Compare Vacation Rentals & Airbnb in Chatham, MA

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Chatham, MA vacation rentals
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1379 Rentals and Airbnb in Chatham, MA

Best family friendly Chatham, MA vacation rentals

Among the 1379 accommodations in Chatham, MA, here are the 4 best family friendly rentals

Cozy Large Home W/ Patio Near Wequassett Resort - Chatham, MA
9.8 53 reviews

Cozy Large Home W/ Patio Near Wequassett Resort

apartment, Harwich
This yacht is situated in East Harwich, just 2km from downtown Chatham and Harwich, and about 3km from Jackknife Beach, offering a peaceful retreat close to the action. The vessel offers 3 bedrooms and 2 bathrooms, comfortably accommodating up to 10 guests. The yacht includes a fully equipped kitchen, a spacious garden, and access to high-speed WiFi, ensuring a comfortable and enjoyable stay.
Town Center-steps To Shops-walk To Beach-2026 Reno - Chatham, MA
10 17 reviews

Town Center-steps To Shops-walk To Beach-2026 Reno

apartment, Chatham
This two-bedroom, one-bathroom cottage in Chatham offers a prime location on Main Street, just 100 metres from downtown amenities and the beach shuttle, boasting an exceptional walkability score. The cottage provides accommodation for up to four guests and includes a dedicated parking space, a modern kitchen with a built-in oven and stove, a washer/dryer, and complimentary beach chairs and umbrellas, ensuring a comfortable stay with easy access to Lighthouse Beach and local shops.
Spacious Open Plan With Fenced Yard And Modern Amenities - Charming Oasis - Chatham, MA
No reviews

Spacious Open Plan With Fenced Yard And Modern Amenities - Charming Oasis

house, Chatham
This ranch-style property is situated in Chatham, approximately 2.9 kilometres from Ridgevale and Harding's Beaches, and a short drive to Main Street attractions.
This family-friendly accommodation offers one-level living for up to 8 guests, featuring a fully fenced yard ideal for children and dogs, an updated kitchen with a gas range, and complimentary daily tickets to local attractions through Xplorie, such as Island Cruises and Whale Watch.
The Boarding House. Steps From Ice Cream Shop - Chatham, MA
10 76 reviews

The Boarding House. Steps From Ice Cream Shop

apartment, Chatham
This charming house is situated just 1.6km from the Chatham Chamber of Commerce and Cape Cod Beaches, offering a prime location for exploring the area. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property spans 149 square metres and comfortably accommodates up to 8 guests across its four bedrooms. Guests can enjoy a range of amenities, including a private garden, barbecue grills, and a fully equipped kitchen, making it perfect for families and groups seeking a relaxing and enjoyable stay.

Best Chatham, MA vacation rentals with a pool

Among the 1379 accommodations in Chatham, MA, here are the 4 best rentals with a pool

Relaxing Fairway Escape With Resort Pools, Club Access, & Steps To Arbor Pool - Chatham, MA
10 1 review

Relaxing Fairway Escape With Resort Pools, Club Access, & Steps To Arbor Pool

apartment, Brewster
This spacious 139 square metre flat offers a prime location within Ocean Edge Resort, Brewster, directly on the 9th fairway and a 300-metre walk to the Arbor Pool and Ocean Edge shuttle stop for access to Crosby Landing Beach.
This family-friendly condo accommodates eight guests with three bedrooms and two bathrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, plus air conditioning, a swimming pool, jacuzzi, garden, sauna, and spa, with optional resort passes providing access to tennis, pickleball, bike rentals, kayaks, and paddleboards.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.2 96 reviews

The Mansion At Ocean Edge Resort & Golf Club

manor house, Brewster
The Mansion at Ocean Edge, a resort in Brewster, offers direct beach access and is located 15.8 kilometres from Mayflower Beach and 1.2 kilometres from Ocean Dunes Golf Club.
This family-friendly resort provides an on-site spa, multiple dining options including a restaurant with garden views and a bar, a swimming pool, a fitness centre, and tennis courts, with complimentary parking available.
229 M² House ∙ 4 Bedrooms ∙ 8 Guests - Chatham, MA
No reviews

229 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Harwich
This Harwich holiday home is located within easy reach of Harwich Port's shops and restaurants, and approximately 2.9 kilometres from Jacknife Beach.
This 228 square metre dwelling accommodates up to eight guests and includes four bedrooms, two bathrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a private swimming pool, hot tub, and complimentary daily tickets to local attractions through Xplorie, such as Island Cruises and Whale Watch tours.
Pool, Hot Tub, Water Views And More! - Chatham, MA
9.0 2 reviews

Pool, Hot Tub, Water Views And More!

apartment, Chatham
This waterfront estate in North Chatham is located 160 meters from a private neighbourhood beach and a short stroll to tranquil waterfront sands, with Chatham's Ridgevale and Hardings beaches a few kilometres away.
This spacious dwelling, covering 390 square meters, accommodates up to 18 guests with eight bedrooms and eight bathrooms, featuring a chef-calibre kitchen, a heated swimming pool, hot tub, and a game room with a pool table and bar.

