Best Holiday rentals and Airbnb offers in Chatham, MA
10 70 reviews
Chatham, MA
09/07 – 13/07
£920/nighttotal: £3680 (4 )
Luxury New Spacious Modern Cape Cod Home
1 6
apartment , Harwich
This luxurious Harwich house, near Chatham (a 5-8 minute, or approximately 8-13 kilometre, drive away), offers easy access to local attractions. This spacious 229 sq m property boasts a 4-bedroom, 2-bathroom layout sleeping up to 10 guests, complete with a fully equipped kitchen, game room, garden, fitness centre, and ample parking.
9.0 4 reviews
Chatham, MA
07/08 – 14/08
£1433/nighttotal: £10031 (7 )
Slow M'ocean A Fresh Take On Cape Calm
3 7
apartment , Chatham
This Chatham holiday home is centrally located, less than 1.6km from Chatham Lighthouse and Cape Cod beaches, and under 1.6km from Monomoy National Wildlife Refuge. The 143 square metre property boasts three bedrooms, four bathrooms, sleeps eight guests, and includes a spa, tennis court, and on-site games room.
10 12 reviews
Chatham, MA
15/08 – 22/08
£2169/nighttotal: £15183 (7 )
Walk 2beach, Pool, Hot Tub, Gameroom, Petsok
4 10
apartment , Chatham
This four-bedroom apartment in Chatham is situated just a short walk from Hardings Beach, offering easy access to the beautiful coastline. The 334.45 square metre property boasts a private pool and hot tub, a game room, a movie room, and an outdoor kitchen with a fire pit area, providing ample space and entertainment options for up to 10 guests.
10 3 reviews
Chatham, MA
15/08 – 22/08
£924/nighttotal: £6468 (7 )
Dogs Welcome, Huge Yard Right Next To Rail Trail!
4 10
apartment , Harwich
This Harwich holiday home is ideally situated, approximately 2.4 kilometres from Red River Beach and Cape Cod Beaches, and within 3.2 kilometres of Harwich Port and Forest Beach. This five-bedroom property boasts 222 square metres of floor space, two and a half bathrooms, sleeps ten guests, and includes a fully equipped kitchen, terrace, garden, fireplace, and Wi-Fi.
9.0 2 reviews
Chatham, MA
07/08 – 14/08
£734/nighttotal: £5138 (7 )
Azure Cottage: Central A/c & Hot Tub
3 7
apartment , Chatham
Azure Cottage, situated in Chatham's Oyster Pond area, is less than 1.6km from Chatham town centre and 1.9km from Oyster Pond, offering easy access to shops, restaurants and the town landing. This three-bedroom, two-bathroom holiday home sleeps eight, boasting a well-equipped kitchen, jacuzzi, fitness centre, private garden, and finished basement with sitting area; one dog is permitted for a nightly fee.
Chatham, MA
04/08 – 08/08
£404/nighttotal: £1616 (4 )
Serene Retreat With Cove Views
1 2
cottage , Eastham
This waterfront bungalow in Eastham offers direct access to Town Cove, featuring a private dock ideal for launching kayaks and canoes, and is conveniently located within 5 kilometres of the Cape Cod National Seashore, bay and ocean beaches, and local amenities. This dog-friendly property boasts a 60 square meter open-plan interior for two guests, with air conditioning, Wi-Fi, a kitchen equipped with a fridge and microwave, and includes daily $750 worth of tickets to local attractions via the Xplorie partnership.
Chatham, MA
04/08 – 08/08
£671/nighttotal: £2684 (4 )
Ranch-style Retreat By Leavetown Vacations
3 2
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.
10 2 reviews
Chatham, MA
15/08 – 22/08
£796/nighttotal: £5572 (7 )
Peace, Patio And Paws!
4 10
apartment , Chatham
This Chatham holiday home, situated on a quiet cul-de-sac less than 1.6km from Ridgevale Beach and 0.8km from the Cape Cod Rail Trail, offers convenient access to Chatham's attractions. Sleeping up to 10 guests in four bedrooms and two bathrooms, this spacious property includes a well-equipped kitchen, a deck, patio, screened porch, and outdoor shower; nearby activities include swimming, biking, and attending Cape Cod Baseball League games.
