Holiday Rentals in Chatham, MA

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Chatham, MA holiday rentals
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Best Holiday rentals and Airbnb offers in Chatham, MA

Best family friendly Chatham, MA holiday rentals

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

Breathtaking Riverfront Home With A Lovely Deck, Close To Beach - Dogs Ok - Chatham, MA
10 1 review

Breathtaking Riverfront Home With A Lovely Deck, Close To Beach - Dogs Ok

apartment, Chatham
This Chatham waterside flat boasts panoramic views of Oyster River and is situated 1.6 kilometres from Harding's Beach and 3.2 kilometres from downtown Chatham.
This 100 square metre apartment accommodates up to six guests and features a wrap-around deck with a grill, a fully equipped kitchen, air conditioning, and WiFi, with beach chairs and toys provided for your use.
Large Home W/ Fire Pit And Dogs Welcome! - Chatham, MA
No reviews

Large Home W/ Fire Pit And Dogs Welcome!

house, Chatham
This detached house is situated in Chatham, 1.1 kilometres from Goose Pond.
This family-friendly property accommodates up to 10 guests across four bedrooms and features a well-equipped kitchen, air conditioning, WiFi, a deck with outdoor dining, and a fire pit, with dogs welcome for a nightly fee.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.3 2648 reviews

The Mansion At Ocean Edge Resort & Golf Club

resort, Brewster
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.
Quaint Chatham Home W/beautiful Backyard & Furnished Multi-level Deck, Dogs Ok - Chatham, MA
9.6 105 reviews

Quaint Chatham Home W/beautiful Backyard & Furnished Multi-level Deck, Dogs Ok

apartment, Chatham
This Chatham holiday flat is located approximately 1.6 kilometres from Hardings Beach and just over 3.2 kilometres east of Chatham's shops and restaurants, with the Barn Hill boat launch 400 metres away.
This 91 square metre apartment accommodates up to six guests, featuring two bedrooms, one bathroom, a gas fireplace, a well-equipped kitchen, and a landscaped garden with a multi-level deck, plus beach gear available for use.

Best Chatham, MA holiday rentals with a pool

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

Ocean Edge Luxury Condo,  Constantly Updated, Just Steps To Arbor Pool - Chatham, MA
10 135 reviews

Ocean Edge Luxury Condo, Constantly Updated, Just Steps To Arbor Pool

apartment, Brewster
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.
The Barn At Chatham Oaks - Chatham, MA
9.4 13 reviews

The Barn At Chatham Oaks

apartment, Chatham
This Chatham holiday home is situated near the sea, less than 2km from the Chatham Chamber of Commerce and Cape Cod beaches, with Ridgevale Beach and Cockle Cove Beach also within 3km.
This 372 square metre property boasts seven bedrooms, five bathrooms, sleeps sixteen guests, and includes a private pool, sauna, and fully equipped kitchen; free Wi-Fi is also provided.
New August Availability  Ocean Edge Passes Available For Fee   Central A/c - Chatham, MA
9.4 67 reviews

New August Availability Ocean Edge Passes Available For Fee Central A/c

apartment, Brewster
This newly remodelled three-bedroom townhouse is situated within the esteemed Ocean Edge Resort in Brewster, providing easy access to local beaches, golf courses, and biking trails.
This family-friendly accommodation, spanning 111 square metres and accommodating up to six guests, boasts a modern kitchen, central air conditioning, a private patio with a barbecue, and complimentary use of four beach chairs, with optional resort passes available for pools and fitness facilities.
Luxury Home With Pool, Hot Tub & Water View - Chatham, MA
10 3 reviews

Luxury Home With Pool, Hot Tub & Water View

apartment, Chatham
This five-bedroom, six-bathroom waterside residence in North Chatham offers prime waterfront positioning, just 990 metres from the Chatham Shark Centre and 1.2 kilometres from the Chatham Marconi Maritime Centre, providing convenient access to local maritime attractions and nearby beaches.
Spanning 361 square metres, this spacious holiday home accommodates up to 12 guests and features a well-equipped kitchen, air conditioning, Wi-Fi, a garden, a communal swimming pool, a hot tub, and on-site parking, ideal for exploring the area on foot.

