Best Holiday rentals and Airbnb offers in Chatham, MA
Chatham, MA
15/07 – 17/07
SG$717/nighttotal: SG$1434 (2 )
Walk To Nantucket Sound Beaches! Family Getaway
3 2
house , Dennis
This Dennis Port holiday home is a short walk from Sea Street Beach, 34 kilometres from Nauset Lighthouse, and 37 kilometres from Heritage Museums & Gardens and Cape Cod National Seashore. This detached property offers 56 square metres of living space with 3 bedrooms and 1 bathroom, accommodating up to 9 guests with air conditioning, a fully equipped kitchen, free private parking, and an outdoor dining area.
Chatham, MA
04/08 – 08/08
SG$6294/nighttotal: SG$25176 (4 )
Dennis Family Oasis: Pool, Hot Tub, & Fire Pit!
1 2
apartment , Dennis
This Dennis Retreat is a six-bedroom, five-bathroom residence located in South Dennis, offering convenient access to Hyannis Harbour, Cape Cod's beaches, and Mayflower Beach, all within a few kilometres. This property provides accommodation for up to 10 guests, featuring a heated swimming pool, spa, sauna, and a firepit, alongside amenities such as air conditioning, a microwave oven, and a dishwasher, with parking included for your convenience.
9.3 3 reviews
Chatham, MA
25/06 – 27/06
SG$858/nighttotal: SG$1716 (2 )
Cape Escape - Family-friendly Chatham Retreat
2 4
apartment , Chatham
This Chatham holiday home, near Schoolhouse Pond (1 km) and a short drive from Hardings Beach (5.1 km) and Chatham town centre (4.2 km), offers convenient access to the Cape Cod Rail Trail (1.9 km). The two-bedroom, two-bathroom property sleeps four, features a fully equipped kitchen with dishwasher, a dedicated TV room with a sleeper sofa, and outdoor amenities including a patio, garden, and parking.
10 72 reviews
Chatham, MA
15/07 – 17/07
SG$798/nighttotal: SG$1596 (2 )
Dog Friendly Fenced In Yard! 3/2 1.1 Mi To Wifi - Perfect Fall Rental!
3 2
apartment , Chatham
This South Chatham holiday home is situated less than 1.6km from the Chatham Chamber of Commerce, Forest Beach, and Cape Cod Beaches, and within 4.8km of Cockle Cove and Ridgevale Beaches. This 111 square metre property offers three bedrooms, a sofa bed, two bathrooms, and sleeps eight guests, boasting a private garden, swimming pool, spa, fitness centre, and on-site water park.
9.5 105 reviews
Chatham, MA
15/07 – 17/07
SG$827/nighttotal: SG$1654 (2 )
South Chatham Sunshine
3 2
house , Chatham
This three-bedroom house is located in South Chatham, a short distance from Ridgevale Beach (2.4 kilometres), Cockle Cove Beach (2.6 kilometres) and Forest Beach, all within a 10-minute walk. The 138 square metre property features a fully equipped kitchen, a patio, a garden and parking, ideal for families or groups looking for a comfortable and convenient base to explore Chatham.
10 1 review
Chatham, MA
25/06 – 27/06
SG$1506/nighttotal: SG$3012 (2 )
Cozy Home Close To The Beach With Deck, Porch, W/d, & Foosball Table
4 4
apartment , Orleans
This holiday home is located in East Orleans, offering easy access to Cape Cod Beaches and the Cape Cod National Seashore, with Orleans Bowling Centre and Cape Escape Adventure Golf also nearby. Spanning 185 square meters, this residence accommodates up to eight guests with four bedrooms and five bathrooms, featuring a well-equipped kitchen, a comfortable living room with a television, a foosball table for entertainment, and a spacious porch and deck with views.
8.0 1 review
Chatham, MA
03/07 – 11/07
SG$1346/nighttotal: SG$10768 (8 )
Peaceful Patio Near Beach!
4 4
apartment , Chatham
35 John Street - Four Bedroom House is a 3-star self-catering property located 4km from Chatham town centre, near Chatham Chamber of Commerce, Cockle Cove Beach, and Ridgevale Beach. This four-bedroom house sleeps up to 10 guests and features air conditioning, a garden, and internet access; enjoy a peaceful residential setting with easy access to local beaches and amenities.