9.3 348 reviews
Chatham, MA
09/07 – 13/07
£3134/nighttotal: £12536 (4 )
Wequassett Resort And Golf Club
2 6
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.
Chatham, MA
01/07 – 06/07
£613/nighttotal: £3065 (5 )
Beautiful Harwich Home
3 2
apartment , Harwich
This Cape-style property in Harwich is located a short distance from Red River Beach and is minutes from Harwich Port's shops and restaurants. This three-bedroom, one-bathroom flat accommodates six guests and features a private garden with a patio, outdoor shower, and barbecue, plus central air conditioning and high-speed internet.
Chatham, MA
07/08 – 14/08
£598/nighttotal: £4186 (7 )
House ∙ 4 Bedrooms ∙ 8 Guests
4 7
house , Harwich
This detached house in Harwich is located 8 kilometres from Red River Beach and 7.9 kilometres from Nickerson State Park, offering convenient access to local dining and golf. This family-friendly property accommodates up to eight guests with four bedrooms, two bathrooms, air conditioning, Wi-Fi, a fully equipped kitchen, and features an outdoor shower, a fire pit, a garage game room with ping pong, air hockey and cornhole, and includes a complimentary linens service and $750 worth of daily free tickets to local attractions via the Xplorie partnership.
Chatham, MA
09/07 – 13/07
£696/nighttotal: £2784 (4 )
Stylish Harwich Home With Amazing Outdoor Space
1 6
apartment , Harwich
This Harwich holiday home, a beautifully restored antique property, is centrally located in downtown Harwich, within walking distance of Brooks Park and the Cape Cod Rail Trail. The three-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped chef's kitchen, air conditioning, a garden with patio and outdoor shower, plus streaming TVs and is close to shops and restaurants.
Best family friendly Chatham, MA holiday rentals
Among the 1015 accommodations in Chatham, MA, here are the 4 best family friendly rentals
9.3 84 reviews
Chatham, MA
04/08 – 08/08
£435/nighttotal: £1740 (4 )
Captain Alexanders Spa & Putting Green Not A Vacation Home But A Destination.
2 2
apartment , Harwich
This Harwich property is just a short walk from Cape Cod Beaches and Earle Road Beach, offering a peaceful escape from the hustle and bustle of town. The house has received excellent guest ratings, making it a popular choice for travellers. This three-bedroom holiday home provides ample space for families or groups. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, a swimming pool, a Jacuzzi and a spa, as well as free Wi-Fi access.
8.6 4 reviews
Chatham, MA
15/08 – 22/08
£840/nighttotal: £5880 (7 )
Posh Pad With King Beds Central A/c
4 10
cottage , Harwich
This 4-bedroom Cape Cod holiday home is located on a quiet, tree-lined street in Harwich, a short drive from Cape Cod Beaches and Mayflower Beach, and convenient to Adventure Chatham and Cape Cod Lavender Farm. This 130 square meter property accommodates up to 12 guests and features central air conditioning, a fully equipped kitchen, a fireplace, an outdoor shower, and is ideal for water activities and hiking.
8.6 7 reviews
Chatham, MA
04/08 – 08/08
£313/nighttotal: £1252 (4 )
Captain's Quarters @ Captain Alexander's Hideaway 5 Minute Walk To The Beach
1 2
apartment , Harwich
This cosy apartment is located in West Harwich, just a short walk from Earle Road Beach and a mile from the charming village of Harwichport. It has been consistently rated very good by previous guests. The apartment is compact, measuring just 14 square metres, but is equipped with everything you need for a comfortable stay. You can enjoy the private yard with an outdoor shower, a gas grill, and a table and chairs, and stay connected with high-speed internet.
This five-bedroom property is located on the beach side of Route 28 in South Harwich, just over a mile from Red River Beach and a short distance from Chatham. The house has received excellent user ratings, reflecting its high standard of comfort and convenience. The spacious house, spanning 251 square metres, comfortably accommodates up to 10 guests. Amenities include a fully equipped kitchen, a basement game room, a fenced backyard with a patio and fire pit, and central air conditioning.
Compare Self-Catering Holiday Rentals with a Swimming Pool in Chatham, MA
A holiday rental or Airbnb with a swimming pool near the water in Chatham, MA is a brilliant base for a relaxing swim. View our collection.
