Vacation rentals in Little Pleasant Bay

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.

Joy Cottage: a/c, EV charger, outdoor shower

Welcome to Joy Cottage! Our Cozy Cape Cod cottage is tucked away in the woods, within walking distance to Bakers Pond in Orleans, MA, Nickerson State Park, 4.5 miles from Nauset Beach, 2 miles from Skaket Beach and minutes to Main St. Orleans. Features: EV charger, large deck, roomy outdoor shower, private backyard, full kitchen, dining area, two wall mounted AC units, private laundry, beach supplies. Please be advised that there is a spiral staircase which might not be suitable for some guests.

Luxury Home- Chatham Center- Walk to Town + Beach

Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is perfect for families, couples, or a group of friends looking to be walking distance to restaurants, boutiques, the beach & so much more! Enjoy an extremely spacious home with almost 2,700 sq ft of living space, 3 ensuites, & a large roof deck. In Downtown Chatham .3 Miles to Oyster Pond .5 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

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!

Cozy beachside apartment

Only an hour away from Boston, making it easy to plan your visit. Only a 5 minute walk to beautiful Sagamore beach, and easy hopping point if you’d like to go further down Cape Cod. 25 minutes from both Hyannis and Woods Hole to hop on the ferries to Nantucket / Martha’s Vineyard. 5 minute drive to the nearest grocery store and 20 minutes from two hospitals. Feel free to make use of both of my paddle boards or my tandem, two-person kayak, which stays down at the beach in the summer for you!

Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!

Discover Sweetbriar, a 1940s two-bedroom 600 sqft Cape Cod retreat in Eastham’s peaceful Cottage Grove. Minutes from First Encounter Beach and Fort Hill, this cozy, dog-friendly cottage blends classic charm with modern comfort. Relax on the private deck, explore scenic bike trails, and unwind in a warm, inviting space. With easy access to beaches, villages, and nature, Sweetbriar offers the perfect escape for unforgettable Cape Cod days. Book now and experience the magic of the Cape!

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!!

Cape Cod Cottage by the Bay!

Classic, beautifully crafted, newer cottage by Cape Cod Bay. All amenities. Stainless steel kitchen, Cathedral ceilings, Wide plank wood floors, water view. 2 min walk to one of the best beaches on the Cape! Quiet locale in the historic village of Quivet Neck, within East Dennis. 35 miles to Provincetown. I do not allow pets. I have family members with severe allergies who use the cottage. There is no AC at this cottage. I have 15 windows, 4 fans and an ocean breeze.

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.

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Nauset Nook

Relax and kick your feet up. Enjoy nature from your own deck (abutting wooded conservation land). Spacious and centrally-located. Only 2.5 mi. to Nauset Beach (ocean) and 3 mi. to Skaket Beach (bay). Five minute walk to town to enjoy great restaurants, coffee and ice cream shops, boutiques, access to Rail Trail (bike path), farmers market, Firebirds baseball games, galleries and more. Also, boat rentals/charters and golf nearby!

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!