Vacation Rentals in Chatham, MA

This three-bedroom Harwich Port holiday home is situated on historic Bank Street, a short walk or cycle ride (less than 1km) from Bank Street Beach, Saquatucket Harbour, and the Wychmere Beach Club.
The self-catering property boasts a modern kitchen with dishwasher, three parking spaces, a garden with firepit and outdoor shower, plus beach essentials and an open-plan living area with a games table and a second living area that can be used as a third bedroom.

This Harwich flat is located on a tranquil residential street bordering conservation land, a 5 to 10-minute drive from Red River and Bank Street beaches, and within easy reach of Harwich and Chatham Centres for amenities.
This family-friendly maisonette offers 139 square meters of living space for up to 4 guests, featuring 2 bedrooms, 1 bathroom, central air conditioning, WiFi, a kitchen with a fridge, microwave, and dishwasher, a game room with ping-pong, and a patio with a firepit, with the Cape Cod Rail Trail nearby for outdoor pursuits.

Azure Cottage, situated in Chatham's Oyster Pond area, is less than 1.6km from Chatham town centre and under 3.2km from Chatham's beaches.
This three-bedroom, two-bathroom property sleeps eight, boasts a private 0.6-hectare garden, hot tub, swimming pool, and fitness centre, plus a $750 Xplorie package offering free local attraction tickets.

The Wequassett Resort And Golf Club is situated in Harwich, a short drive from the centre of town and close to Cape Cod National Golf Center and the stunning Cape Cod National Seashore. It has received excellent ratings for both its location and overall experience, with guests praising its cleanliness and friendly service.
The resort offers a range of accommodation options, from spacious rooms to luxurious suites, all featuring comfortable sitting areas and private decks or patios. Guests can enjoy a variety of amenities, including a swimming pool, hot tub, fitness centre, tennis court, and a restaurant serving delicious seafood and American classics.

This four-bedroom house in Chatham is situated 2.4 kilometres from Ridgevale Beach.
The property boasts a spacious layout, sleeping eight guests, with a private pool, hot tub, and fully fenced yard; it also includes a fully equipped kitchen and central air conditioning.

This apartment is situated within the historic town of Brewster, offering a prime location on Cape Cod, 2.3 kilometres from Ellis Landing Beach and 29 kilometres from the National Seashore, with Provincetown 51 kilometres away.
This 88-square-metre flat features two bedrooms and two bathrooms, accommodating up to six guests with an open-concept living and kitchen area, air conditioning, a swimming pool, and access to resort amenities.

The Pleasant Bay Village Resort is located in Chatham, Massachusetts, just 4 kilometres from the Chatham Railroad Museum and 3.2 kilometres from the Chatham Municipal Airport. The resort is a 4-star property that has received excellent user ratings for its location, cleanliness and overall experience.
The resort offers spacious rooms with floral décor and private patios. Guests can enjoy a range of amenities including a seasonal outdoor pool, hot tub, game room, playground, free Wi-Fi, laundry facilities, a fitness centre, a restaurant and room service.

Chatham Bars Inn is an oceanfront hotel in Chatham, Massachusetts, a short distance from the Chatham Lighthouse and the Chatham Bars. The hotel consistently receives excellent ratings for its location, user experience, and cleanliness.
The hotel offers a range of rooms and suites, all featuring modern amenities. Guests can enjoy a variety of on-site amenities and activities, including a heated pool, private beach access, a full-service spa, and several restaurants.

This two-bedroom apartment is situated in Harwich Port, a short walk from the beautiful Cape Cod Beaches and within a mile of Harwich Port and Allen Harbor Marina. Guests have consistently rated this property as excellent.
The apartment comfortably sleeps five guests and features a fully equipped kitchen, a fireplace, and a balcony. Enjoy the convenience of a swimming pool, a spa, and concierge services during your stay.

This five-bedroom, three-bathroom detached house in Brewster offers immediate access to the Cape Cod Rail Trail, Nickerson State Park, and Blueberry Pond, with bay beaches such as Breakwater Beach and Paine's Creek just minutes away.
This property boasts a spacious 0.7-acre private garden with a fire pit and Adirondack chairs, a jacuzzi tub in the master en-suite, an outdoor shower, and an open-plan upper-level living, dining, and kitchen space with vaulted ceilings and a gas fireplace, accommodating up to six guests.

This seven-bedroom house is located on a river in Orleans, just 0.16 kilometers from Nickerson State Park and within 5 kilometers of Orleans Bowling Center, Stony Brook Grist Mill, Skaket Beach, and Jonathan Young Windmill. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The house comfortably accommodates up to 26 guests and features a fully equipped kitchen, a garden, barbecue grills, and a terrace. Guests can enjoy stunning river views, relax in the tranquil surroundings, and explore the diverse ecosystem of Nickerson State Park, all within easy reach of Orleans' attractions and activities.

The Mansion at Ocean Edge Resort and Golf Club is located in Brewster, a short drive from the Cape Cod Museum of Natural History and the Wellfleet Drive-In Theater & Cinemas. It has consistently received very good ratings for location, cleanliness, and overall user experience.
The resort offers a range of accommodation options, including guest rooms with patios or balconies and villas with full kitchens and living rooms. Guests can enjoy a private beach, two swimming pools, a spa, a fitness centre, tennis courts, and a variety of dining options, including a pub, a tavern, and a seasonal terrace.

This Chatham holiday home is situated near Schoolhouse Pond, a short drive (approximately 1.6km) from Hardings Beach, Chatham town centre, Coast Guard Beach, and the Cape Cod Rail Trail.
The 110 square metre property boasts a two-bedroom, two-bathroom layout sleeping four guests, includes a fully equipped kitchen, spa, garden, parking, and the Xplorie $750 attraction pass.

This spacious eight-bedroom, five-bathroom dwelling is centrally located in Chatham town centre, a mere 644 metres from Andrew Harding's Beach and 966 metres from Lighthouse Beach, offering convenient access to Main Street amenities.
This property provides ample space for eighteen guests with a state-of-the-art kitchen, expansive outdoor living areas including a private garden with a grill, and complimentary daily tickets to local attractions through Xplorie.

This Dennis Port seaside cottage, an 8-minute (approximately 13 km) drive from Cape Cod Beaches and Sea Street Beach, offers stunning ocean views.
The 76 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, a garden with barbecue, free parking, Wi-Fi, and air conditioning.

This Harwich apartment, ideally located 0.5 km from Bank Street Beach and within walking distance of Main Street's shops and restaurants, offers easy access to Wychmere wedding venue (0.8 km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen, private deck with bocce and cornhole, beach essentials, and free Wi-Fi; weekly cleaning is provided for stays of two weeks or more.