10 4 reviews
Chatham, MA
15/08 – 22/08
£1945/nighttotal: £13615 (7 )
Breathtaking Harwich Retreat W/ Heated Pool And Spa Rpam086
4 10
apartment , Harwich
This Harwich holiday home, near Red River Beach (1.9 km) and Bank Street Beach (3 km), offers easy access to Harwich Port (2.9 km) and Chatham (7.7 km). The 339-square-metre property boasts four bedrooms, four bathrooms, sleeps up to sixteen guests, and includes a 20x40ft heated swimming pool, hot tub, and fully equipped gourmet kitchen.
9.5 48 reviews
Chatham, MA
15/08 – 22/08
£2365/nighttotal: £16555 (7 )
Heated Pool Ac 1/2 Mile To Beach!
8 10
apartment , Harwich
This South Harwich holiday home boasts an excellent location, less than 1.6km from Red River Beach and Cape Cod Beaches, and within 3.2km of Forest Beach and Harwich Port. This eight-bedroom property offers 278 square metres of space, including a private pool, fully equipped kitchen, laundry facilities, and parking, perfect for large families or groups seeking a relaxing seaside escape.
9.8 41 reviews
Chatham, MA
15/08 – 22/08
£1885/nighttotal: £13195 (7 )
Walk 2beach, Pool, Hot Tub, Gameroom, Petsok
1 10
apartment , Chatham
This stunning four-bedroom Chatham holiday home is situated near Hardings Beach, a short walk from the shore and close to paddleboard rentals and walking trails. The property boasts four bathrooms, a private pool and hot tub, a fully equipped outdoor kitchen, an indoor game room, a movie room, and a fire pit, comfortably accommodating up to ten guests.
Chatham, MA
15/08 – 22/08
£3150/nighttotal: £22050 (7 )
Have It All! Beach, Town, & Pool
1 10
apartment , Chatham
This Chatham estate, near the headwaters of Upper Mill Pond and Mitchell River, is within walking distance of Chatham's town centre and Lighthouse Beach. Sleeping up to 16 guests, this seven-bedroom, six-bathroom property comprises a main house and guest cottage, boasting a swimming pool, fitness centre, and ample parking, ideal for large family gatherings or multi-family holidays.
Frequently asked questions about holiday rentals in Chatham, MA
Which walking or cycling routes are the best in Chatham, MA?
Chatham has many beautiful walking and cycling routes. The Chatham Coastal Trail is a great option for a scenic walk or bike ride. It follows the coastline and offers stunning views of the ocean. If you're looking for a shorter walk, the Chatham Light Beach Trail is a nice option, leading to the Chatham Lighthouse.
What are the best Airbnb and 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 swimming, sunbathing, or surfing at one of the many beaches. You can also go kayaking, paddleboarding, or windsurfing in the harbour. There are also plenty of opportunities for hiking and biking in the surrounding area.
What other towns or cities can be easily accessed from Chatham, MA?
Chatham is well-connected to other towns and cities on Cape Cod. You can easily drive to nearby towns like Harwich Port, Dennis Port, and Orleans. If you want to explore further afield, you can take a ferry to Nantucket or Martha's Vineyard.
What are the best holiday rentals with a pool in Chatham, MA?
What amenities are commonly available in vacation rentals in Chatham, MA?
Vacation rentals in Chatham typically offer a range of amenities, including kitchens, bathrooms, bedrooms, living rooms, and outdoor spaces. Many rentals also have access to swimming pools, hot tubs, and other recreational facilities.
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 rent a vacation rental in Chatham depends on your preferences. Summer is the most popular time to visit, but it can be crowded and expensive. Spring and autumn offer more moderate temperatures and fewer crowds. Winter can be a great time to visit if you enjoy the peace and quiet.
What are the best rentals or Airbnbs with a jacuzzi in Chatham, MA?
Chatham's local cuisine is heavily influenced by its proximity to the ocean. You can find fresh seafood dishes like lobster rolls, clam chowder, and fish and chips. There are also many restaurants that serve traditional New England dishes like clam bake and Yankee pot roast.
