Compare Vacation Rentals & Airbnb in Chatham, MA

This waterfront property offers direct access to Lover's Lake in central Chatham, with Jackknife Beach and Harding's Beach a short 5-minute drive away.
This 4-bedroom cottage comfortably sleeps 9 guests and features a newly renovated kitchen, a downstairs games room, and multiple outdoor seating areas, ideal for families seeking a lake and beach holiday.

This spacious Cape Cod house, located in the Cannon Hill Association of North Chatham, offers direct access to a private beach and is a short distance from Pleasant Bay.
The 234 square metre (2517 square feet) property boasts four bedrooms, four bathrooms, sleeps up to ten guests, and includes a fully equipped kitchen, spa, fitness centre, and complimentary access to local attractions via the Xplorie offer.

This Chatham apartment, ideally located near White Pond and with direct access to the Chatham bike path, offers easy access to beaches and the town centre, all within a short walk or cycle.
The three-bedroom, two-bathroom property sleeps six, boasts a fully equipped kitchen including a lobster pot, an indoor games room with ping pong and foosball, and extensive outdoor space with a deck, gas grill and fire pit; pet-friendly with a £40 fee.

This Chatham, Massachusetts holiday home is situated on the shores of Goose Pond, 4.2km from Chatham's town centre and its attractions, including the Orpheum Theatre and Chatham Bars Inn, and within 1.6km of local shops and restaurants.
This 80 square metre self-catering property sleeps four guests in one bedroom and one bathroom, boasting a recently updated kitchen and bathroom, a spa, fitness centre, free Xplorie tickets for local attractions, and two kayaks for use on Goose Pond, plus keyless entry and direct beach access.

This spacious five-bedroom apartment is located in Chatham, offering easy access to local attractions including an 11-minute walk to the Chatham Drama Guild and a 3-minute drive to Cape Cod Beaches.
This family-friendly property boasts a floor area of 255 square metres, accommodates up to 12 guests, and features a private swimming pool, a terrace with barbecue facilities, air conditioning, and Wi-Fi.

This luxurious seven-bedroom house is situated in a quiet neighbourhood just 12 kilometres from the centre of Orleans, providing easy access to the city's attractions, including the Château de Chambord, a 20-minute drive away. This property has consistently received excellent ratings for its location, cleanliness and overall experience.
The house spans four floors and covers 365 square metres. It offers a range of amenities, including a private swimming pool, a sauna, a hot tub, a large garden, and a fully equipped kitchen.

This apartment is situated on the 9th fairway of the Ocean Edge Golf Club in Brewster, just a short distance from the beach and the Rail Trail Bike Shop. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This 139 square metre apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The apartment offers a range of amenities, including a fully equipped kitchen, a swimming pool, a spa, a terrace, parking, and access to the Ocean Edge Resort amenities, making it a great choice for a relaxing and enjoyable stay in Brewster.

This luxury residence in Chatham Port is located 2.4 kilometres from Scatteree Beach and 22.5 kilometres from Nauset Lighthouse.
This spacious 361 square meter property accommodates up to 23 guests and features six bathrooms, a well-equipped kitchen with a dishwasher, oven, and microwave, air conditioning, a swimming pool, a hot tub, a garden, parking, free WiFi, and a fireplace, with an on-site water park and outdoor seating offering sea views from its patio.

This 138 square meter, family-friendly apartment in Chatham is situated just 250 meters from Main Street, offering easy access to its restaurants, art galleries, and boutiques, and is a short drive to Ridgevale Beach (2.4 km), Harding Beach (2.4 km), and Lighthouse Beach (4.8 km).
This accommodation sleeps six guests and features dual living areas, a private deck with a gas grill, complimentary Wi-Fi, and is located 400 meters from the Old Colony Rail Trail, ideal for exploring Cape Cod's terrain.

This Chatham house is located just a 2.4 kilometre walk from the Chatham Shark Center and Cape Cod Beaches, and a 3.2 kilometre drive from Fox Hill and Chatham Fish Pier, making it a great base for exploring the area. The property has excellent user, location and cleanliness ratings.
The house has 4 bathrooms and is 325 square metres in size. It features a fully equipped kitchen, garden, terrace, air conditioning, parking and free Wi-Fi, as well as a washing machine, coffee/tea maker, and a TV.

This pet-friendly holiday home is located in Chatham, a short drive from Cape Cod Beaches and the Chatham Shark Centre, offering proximity to maritime activities.
This spacious 204 square metre holiday home accommodates up to 8 guests with 4 bedrooms and 3.5 bathrooms, featuring air conditioning, Wi-Fi, a private garden, and a balcony with a barbecue and fire pit.

This Chatham holiday flat is located at the end of a quiet road, 400 metres from Main Street and Oyster Pond, offering subtle views of Oyster Pond.
This 153 square metre residence accommodates up to six guests with three bedrooms and two bathrooms, featuring a rear patio, on-site washer/dryer, and mini-split air conditioning.

This fully renovated Cape Cod residence in South Chatham offers an apartment for rent, situated just 160 metres from the Cape Cod Rail Trail and less than 1 kilometre from several beaches.
This spacious 3-bedroom, 2-bathroom apartment accommodates up to 7 guests, featuring a chef's kitchen, private sauna, cold plunge, roof deck, gas grill, fire pit, outdoor shower, and a newly finished basement with a home gym and game room.

This Chatham Cape Cod house, situated 1.6km from Ridgevale Beach and close to a bike trail, offers easy access to Chatham's town centre and other Cape Cod attractions.
This three-bedroom, two-bathroom property boasts 187 square metres of floor space, sleeps up to 15 guests, and includes amenities such as a fully equipped kitchen, air conditioning, Wi-Fi, and a garden with outdoor dining.

This Chatham apartment, conveniently located in central Chatham, is within a 2.4km walk of Mayo House, Chatham Lighthouse Beach, and Gallery Antonia, offering easy access to Cape Cod beaches.
The 56 square metre self-catering flat features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, free parking, and air conditioning.

This classic Cape Cod beach house is situated just steps from the ocean, offering panoramic views across the protected marsh and is located within 16 kilometres of Chatham's shops, restaurants, and town centre. The two-bedroom property sleeps five guests and includes a private back cottage, modern amenities, and a garden, making it ideal for families or groups seeking a relaxing seaside retreat.