9.0 7 reviews
Chatham, MA
02/07 – 11/07
SG$702/nighttotal: SG$6318 (9 )
Harwich Home Close To The Beach
3 4
apartment , Harwich
This three-bedroom apartment in Northwest Harwich is ideally situated just a five-minute walk from Earle Road Beach and next to a golf course, offering a peaceful setting close to the coast. The property has received excellent user ratings, so you can be sure of a comfortable and enjoyable stay. The spacious home comfortably accommodates up to eight guests and features an open floor plan, perfect for families or groups. Enjoy a private backyard with a deck and outdoor shower, parking for three cars, a modern kitchen, and the convenience of a private beach access in addition to the nearby public beach.
9.6 10 reviews
Chatham, MA
15/07 – 17/07
SG$1322/nighttotal: SG$2644 (2 )
Ideally Located Home With Yard, Grill, Bikes, Gas Fireplace, Streaming, W/d, Ac
4 2
apartment , Brewster
This spacious apartment in West Brewster is a short drive from multiple beaches and situated near attractions such as the Cape Cod Museum of Natural History and Dennis Pines Golf Course. Offering 167 square meters of living space for up to 8 guests, this property features four bedrooms, four bathrooms, a fully equipped kitchen with granite countertops and stainless steel appliances, and an expansive outdoor space with a patio, grill, and yard games.
8.8 39 reviews
Chatham, MA
15/07 – 17/07
SG$1089/nighttotal: SG$2178 (2 )
The Spray
2 2
house , Harwich
The Spray is a 2-bedroom house located in Harwich Port, a short walk from Bank Street Beach and a short drive from Red River Beach, offering a peaceful escape from the town centre. Guests have consistently rated the property highly for its cleanliness, location, and overall experience. The house has a floor area of 67 square metres and can accommodate up to 5 guests. It is fully equipped with a kitchen, a terrace, a garden, and a spa, providing everything you need for a comfortable and enjoyable stay.
Chatham, MA
25/06 – 27/06
SG$891/nighttotal: SG$1782 (2 )
Ranch-style Retreat By Leavetown Vacations
3 4
house , Harwich
This ranch-style property is situated in Harwich, 19 kilometres from Cape Cod Gateway Airport, 23 kilometres from Nauset Lighthouse, and 26 kilometres from Wellfleet Bay Wildlife Sanctuary. This spacious 158 square metre dwelling accommodates up to 11 guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen with a dishwasher, air conditioning, a fireplace, and a terrace, with free WiFi provided.
9.8 19 reviews
Chatham, MA
09/07 – 13/07
SG$1417/nighttotal: SG$5668 (4 )
Jean's Dream - Renovated Chatham House
1 6
apartment , Chatham
This South Chatham holiday home, situated on Main Street (Route 28), is 1.45 km from Cockle Cove Beach and a short drive from Chatham's town centre, offering easy access to restaurants, shops, and attractions such as The Squire and Chatham Bars Inn. The newly renovated property sleeps up to 7 guests in 2 bedrooms and features an open-plan living/dining/kitchen area, a private backyard with a grill and outdoor games, ample parking, and direct access to the Cape Cod Rail Trail.
Best family friendly Chatham, MA holiday rentals
Among the 1015 accommodations in Chatham, MA, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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
What sports or outdoor activites can visitors enjoy in and around Chatham, MA?
Chatham is a great place for outdoor activities. You can go kayaking, paddleboarding, or windsurfing on the bay. You can also go fishing, hiking, or birdwatching in the surrounding areas. And, of course, there's always the beach for swimming, sunbathing, and building sandcastles.
What are the best Airbnb and vacation rentals in Chatham, MA?
What other towns or cities can be easily accessed from Chatham, MA?
From Chatham, you can easily reach other towns on Cape Cod, such as Harwich Port, which is about 15 minutes away, and Orleans, which is about 20 minutes away. You can also drive to Provincetown, which is about an hour away, and explore the tip of Cape Cod.
What amenities are commonly available in vacation rentals in Chatham, MA?
Most vacation rentals in Chatham have basic amenities like kitchens, bathrooms, and bedrooms. Many also have outdoor spaces like patios or decks, and some even have swimming pools or hot tubs. It's best to check the listing for specific amenities.
What are the best vacation rentals with a pool in Chatham, MA?
What time of year is best to rent a vacation rental Chatham, MA?
The best time to visit Chatham depends on your preferences. Summer is the most popular time to visit, but it can be crowded and expensive. If you prefer a quieter experience, you can visit in the spring or fall, when the weather is still pleasant and the crowds are smaller. The shoulder seasons are usually cheaper too.
What are the best rentals for families and kids in Chatham, MA?
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.
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.
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.
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
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.
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.
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.
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.