Destinations nearby
Best Chatham, MA holiday rentals with a balcony
10 1 review
Chatham, MA
15/08 – 22/08
£644/nighttotal: £4508 (7 )
Waterfront Home With Lovely Lake Views, Great Deck, Sun Porch & Fireplace
3 10
apartment , Chatham
This waterfront property in South Chatham offers direct access to Mill Pond with scenic views, and is located 6 kilometres east of downtown Chatham, 1.6 kilometres from Hawksnest State Park, 3.2 kilometres from the Old Colony Rail Trail, and 4.8 kilometres from Forest Beach and Ridgevale Beach. This spacious 193 square metre residence, ideal for up to 10 guests, features an open layout, a sun porch, an eat-in kitchen, a living room with a 60-inch HDTV, three bedrooms, central air conditioning, a washer/dryer, complimentary WiFi, and a lake-facing deck with a gas grill.
9.6 78 reviews
Chatham, MA
04/08 – 08/08
£376/nighttotal: £1504 (4 )
Walk To Dennisport Beaches 4 Min.bars And Restaurants 2min Walk.perfect Location
1 2
apartment , Dennis
This apartment is located near the beach in Dennis, within a 10-minute walk of Sea Street Beach and Cape Cod Beaches, and within 2 miles of the Cape Cod Theatre Company and Swan Pond River. The property has received excellent ratings for user experience, location, and cleanliness. The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square meters. Guests can enjoy a fully equipped kitchen, internet access, and a terrace or balcony, as well as parking, a garden, and a range of other amenities.
9.9 91 reviews
Chatham, MA
15/08 – 22/08
£1314/nighttotal: £9198 (7 )
Beautifully Renovated W/ Access To Beach!
6 10
apartment , Chatham
This Chatham house is located just a 2.4 kilometre walk from the Chatham Shark Center and Cape Cod Beaches, and a 3.2 kilometre drive from Fox Hill and Chatham Fish Pier, making it a great base for exploring the area. The property has excellent user, location and cleanliness ratings. The house has 4 bathrooms and is 325 square metres in size. It features a fully equipped kitchen, garden, terrace, air conditioning, parking and free Wi-Fi, as well as a washing machine, coffee/tea maker, and a TV.
8.3 2671 reviews
Chatham, MA
04/08 – 08/08
£472/nighttotal: £1888 (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.
Top-Rated Self-Catering Holiday Rentals with Free Parking in Chatham, MA
Parking is sorted from the start as these holiday rentals near the water in Chatham, MA include free on-site spaces.
8.9 56 reviews
Chatham, MA
04/08 – 08/08
£501/nighttotal: £2004 (4 )
Inn On The Beach
1 2
resort , Harwich
The Inn On The Beach is located in Harwich Port, a 32km drive from Nickerson State Park, offering a peaceful escape on the Cape Cod coast. The property receives consistently high ratings for its cleanliness, location, and overall experience. The hotel offers a range of comfortable rooms with amenities like a microwave, refrigerator, patio, and cable TV. Guests can enjoy a continental breakfast, free Wi-Fi, and direct access to a private beach with lounge chairs, hammocks, and beach umbrellas.
This five-bedroom, three-bathroom detached house in Brewster offers immediate access to the Cape Cod Rail Trail, Nickerson State Park, and Blueberry Pond, with bay beaches such as Breakwater Beach and Paine's Creek just minutes away. This property boasts a spacious 0.7-acre private garden with a fire pit and Adirondack chairs, a jacuzzi tub in the master en-suite, an outdoor shower, and an open-plan upper-level living, dining, and kitchen space with vaulted ceilings and a gas fireplace, accommodating up to six guests.
Chatham, MA
07/08 – 14/08
£765/nighttotal: £5355 (7 )
Driftwood - Har - Ed13
1 7
house , Harwich
This Harwich holiday cottage offers a convenient base, situated 21-24 kilometres from Nauset Lighthouse and the Cape Cod National Seashore, with Wellfleet Bay Wildlife Sanctuary also 22 kilometres away. This property accommodates up to 15 guests across 4 bedrooms and features a fully equipped kitchen with a dishwasher and oven, air conditioning, private parking, and complimentary WiFi, ideal for exploring the Cape.
Chatham, MA
04/08 – 08/08
£3654/nighttotal: £14616 (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.