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 1015 accommodations in Chatham, MA, here are the 4 best family friendly rentals

Compound On Historic Bank St Near Wychmere Club - Chatham, MA
10 39 reviews
Chatham, MA
09/07 – 13/07
SG$4151/nighttotal: SG$16604 (4 )

Compound On Historic Bank St Near Wychmere Club

7 6
apartment , Harwich
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.
Beachside Retreat! Cozy 1-bedroom W/ Private Yard - Chatham, MA
10 1 review
Chatham, MA
04/08 – 08/08
SG$878/nighttotal: SG$3512 (4 )

Beachside Retreat! Cozy 1-bedroom W/ Private Yard

1 2
apartment , Dennis
This Dennis beach house, a short walk from Haigis Beach and Sea Street Beach, offers easy access to Cape Cod's coastline and is under 3.2km from Swan Pond River and Bass River Lighthouse.
The 56 square metre property comprises one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private garden, patio, and free Wi-Fi.
Two-story Home W/new Kitchen, Washer/dryer, Large Yard, & Pool Table - Chatham, MA
9.4 20 reviews
Chatham, MA
04/08 – 08/08
SG$1792/nighttotal: SG$7168 (4 )

Two-story Home W/new Kitchen, Washer/dryer, Large Yard, & Pool Table

3 2
apartment , Orleans
This family-friendly apartment in East Orleans is located just a short drive from downtown Orleans' amenities and offers tranquil private access to Pochet Bay, ideal for nature lovers and water activities.
This spacious 187 square meter residence accommodates up to 8 guests across 3 bedrooms and 3 bathrooms, featuring a newly remodelled kitchen, a den with a pool table, a furnished deck, and a first-floor suite with accessibility features.
Harwich Escape  Deck, Firepit & Near Beaches - Chatham, MA
Chatham, MA
04/08 – 08/08
SG$1496/nighttotal: SG$5984 (4 )

Harwich Escape Deck, Firepit & Near Beaches

3 2
apartment , Harwich
This 152 square metre holiday home in Harwich offers three bedrooms and two bathrooms, accommodating up to eight guests and is conveniently located 700 metres from Pleasant Road Beach, with easy access to local dining and shops in Harwich Port.
This family-friendly property boasts air conditioning, a well-equipped kitchen with a dishwasher, and a private garden with a deck and gas grill, providing ample space for relaxation and outdoor activities, including proximity to Sand Pond and the Cape Cod Rail Trail for further adventures.

Best Chatham, MA holiday rentals with a pool

Among the 1015 accommodations in Chatham, MA, here are the 4 best rentals with a pool

Wequassett Resort And Golf Club - Chatham, MA
9.3 348 reviews
Chatham, MA
03/07 – 11/07
SG$3104/nighttotal: SG$24832 (8 )

Wequassett Resort And Golf Club

1 4
resort , Harwich
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.
Pleasant Bay Village Resort - Chatham, MA
9.6 458 reviews
Chatham, MA
25/06 – 27/06
SG$665/nighttotal: SG$1330 (2 )

Pleasant Bay Village Resort

1 4
resort , Chatham
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.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.3 2767 reviews
Chatham, MA
04/08 – 08/08
SG$962/nighttotal: SG$3848 (4 )

The Mansion At Ocean Edge Resort & Golf Club

1 2
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.
Ocean Mandevilla - Chatham, MA
9.0 44 reviews
Chatham, MA
15/07 – 17/07
SG$1211/nighttotal: SG$2422 (2 )

Ocean Mandevilla

2 2
apartment , Brewster
This two-bedroom apartment in Brewster is just 2.1 kilometres from Ellis Landing Beach and 2.9 kilometres from Linnell Landing Beach, offering easy access to the beautiful coastline. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, a terrace or balcony, and a private garden. Guests can enjoy a range of amenities including a swimming pool, a Jacuzzi, a sauna, a spa, a fitness centre, a tennis court, and free parking.

