Best Vacation rentals and Airbnb offers in Chatham, MA
9.8 77 reviews
Chatham, MA
08/04 – 08/08
$868/nighttotal: $3472 (4 )
4 Bedrooms, 2 Baths, Sleeps 8-10
4 2
apartment , Chatham
This four-bedroom vacation rental is conveniently located in Chatham, Massachusetts, within a mile of the Chatham Drama Guild and Chatham Shark Center. The 1,800 square foot home offers a spacious and comfortable setting for families or groups of up to eight guests, featuring modern amenities such as free WiFi, a Smart TV, a refrigerator, and a washing machine, as well as a patio for outdoor relaxation.
10 3 reviews
Chatham, MA
08/07 – 08/14
$1715/nighttotal: $12005 (7 )
Slow M’ocean – A Fresh Take On Cape Calm
3 7
apartment , Chatham
This three-bedroom, three-bathroom Chatham rental is located in a residential neighborhood, half a mile from the Chatham Lighthouse and 1.3 miles from downtown Chatham, offering easy access to Lighthouse Beach and the town's attractions. The 3-bedroom home features stunning ocean views, a wraparound deck, keyless entry, a fully equipped kitchen with dishwasher, central A/C, Wi-Fi, laundry facilities, a gas grill, fire pit, ping pong table, enclosed outdoor shower, and can comfortably accommodate up to eight guests.
10 3 reviews
Chatham, MA
06/25 – 06/27
$938/nighttotal: $1876 (2 )
Peaceful Beach Retreat: Private Yard, Close To Beaches, Chatham & Rail Trail
2 4
apartment , Harwich
This Harwich condo is located on a quiet residential street near conservation land, offering a 5 to 10-minute drive to Red River and Bank Street Beaches, and easy access to Chatham and Harwich Centers. This 1500 square foot rental accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring central air conditioning, WiFi, a well-equipped kitchen, a game room with ping-pong, and outdoor amenities including a firepit and beach chairs, with access to the Cape Cod Rail Trail for biking and walking.
Chatham, MA
07/01 – 07/06
$2881/nighttotal: $14405 (5 )
Waterfront Chatham Escape, Pet Friendly, Pond Views & Beach Nearby
4 2
apartment , Chatham
This pet-friendly waterfront house in Chatham offers waterfront views of Oyster Pond, situated in a quiet neighborhood just minutes from Hardings Beach (1.9 miles) and Ridgevale Beach (2.3 miles), as well as shops and dining. This 4190 square foot residence accommodates up to 10 guests with 4 bedrooms and 5 bathrooms, featuring a fully equipped kitchen, multiple living areas including a space with a pool table, central A/C, an outdoor patio with a BBQ grill, and includes $750 worth of daily exclusive free tickets to local attractions through Xplorie.
9.0 4 reviews
Chatham, MA
08/07 – 08/14
$1920/nighttotal: $13440 (7 )
Slow M'ocean A Fresh Take On Cape Calm
3 7
apartment , Chatham
This Chatham vacation home is centrally located, a 10-minute walk from Chatham Lighthouse and Cape Cod beaches, and under a mile from Monomoy National Wildlife Refuge. This 1,540-square-foot property boasts three bedrooms, four bathrooms, sleeps eight, and includes a spa, tennis court, game room, gas grills, and on-site laundry facilities.
9.4 104 reviews
Chatham, MA
06/25 – 06/27
$679/nighttotal: $1358 (2 )
Spacious W/ Large Outdoor Area Fire Pit!
4 4
apartment , Chatham
This Chatham house is located within walking distance of popular attractions such as the Chatham Shark Center and Veterans Field. It has excellent user, location, and cleanliness ratings. The house has a floor area of 2000 square feet, 4 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features a garden, barbecue grills, a fully equipped kitchen, multiple bathrooms, a washing machine, and is pet-friendly and smoke-free. It is also situated directly by the sea, offering stunning ocean views and easy access to the beach.
