Vacation rentals in Little Pleasant Bay

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Top-rated vacation rentals in Little Pleasant Bay

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Guest favorite
Guest suite in Orleans
4.9 out of 5 average rating, 222 reviews

Charming Old Cape Cod

Indulge in relaxation and leisure at Snowtop on the Town Cove. The charming retreat features a private entrance, a spacious bedroom with a king size bed, a full bath, and a sunlit living room with a dining table overlooking picturesque Town Cove. The view in the photo is your front yard. Guests often enjoy sitting outside to watch boats drift by and the sky change color to a sunset. Nestled on a quiet road, Snowtop is 3 miles from beautiful Nauset Beach and 2 miles from the center of Orleans.

Guest favorite
Home in Harwich
4.92 out of 5 average rating, 26 reviews

7th Vacation in Harwich

Pleasant Lake Region of Harwich with deeded access to Long Pond and Cape Cod Rail Trail bike path. Newly renovated! Bright and Spacious! Sky-lighted modern kitchen, Master bedroom suite. Large deck with benches overlooking the backyard. Central heat & A/C. Hardwood floors. Game room with a foosball. A study area. Washer and dryer included. Outdoor shower. A fire pit and 5 car parking on a driveway on a corner lot make entertaining family and friends welcome! Let your Cape Cod adventure starts!

Guest favorite
Home in Harwich
4.94 out of 5 average rating, 49 reviews

Relaxing Harwich retreat with beautiful back yard

Welcome to Cape Cod! Surrounded by golf courses, Pleasant Bay beaches, and scenic shaded trails, this spacious and well-built ranch is located on a quiet dead-end street and within walking distance of Wequassett Resort and Golf Club - perfect for wedding guests and relaxing Cape getaways. The home features refinished hardwood floors, updated bathrooms, and a large deck, a newly renovated designed backyard. Enjoy complimentary bicycles and beach essentials for the perfect Cape Cod experience.

Superhost
Home in Eastham
5 out of 5 average rating, 4 reviews

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

Top guest favorite
Guest suite in Chatham
4.99 out of 5 average rating, 132 reviews

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

Top guest favorite
Guest suite in Harwich
4.99 out of 5 average rating, 651 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten 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.

Top guest favorite
A sunlit living area features large glass windows offering views of the surrounding greenery and tranquil water. A round table is set for relaxation. A ceiling fan hangs above, while potted plants and a lounge chair complete the serene atmosphere.
Home in Dennis
4.98 out of 5 average rating, 49 reviews

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

18+ Lovely waterfront tranquil getaway. All nearby houses hidden! This gem of a spot has been curated to soothe the soul! The cottage is sitting on Bakers Pond with an unobstructed view surrounded by conservation land *The driveway abuts a road* Wildlife can be observed. Swim or fish in this very clean kettle pond! The edges of the pond require water shoes for comfort as this is a natural body of water with no man-made beach/interference of nature. Kayaks, and life jackets available

Superhost
A tranquil outdoor space features white lounge chairs positioned on a grassy area, overlooking Cape Cod Bay. Vibrant flowers in the foreground add color, while serene water views and tree foliage create a peaceful natural setting.
Cottage in Brewster
4.85 out of 5 average rating, 65 reviews

BeachFront Private Beach Amazing Views WIFI

Sunset Cottage, Amazing Location on a secluded bluff, with fantastic views of Cape Cod bay, Beach front! A/C WIFI Simple Cottage, natural setting, safe quiet clean Beautiful huge Private beach for 3 cottages and the main house. All photos are on the property Desirable Brewster MA on the Bay. Amazing sunset views over the ocean from every room. Full kitchen, large living room, Master Queen bedroom, 2nd queen bedroom (coolgel matress), Long wide private beach. 360 feet long!!

Guest favorite
An outdoor seating area features four wooden chairs arranged around a stone fire pit. Colorful accent tables are positioned beside the chairs. Surrounded by greenery, the space offers a natural setting, creating a tranquil atmosphere for relaxation and gatherings.
Apartment in Brewster
4.96 out of 5 average rating, 182 reviews

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

Superhost
Home in Harwich
5 out of 5 average rating, 4 reviews

Cape Cod Historical Oasis | Mecarta Farm

Step back in time with modern comforts at this enchanting mid-1800s Harwich home. Brimming with timeless New England charm, it features period details, cozy living spaces, and updated amenities. Outside, enjoy lush gardens and a spacious backyard ideal for relaxing or entertaining on warm summer nights. Just minutes from Harwich’s scenic beaches, local dining, and vibrant downtown, this home offers the perfect blend of history, comfort, and Cape Cod tranquility.

Guest favorite
Home in Orleans
4.93 out of 5 average rating, 27 reviews

Orleans, MA Luxury Getaway

Enjoy the best the Cape has to offer! Stay at this hidden gem in Orleans, MA. Easy access to Nauset Beach and Little Pleasant Bay. Large, luxurious, and family friendly with a big yard in a quiet neighborhood. Enjoy our gazebo, firepit, outdoor grill, outdoor patio dining, and outdoor shower. Inside, luxuriate in this 4 bed 4 bathroom with a modern kitchen, breakfast nook, dining room, and living room. Washer and dryer included in basement.

Top guest favorite
Home in Harwich
5 out of 5 average rating, 38 reviews

The Hideaway - Harwich Port Getaway

Your family will be close to everything Harwich Port has to offer when you stay at this centrally-locally oasis! Central Air! TV in everyroom! Large fully fenced in backyard for summer cookouts & fires! Come stay in our newly renovated home that has everything you will need. Only minutes from major beaches, shopping, restaurants and all of the beautiful things Cape Cod has to offer. *more outdoor photos to come soon!

Popular amenities for Little Pleasant Bay vacation rentals