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.

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

Large Sunny Deck, Harbor View, Walk to Town.

Classic little Cape cottage in an ideal location. Less than ten minute drive to amazing ponds and bayside or ocean beaches. Views of the harbor from the large sunny deck with attached outdoor shower. Ten minute walk into town along Duck Creek marsh & over scenic Uncle Tim’s Bridge. Visit the shops & galleries, have lunch or grab a drink at one of the many restaurants in town. Walk to the fish market and come home grill dinner on the deck. 15 minutes bike ride to the closest ocean beach.

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!

Close to Beach Renovated Dog Friendly Cape Cottage

Welcome to our enchanting Cape Cottage in the heart of Chatham, where timeless charm meets modern comfort. 4 minutes from the beach and nestled on a spacious half acre, this newly revitalized and renovated home provides an authentic Cape Cod vacation experience. As you step into our home, you'll immediately sense the true heart and soul of a Cape Cod getaway. Our cottage boasts a warm and inviting atmosphere, perfect for families, couples, or friends seeking a luxurious escape to Chatham.

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

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.

Wequasset House - Quiet, spacious beach base

No cleaning fees! Keep it simple at this peaceful and centrally-located furnished home base for your Cape Cod adventures! Cozy 3-bed, 2-bath ranch house with deck. 3pm check in & 10am check out All rooms have end tables with built in charging. Bedrooms have window AC units & mini split in living room. Coffee station in kitchen with KCups refreshed in May New for 2026: 1. New larger living room couch 2. Couch in bunk bedroom 3. TV with Roku added to master bedroom

Hillside Cottage

A one-bedroom cottage that sleeps 4, nestled into the hillside at the top of the wetland. Great for birding! Located on a beautifully landscaped property walking distance to Lecount Hollow Beach. The bedroom has a queen bed and there is a queen and a single sleep sofa in the finished basement. There is also a studio apartment available on the premises that sleeps two. The listing name is "Comfortable Studio Apartment".(Pets are allowed in the studio appartment)

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.

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

Cozy Condo/Cottage on Cove, Walk to Town

Welcome! Enjoy a Fabulous 180 degree water view out our master bedroom and living room. Walk to Orleans village, art galleries, restaurants & shopping. Bike to Beaches and baseball all within a mile. One floor condo is good for couples, solo adventurers, small families. One full bath with shower and one half bath, plus a new outdoor shower. Master BR has Queen bed. Second BR has a queen bed with a twin trundle pull out.