8.8 39 reviews
Chatham, MA
07/15 – 07/17
$847/nighttotal: $1694 (2 )
The Spray
2 2
house , Harwich
The Spray is a vacation home located in Harwich Port, just a short walk from Bank Street Beach and a short drive from Red River Beach. The house has received very good user ratings for cleanliness and an excellent location rating. The Spray has two bedrooms and one bathroom, comfortably accommodating up to five guests. The house features a fully equipped kitchen, air conditioning, a patio, a garden, a spa, parking, and free Wi-Fi.
10 2 reviews
Chatham, MA
06/25 – 06/27
$771/nighttotal: $1542 (2 )
Cape Escape - Family-friendly Chatham Retreat
2 4
apartment , Chatham
This Chatham seaside rental is 1.5 miles from the Caleb Nickerson House and 1.6 miles from Cape Cod beaches, offering convenient access to Adventure Chatham and Ridgevale Beach within a 3-mile radius. This 1,190-square-foot vacation home features two bedrooms, two bathrooms, a fully equipped kitchen, on-site laundry, a patio, and a private spa, comfortably accommodating four guests.
Chatham, MA
07/15 – 07/17
$557/nighttotal: $1114 (2 )
Walk To Nantucket Sound Beaches! Family Getaway
3 2
house , Dennis
This vacation home in Dennis Port is a short walk to Sea Street Beach and 23 miles from Heritage Museums & Gardens and Cape Cod National Seashore. This 600-square-foot rental accommodates up to 9 guests in 3 bedrooms, featuring air conditioning, a fully equipped kitchen with a fridge and microwave, a private patio, an outdoor dining area, and free private parking.
10 1 review
Chatham, MA
08/07 – 08/14
$1567/nighttotal: $10969 (7 )
143 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 7
house , Chatham
This Chatham, Massachusetts vacation home is situated in a quiet neighborhood, just 0.5 miles from the Chatham Lighthouse and 1.3 miles from downtown Chatham, providing easy access to Lighthouse Beach and Outermost Harbor. This 1,530-square-foot house features three bedrooms with ensuite bathrooms, sleeps eight guests, and includes a fully equipped kitchen, central A/C, Wi-Fi, a wraparound deck with a firepit, and an enclosed yard perfect for pets.
10 39 reviews
Chatham, MA
07/09 – 07/13
$3229/nighttotal: $12916 (4 )
Compound On Historic Bank St Near Wychmere Club
7 6
apartment , Harwich
This three-bedroom Harwich Port cottage is located on historic Bank Street, a short walk or bike ride from Bank Street Beach, Saquatucket Harbor, and the Wychmere Beach Club. The house offers a fully equipped kitchen, laundry facilities, Wi-Fi, a grill, outdoor shower, fire pit, and sleeps up to six guests with two bedrooms upstairs and a second living area that can be used as a third bedroom; beach essentials are provided.
8.3 2767 reviews
Chatham, MA
08/04 – 08/08
$632/nighttotal: $2528 (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. The resort has excellent ratings for location, cleanliness, and overall experience. The resort offers spacious villas with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a private beach, indoor and outdoor pools, a golf course, tennis courts, a kids' club, multiple dining options, and a fitness center.
Best Chatham, MA vacation rentals with a balcony
9.6 78 reviews
Chatham, MA
08/04 – 08/08
$504/nighttotal: $2016 (4 )
Walk To Dennisport Beaches 4 Min.bars And Restaurants 2min Walk.perfect Location
1 2
apartment , Dennis
This one-bedroom apartment in Dennis is just a 10-minute walk from Sea Street Beach and Cape Cod Beaches, offering easy access to the sand and surf. It has received excellent ratings for location, cleanliness, and overall user experience. The 600 square foot apartment features a fully equipped kitchen, a private balcony, and a garden, providing a comfortable and relaxing space. You can enjoy amenities like a Smart TV with DVD player, sun loungers, and beach towels, making it perfect for a relaxing getaway.
