Pit | Near Nauset + Sleeps 10

Let the Cape Cod breeze clear your thoughts and the sound of birdsong reset your pace. This beautifully renovated Orleans retreat sits on a quiet wooded lot — walk 5 minutes to Pilgrim Lake, stroll through the woods to Arey's Pond, or drive 7 minutes to Nauset Beach. Three bedrooms sleep up to 10, with a designer coffee bar, firepit, grill station, and game room waiting for you. There is a lot to donor nothing at all.

4.99 out of 5 average rating, 111 reviews