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Best Chatham, MA holiday rentals with a balcony

Lucky Number Seven - Chatham, MA
8.8 11 reviews

Lucky Number Seven

house, Chatham
Lucky Number Seven is a 2-bedroom house located in Chatham, Massachusetts, just 1.6km from Ridgevale Beach and 1.8km from Harding Beach. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 91 square metre house comfortably sleeps 6 guests. The property features a fully equipped kitchen, air conditioning, a swimming pool, a garden, a spa, and parking, as well as free Wi-Fi and access to nearby cycling routes.
Riviera Sunset - Chatham, MA
9.2 7 reviews

Riviera Sunset

house, Chatham
The Riviera Sunset is a beachfront apartment in Chatham, located a short walk from Chatham Lighthouse Beach and a drive from Cape Cod National Seashore.
The 52 square metre apartment features two living rooms, a fully equipped kitchen, a private entrance, and can accommodate up to seven guests.
Beautiful Home W Artistic Flair - Chatham, MA
10 1 review

Beautiful Home W Artistic Flair

house, Chatham
This Chatham holiday home is situated within 2.4-2.7 km of Ridgevale and Cockle Cove Beaches, and under 3.2 km from Forest Beach, offering easy access to these beautiful coastal spots.
The 143 square metre property boasts three bedrooms, three bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen, laundry facilities, Wi-Fi, and a private garden; nearby attractions include Cape Cod National Seashore, Truro Historical Museum, Nauset Lighthouse, and Wellfleet Bay Wildlife Sanctuary.
Waterfront Escape, Game Room, Dog Friendly! - Chatham, MA
No reviews

Waterfront Escape, Game Room, Dog Friendly!

apartment, Chatham
This waterfront residence in West Chatham offers direct sea access and panoramic water views, situated approximately 1.0 kilometre from Harding's Beach and Ridgevale Beach, and a short drive to Chatham's amenities.
This spacious 465 square metre holiday home features 6 bedrooms and 4 bathrooms accommodating up to 12 guests, with a basement games room, outdoor dining deck, wood fire pit, and is dog-friendly.

Best Chatham, MA holiday rentals with parking

Chatham Rose Arbors Artist Cottage - Chatham, MA
9.8 89 reviews

Chatham Rose Arbors Artist Cottage

house, Chatham
This Chatham studio cottage, a short 3.2km drive from Chatham's beach and directly adjacent to the Cape Cod Rail Trail, offers a convenient base for exploring the area.
The self-catering property sleeps two, includes two bikes, kayaks with roof straps, a gas grill, and features a full bathroom, outdoor shower, air conditioning, parking for two cars, and excellent guest reviews.
Chatham Charmer - Chatham, MA
10 197 reviews

Chatham Charmer

apartment, Chatham
This Chatham cottage, situated 1.6km from the town centre and 4km from Chatham's beaches, offers easy access to the town's shops, restaurants, and the scenic bike trail.
The 2-bedroom property sleeps 4, features a modern open-plan layout, a fully equipped kitchen with dishwasher, and includes amenities such as adult bikes, beach equipment, and outdoor dining furniture.
Close To Everything In Chatham - Chatham, MA
9.9 216 reviews

Close To Everything In Chatham

apartment, Chatham
This four-bedroom, two-bathroom house in Chatham, Massachusetts, is situated between the Chatham Bars Inn and Wequassett Resort, less than 1.6km from Scatteree Beach and 1.9km from the town centre.
Sleeping up to ten guests, this three-story property boasts a newly remodelled kitchen and bathrooms, two living rooms with cable TV, a garden with a deck, patio, and gas grill, plus WiFi, a washer/dryer, and beach towels.
Newly Renovated Modern Pond Access! - Chatham, MA
9.9 119 reviews

Newly Renovated Modern Pond Access!

apartment, Chatham
This three-bedroom house is situated in Chatham, within 1.6 kilometres of the Chatham Chamber of Commerce and the beautiful Cockle Cove Beach.
The 157 square metre property boasts a fully equipped kitchen, two bathrooms, a fireplace, and a garden with barbecue facilities, comfortably accommodating up to eight guests.
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