Chatham, MA
07/15 – 07/17
$721/nighttotal: $1442 (2 )
Dog-friendly Beach Cottage On Harwich's Main Street With Large Lawn
2 2
apartment , Harwich
This Harwich Port cottage is located on the main street, two blocks from the beach and 0.5 miles from Wychmere Beach Club. This 720 square foot rental accommodates up to 5 guests with 2 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, and a terrace, with nearby green space for outdoor activities.
8.8 385 reviews
Chatham, MA
07/15 – 07/17
$968/nighttotal: $1936 (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, offering a convenient base for exploring the island and the surrounding area. The resort consistently receives high ratings for its cleanliness, location, and overall experience. The resort features comfortable rooms with walk-in showers, balconies with ocean views, and a refreshing outdoor pool. Guests can enjoy a variety of amenities, including a private beach, a restaurant, a bar, and easy access to nearby golf courses.
9.6 10 reviews
Chatham, MA
07/15 – 07/17
$1029/nighttotal: $2058 (2 )
Ideally Located Home With Yard, Grill, Bikes, Gas Fireplace, Streaming, W/d, Ac
4 2
apartment , Brewster
This spacious Brewster house is located in West Brewster, a short drive from multiple beaches and attractions such as the Cape Cod Museum of Natural History, Stony Brook Grist Mill, and Crowes Pasture Conservation Area. This 1800 sq ft residence accommodates up to 8 guests with 4 bedrooms and 4 bathrooms, featuring a fully equipped kitchen with granite countertops, central air conditioning, a private washer/dryer, a gas fireplace, and expansive outdoor space with a patio and grill, plus adult bikes for exploring the area.
Search Family Vacation Rentals in Chatham, MA
Plan the perfect family beach trip to Chatham, MA with spacious rentals that offer plenty of room to spread out.
Chatham, MA
08/07 – 08/14
$801/nighttotal: $5607 (7 )
House ∙ 4 Bedrooms ∙ 8 Guests
4 7
house , Harwich
This Harwich residence is located 1.6 miles from 400 East Restaurant and 4.8 miles from Red River Beach, offering a convenient base for exploring the area. This 4-bedroom, 2-bathroom vacation home accommodates up to 8 guests with amenities including air conditioning, a full kitchen, Wi-Fi, and a game room, plus a complimentary Linens Service and $750 in daily attraction tickets through the Xplorie partnership.
9.8 19 reviews
Chatham, MA
07/09 – 07/13
$1102/nighttotal: $4408 (4 )
Jean's Dream - Renovated Chatham House
1 6
apartment , Chatham
This South Chatham, MA vacation home is located on Main Street (Route 28), less than a mile from Cockle Cove Beach and a five-minute drive from downtown Chatham's shops and restaurants, including The Squire and Chatham Bars Inn. The newly renovated two-bedroom, one-bathroom house sleeps up to seven guests, features an open-concept living/dining/kitchen area, a private backyard with a grill and outdoor shower, and offers direct access to the Cape Cod Rail Trail.
9.6 8 reviews
Chatham, MA
07/15 – 07/17
$832/nighttotal: $1664 (2 )
Gray Gables | House In Orleans
4 2
apartment , Orleans
This historic East Orleans residence offers a secluded retreat on over an acre, with direct access to 33 acres of conservation land, a short walk to Nauset Inlet, and beaches and downtown Orleans within two miles. This 1880 sq ft rental comfortably accommodates six guests with four bedrooms and three bathrooms, featuring a full kitchen with updated appliances, air conditioning, and outdoor space with yard games and a dining deck.
9.3 84 reviews
Chatham, MA
08/04 – 08/08
$583/nighttotal: $2332 (4 )
Captain Alexanders Spa & Putting Green Not A Vacation Home But A Destination.