Frequently asked questions about holiday rentals in Chatham, MA

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Best Chatham, MA holiday rentals with a balcony

Tjs Tide: Prime Location Condo W/ Outdoor Deck - Chatham, MA
9.9 40 reviews
Chatham, MA
25/06 – 27/06
SG$1603/nighttotal: SG$3206 (2 )

Tjs Tide: Prime Location Condo W/ Outdoor Deck

2 4
apartment , Harwich
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.
Pelham House Resort - Chatham, MA
8.8 385 reviews
Chatham, MA
15/07 – 17/07
SG$1245/nighttotal: SG$2490 (2 )

Pelham House Resort

1 2
resort , Dennis
The Pelham House Resort is located in Dennis Port, just a short drive from the ferry to Nantucket Island and nearby golf courses. This resort enjoys excellent ratings for its location, cleanliness, and overall experience.
The resort has a private beach along Nantucket Sound and an outdoor pool with ocean views. Guests can enjoy modern amenities, including air conditioning, walk-in showers, and free Wi-Fi, as well as a bar and restaurant on-site.
Dolce Vita: Luxury Condo With Rooftop Terrace - Chatham, MA
Chatham, MA
25/06 – 27/06
SG$1721/nighttotal: SG$3442 (2 )

Dolce Vita: Luxury Condo With Rooftop Terrace

1 4
house , Harwich
Dolce Vita, a Harwich Port holiday home, is a 7-minute walk from Bank Street Beach and within 19-43km of attractions including Nauset Lighthouse, Wellfleet Bay Wildlife Sanctuary, and Heritage Museums & Gardens.
This two-bathroom property sleeps nine guests and features a well-equipped kitchen with dishwasher, microwave, and fridge; air conditioning; and internet access; it's also pet-friendly.
Guest House Ocean Whisper - Chatham, MA
9.7 4 reviews
Chatham, MA
25/06 – 27/06
SG$1575/nighttotal: SG$3150 (2 )

Guest House Ocean Whisper

4 4
house , Harwich
Guest House Ocean Whisper is a beachfront property located in Harwich, just 19 kilometres from Wellfleet Bay Wildlife Sanctuary and 19 kilometres from Nauset Lighthouse. The house has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom holiday home spans 112 square metres and can comfortably accommodate up to 13 guests. The property offers a range of amenities, including a fully equipped kitchen, a private balcony, a garden, and parking.

Best Chatham, MA holiday rentals with parking

4 Bedrooms, 2 Baths, Sleeps 8-10 - Chatham, MA
9.8 77 reviews
Chatham, MA
04/08 – 08/08
SG$1115/nighttotal: SG$4460 (4 )

4 Bedrooms, 2 Baths, Sleeps 8-10

4 2
apartment , Chatham
This four-bedroom holiday home is located in Chatham, within a short distance of both the Chatham Drama Guild and the Chatham Shark Centre, both less than 2 kilometres away.
The property boasts a spacious 167 square metre floor area, offering comfortable accommodation for up to eight guests and features a fully equipped kitchen, a terrace, a garden, and private parking.
Cozy Mid-cape Studio Steps To The Beach & Pool - Chatham, MA
10 6 reviews
Chatham, MA
15/07 – 17/07
SG$460/nighttotal: SG$920 (2 )

Cozy Mid-cape Studio Steps To The Beach & Pool

1 2
studio , Dennis
This Dennis, Massachusetts seaside apartment is located within a 1.6km walk of Haigis Beach and Sea Street Beach, and under 3.2km from Swan Pond River and Bass River Lighthouse.
The self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private patio, swimming pool, spa, and on-site water park.
Cape Cod Home With Space For Everyone - Chatham, MA
Chatham, MA
04/08 – 08/08
SG$2692/nighttotal: SG$10768 (4 )

Cape Cod Home With Space For Everyone

1 2
house , Dennis
This Cape Cod residence in Dennis is situated 1.8 kilometres from Sea Street Beach and is conveniently positioned for travel, being 13 kilometres from Cape Cod Gateway Airport.
This property offers 228 square metres of living space with one bedroom and four bathrooms, accommodating up to 27 guests with free WiFi, air conditioning, and a fully equipped kitchen.
Cozy Apartment On A Private Horse Farm Near The Beaches And Forest Conservation - Chatham, MA
9.4 32 reviews
Chatham, MA
04/08 – 08/08
SG$597/nighttotal: SG$2388 (4 )

Cozy Apartment On A Private Horse Farm Near The Beaches And Forest Conservation

1 2
apartment , Brewster
This one-bedroom apartment in West Brewster is ideally situated within 5 km of Cape Cod Beaches, the Cape Cod Museum of Natural History, and Breakwater Beach. The apartment offers a terrace, a garden, and parking, and is equipped with a fireplace, free WiFi, and a fully-equipped kitchen.
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