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Best Chatham, MA vacation rentals with a balcony

Charming Dog Friendly North Chatham Ranch - Chatham, MA
10 2 reviews

Charming Dog Friendly North Chatham Ranch

apartment, Chatham
This pet-friendly holiday flat in North Chatham offers a seaside location, a 13-minute walk to Cape Cod Beaches and a 10-minute walk to the Chatham Shark Centre.
This 132 square metre apartment accommodates up to four guests, featuring two bedrooms, two bathrooms, a kitchen with a fridge, microwave oven and dishwasher, air conditioning, a terrace/balcony, garden, and on-site covered parking.
Chatham Village - Adorable Studio Apartment In Antique Home - Chatham, MA
9.4 100 reviews

Chatham Village - Adorable Studio Apartment In Antique Home

studio, Chatham
This Chatham apartment, less than 1.6km from Mayo House and Cape Cod beaches, offers easy access to local attractions including the Chatham Windmill and Atwood House Museum, all within a 24km radius.
The self-catering flat features one bedroom, one bathroom, sleeps two guests, and includes a kitchen with fridge and microwave, a terrace, free Wi-Fi, a parking space and access to a spa.
Dog Friendly, Game Room, Central Ac! - Chatham, MA
10 2 reviews

Dog Friendly, Game Room, Central Ac!

apartment, Chatham
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.
Cozy Large Home In Harwich With Patio Near Wequassett Resort - Chatham, MA
9.8 14 reviews

Cozy Large Home In Harwich With Patio Near Wequassett Resort

apartment, Harwich
This smoke-free holiday home, ‘Cozy Large Home In Harwich With Patio Near Wequassett Resort’, is situated in Harwich, within 5km of Cape Cod beaches, Captain's Cove Golf Course, and Adventure Chatham.
The 156 square metre property boasts three bedrooms, two bathrooms, sleeps nine guests, and includes a swimming pool, spa, barbecue facilities, and a fully equipped kitchen; on-site water park adds extra family fun.

Best Chatham, MA vacation rentals with parking

1 Mi To Sand! Mid-cape Chatham W/ Furnished Deck - Chatham, MA
9.2 12 reviews

1 Mi To Sand! Mid-cape Chatham W/ Furnished Deck

apartment, Chatham
This Chatham seaside property, near the Chamber of Commerce (1.9km) and Cape Cod beaches (2.4km), offers stunning ocean views and easy access to Ridgevale Beach and Adventure Chatham (within 3.2km).
This 187 square metre house sleeps eight, boasting three bedrooms, two bathrooms, a fully equipped kitchen, laundry facilities, a terrace, garden, parking, and a fireplace; barbecue grills are available for outdoor entertaining.
Cape Cod Classic Cottage Near Forest Beach - Chatham, MA
9.9 196 reviews

Cape Cod Classic Cottage Near Forest Beach

apartment, Chatham
This two-bedroom cottage is situated in a peaceful neighbourhood in Chatham, a short walk from Forest Beach and a short drive from the town centre.
The property boasts a modern interior with amenities such as a fully equipped kitchen, a 50-inch Samsung Frame TV with streaming services, and a private garden with a deck and a hammock, accommodating up to five guests.
Spacious W/ Large Outdoor Area Fire Pit! - Chatham, MA
9.4 109 reviews

Spacious W/ Large Outdoor Area Fire Pit!

apartment, Chatham
This seaside property is situated near Chatham, less than 1.6km from the Chatham Shark Center and Veterans Field, and within 3.2km of Gallery Antonia and Mayo House.
This 186 square metre house, sleeping eight guests, boasts four bedrooms, two bathrooms, a fully equipped kitchen, garden, terrace, parking, and in-house laundry facilities; enjoy ocean views and easy beach access.
Renovated Cottage 1 Mile To Beach In Chatham! - Chatham, MA
9.8 82 reviews

Renovated Cottage 1 Mile To Beach In Chatham!

apartment, Chatham
This Chatham bungalow, situated on a quiet street less than 3.2km from Chatham village centre and just over 1.6km from Ridgevale and Harding's Beaches, offers easy access to shops, restaurants, and the Old Colony Rail Trail.
The 65 square metre property features two bedrooms sleeping four, a fully equipped kitchen including a dishwasher, central air conditioning, a private outdoor shower, and a fenced garden with patio; Friday night band concerts are held in the nearby village centre.
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