2 2
apartment , Harwich
This Harwich vacation rental is conveniently located just a 10-minute walk from Cape Cod Beaches and Earle Road Beach, offering easy access to the beautiful coastline. Guests consistently rate this property as excellent, highlighting its comfortable accommodations and convenient amenities. This home features a private fenced yard, perfect for relaxing and enjoying the outdoors. Enjoy the spa tub, barbecue grills, fully equipped kitchen, free Wi-Fi, and a quiet location near the beach.
Frequently Asked Questions about vacation rentals in Chatham, MA
Which walking or cycling routes are the best in Chatham, MA?
The Chatham Rail Trail is a great place to walk or bike, and it's a paved path, so it's easy to push a stroller or ride a bike. You can also walk or bike along the Chatham Lighthouse Beach, which is a beautiful stretch of beach with views of the ocean. The Chatham Bars Inn also has a nice walking path along the water.
What are the best Airbnb and vacation rentals in Chatham, MA?
What sports or outdoor activites can visitors enjoy in and around Chatham, MA?
Chatham is a great place for water sports. You can go swimming, surfing, kayaking, or paddleboarding. There are also a number of golf courses in the area. If you're looking for something more active, you can go hiking or biking in the Cape Cod National Seashore.
What other towns or cities can be easily accessed from Chatham, MA?
You can easily get to other towns on Cape Cod from Chatham. Orleans, Harwich, and Dennis are all within a 15-minute drive. You can also take the ferry to Nantucket, which is a beautiful island with lots of shops and restaurants.
What are the best vacation rentals with a pool in Chatham, MA?
What amenities are commonly available in vacation rentals in Chatham, MA?
Vacation rentals in Chatham usually include amenities like a kitchen, a living room, a dining area, and bedrooms. Many also have a deck or patio, and some even have a pool. Be sure to check the listing carefully to see what amenities are included.
What are the best rentals for families and kids in Chatham, MA?
What time of year is best to rent a vacation rental Chatham, MA?
The best time to visit Chatham is during the summer, when the weather is warm and sunny. However, if you're looking for a more relaxing and less crowded experience, you can visit in the spring or fall. The shoulder seasons are also a good time to visit because you can often find better deals on vacation rentals.
What are the best rentals or Airbnbs with a jacuzzi in Chatham, MA?
This Harwich Port cottage, a six-minute walk from Bank Street Beach and twelve miles from Cape Cod Gateway Airport, offers easy access to Harwich's attractions. This 1,290-square-foot house features one bedroom, two bathrooms, accommodates seven guests, and includes a fully equipped kitchen, private parking, Wi-Fi, and a garden.
Chatham, MA
08/04 – 08/08
$533/nighttotal: $2132 (4 )
New For 2026! 1/2 Mile To Swan Pond (2414)
2 2
cottage , Dennis
This Dennis Port seaside cottage offers stunning ocean views and is an 8-minute drive from both Cape Cod Beaches and Sea Street Beach. The 820-square-foot house features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, Wi-Fi, air conditioning, a garden, and parking.
Chatham, MA
07/09 – 07/13
$831/nighttotal: $3324 (4 )
Dog-friendly Pleasant Lake Cottage In Harwich
3 6
apartment , Harwich
This Harwich cottage is located less than 0.25 miles from the Cape Cod Rail Trail and within a 0.5 mile walk to Long Pond, Hinckley's Pond, and Seymour's Pond, with local eateries and a general store accessible by bike or foot. This 1650 square foot rental sleeps up to 6 guests and features 3 bedrooms, 1 bathroom, a three-season porch, gas grill, and includes complimentary linens and $750 worth of daily exclusive free tickets to local attractions through the Xplorie partnership.
9.0 2 reviews
Chatham, MA
07/09 – 07/13
$1032/nighttotal: $4128 (4 )
Stylish Cape Escape On Bank St Rpam070
3 6
apartment , Harwich
This restored antique home is located in downtown Harwich, a short walk from Brooks Park and the Cape Cod Rail Trail Bike Path, and 5 miles from Hyannis Harbor. This 3-bedroom, 2-bathroom rental offers 1740 square feet of living space for up to 6 guests, featuring a fully equipped kitchen, air conditioning, a garden with an outdoor fireplace, and parking.
