Holiday rentals in Little Pleasant Bay

Chit-Chat Cottage on White pond, near DT/beaches.

Affectionately named the "Chit-Chat", this classic 1920's 2 bed 1 bath Cape Cod cottage is near downtown and steps from Chatham's best restaurants, attractions, and beaches. Relax with your morning coffee in the sunny living room while the gentle breeze flows through the numerous windows. Stroll down the path to White Pond to enjoy some sun, sand, and swimming or take a quick 5-10 minute drive to some of the Cape's best beaches. Come explore Cape Cod and create lasting memories at the Chit-Chat.

Chatham Center - Games & Firepit - Walk everywhere

Your family or group of friends will be close to everything when you stay at this centrally-located home. This cozy home is perfect for those looking to be walking distance to restaurants, boutiques, movie theater, baseball field, beach, & more! Enjoy 5 bedrooms, two decks, a spacious outdoor shower, & a finished basement filled with two seating areas & games. In Downtown Chatham .4 Miles to Oyster Pond Beach .3 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

Premium N. Chatham Getaway, A/C

Fully renovated N. Chatham home with a large yard and open kitchen/living area. Features 3 bedrooms with 4 queen beds, 2 full and 2 half baths, plus a walk-out finished basement. Enjoy hardwood floors, AC, 3 large TVs and WiFi. Short walk to local coffee shop, bakery, and liquor store. Close to downtown, lighthouse beach, and resturants. Perfect for families seeking a Cape Cod retreat. CBI/WEQ-5 minute drive. July-Early Sept: 7-night min, Sat-Sat. Off-Season: Flexible – contact for details.

Modern Cape Escape, Fire Pit, Sleeps 8 & Cental AC

➤ Relax by the Outdoor Fire, stay in for a Family Movie Night, or explore Orleans’ nearby Beaches/Shopping/Dining ➤ Central: ★ Walk to Pilgrim Lake ★ 5mins drive to Beaches/Shopping ➤ Nestled in the peaceful windswept woodlands of the Lower Cape, this bright & spacious home is the ideal place for calm, connection & conversation ➤ A favorite of Family Holidays, Friends groups & Freelancers, this recently-renovated Orleans acreage transports you to a simpler time-where stress is left behind.

The Wellfleet Beach House. Sleeps 6

On the road to Cape Cod's most loved beaches at the National Seashore. Come around the corner and pull into this property and you will instantly feel at home. This little gem is a three-bedroom Cape style with two bedrooms upstairs and a full bath with a walk-in shower. You will find another full bedroom and bath w/tub on the first floor. Open living/dining room & great kitchen. This property offers comfort and privacy with a level spacious backyard, firepit & outdoor shower.

Your private, in village, Pied-a-Terre.

Great in-town location. Bright, Clean, Safe, Private and Spacious. Hidden away Above the shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Well equipped Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

Nauset Heights Cottage- 5 minute walk to beach!

Charming three bedroom completely renovated Cape cottage that sleeps six with a large open kitchen, deck with seating, and a grill. Large private yard sheltered by trees has room for croquet and corn-hole, as well as a secluded outdoor shower. The house has beach chairs, boogie boards, and sand toys available for your beach days! Downtown Orleans is an 8-minute drive away; North Nauset Beach, Priscilla Beach, and the Mill Pond are all a five minute walk away!

Spacious Pet Friendly Cape, Large Yard

Our home is located in a quiet neighborhood close to beaches, golf courses and bike trails. It is a short drive to Chatham town center and is the perfect location to be close to all attractions but secluded enough to unwind. Take advantage of the outdoors on a new deck and large backyard. Large, mature plants and trees surround the property on three sides. Blackberry, raspberry and blueberry bushes in the backyard provide ripe fruit in the summer months.

Newly remodeled cottage with path to beach

Enjoy the brand new kitchen and furniture in this newly remodeled cottage, The Sandpiper. The property is conveniently located next to Spruce Hill Conservation area allowing you direct access to trails that lead to Spruce Hill Beach (.3 miles). Bike directly to Cape Cod Rail Trail (.3 miles) or Nickerson State Park (less than 1 mile). Have your fish and chips or lobster rolls across the street at Cobies, or enjoy our local coffee shops and fine dining.

Cheerful 2 bedroom home walk to town location.

Adorable house in a quiet neighborhood close to all that Chatham has to offer. Walk to town, restaurants, Chatham A's baseball field, Chatham Bars Inn. Quick walk/bike to Cape Cod Rail Trail. Short drive or bike ride to beaches. House is equipped with all you need for relaxing nights at home including fire pit, patio and grill.

Quaint Downtown Chatham Home

This charming and totally renovated Chatham home is on a private road in a downtown neighborhood of exclusive homes. Its ideal location enables you to walk to Lighthouse Beach about (1/2 mile) and 1 block from downtown Chatham. Also, the house is a quick walk to Children's Beach (Oyster Pond).

The Clam Nest

The Clam Nest is a bright, clean, craftsman-owned home with tile floors, an open floor plan, and all the essentials of home located convenient to both bay and oceanside amenities and beaches. Perfect for couples and families.