Check Out Vacation Rentals with a Pool in Chatham, MA
Complement your time by the water with a dip in the pool at these Chatham, MA vacation rentals with on-site swimming facilities.
9.6 5 reviews
Chatham, MA
08/07 – 08/14
$897/nighttotal: $6279 (7 )
House ∙ 3 Bedrooms ∙ 8 Guests
3 7
house , Chatham
Azure Cottage, located in Chatham's Oyster Pond area, is less than a mile from downtown Chatham and 1.2 miles from Oyster Pond. This three-bedroom, two-bathroom Cape Cod-style home sleeps eight, boasts a private 3/4-acre lot with a pool, hot tub, and outdoor amenities, plus includes a $750 Xplorie package for local attractions.
9.3 348 reviews
Chatham, MA
07/01 – 07/06
$2382/nighttotal: $11910 (5 )
Wequassett Resort And Golf Club
1 2
resort , Harwich
The Wequassett Resort And Golf Club is located in Harwich, a short drive from the town center and the Cape Cod National Golf Center. This resort has received excellent ratings for its location, user experience, and cleanliness. The resort has spacious rooms with sitting areas and private decks or patios. Guests can enjoy a variety of amenities, including a swimming pool, hot tub, tennis court, fitness center, and restaurant, as well as a golf course and spa.
10 1 review
Chatham, MA
06/25 – 06/27
$1284/nighttotal: $2568 (2 )
Chatham On A Whim!
1 4
apartment , Chatham
This four-bedroom Chatham home is located 1.5 miles from Ridgevale Beach, offering easy access to Chatham's coastal attractions. The house features a spacious layout, accommodating eight guests with two bathrooms, a private above-ground pool, hot tub, and a fully fenced yard; new furniture and central air conditioning are included.
9.2 37 reviews
Chatham, MA
07/15 – 07/17
$822/nighttotal: $1644 (2 )
Charming Second-floor Retreat With A Full Kitchen And Balcony View
2 2
apartment , Brewster
This two-bedroom condo in Brewster is located within the Ocean Edge Resort Golf Course, 1.4 miles from Ellis Landing Beach and a short drive to Provincetown and the National Seashore. This family-friendly 950 sq ft unit accommodates up to six guests with two bathrooms, an open-concept living space, and access to resort amenities including pools and a fitness center with a paid amenities pass.
Browse Waterfront Vacation Rentals in Chatham, MA
Discover beautiful beach towns with these seaside vacation rentals in Chatham, MA, perfect for relaxing near the coast and exploring the shore.
Chatham, MA
08/07 – 08/14
$1987/nighttotal: $13909 (7 )
Slow M'ocean – A Fresh Take On Cape Calm
1 7
house , Chatham
Chatham, MA
07/01 – 07/06
$827/nighttotal: $4135 (5 )
Lighthouse Flat-ocean Views-walk To Chatham Center
1 2
apartment , Chatham
Chatham, MA
08/07 – 08/14
$2562/nighttotal: $17934 (7 )
Spacious 5-bedroom Oceanfront Estate In Marvelous Chatham With Ac
5 7
apartment , Chatham
Chatham, MA
08/04 – 08/08
$566/nighttotal: $2264 (4 )
Serene Retreat With Cove Views
1 2
house , Eastham
Compare Luxury Vacation Rentals in Chatham, MA
Discover the best of the coast with a luxury vacation rental in Chatham, MA, offering sophisticated rooms and prime locations.
9.8 297 reviews
Chatham, MA
07/15 – 07/17
$286/nighttotal: $572 (2 )
The Secret Garden
1 2
apartment , Harwich
Discover Vacation Rentals with Saunas in Chatham, MA
Maximize your wellness with vacation rentals in Chatham, MA featuring on-site saunas and steam rooms.