Best Holiday rentals and Airbnb offers in Chatham, MA
10 3 reviews
Chatham, MA
25/06 – 27/06
£700/nighttotal: £1400 (2 )
Peaceful Beach Retreat: Private Yard, Close To Beaches, Chatham & Rail Trail
2 4
apartment , Harwich
This Harwich flat is located on a tranquil residential street bordering conservation land, a 5 to 10-minute drive from Red River and Bank Street beaches, and within easy reach of Harwich and Chatham Centres for amenities. This family-friendly maisonette offers 139 square meters of living space for up to 4 guests, featuring 2 bedrooms, 1 bathroom, central air conditioning, WiFi, a kitchen with a fridge, microwave, and dishwasher, a game room with ping-pong, and a patio with a firepit, with the Cape Cod Rail Trail nearby for outdoor pursuits.
9.4 32 reviews
Chatham, MA
04/08 – 08/08
£347/nighttotal: £1388 (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.
9.2 37 reviews
Chatham, MA
15/07 – 17/07
£613/nighttotal: £1226 (2 )
Charming Second-floor Retreat With A Full Kitchen And Balcony View
2 2
apartment , Brewster
This apartment is situated within the historic town of Brewster, offering a prime location on Cape Cod, 2.3 kilometres from Ellis Landing Beach and 29 kilometres from the National Seashore, with Provincetown 51 kilometres away. This 88-square-metre flat features two bedrooms and two bathrooms, accommodating up to six guests with an open-concept living and kitchen area, air conditioning, a swimming pool, and access to resort amenities.
9.0 1 review
Chatham, MA
04/08 – 08/08
£388/nighttotal: £1552 (4 )
Beachside Retreat! Cozy 1-bedroom W Private Yard
1 2
house , Dennis
This Dennis, Massachusetts beachfront property is a three-minute walk from Sea Street Beach and 2.1 kilometres from South Village Beach, with Nauset Lighthouse and Wellfleet Bay Wildlife Sanctuary approximately 32 kilometres away. This self-catering cottage offers 56 square metres of accommodation, sleeping up to three guests in one bedroom and one bathroom, with amenities including free Wi-Fi, private parking, and a fully equipped kitchen.
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.
Chatham, MA
03/07 – 11/07
£899/nighttotal: £7192 (8 )
Seaside Cottage
1 4
apartment , Chatham
This seaside cottage in the Ridgevale district is just 250 meters from Ridgevale Beach, offering a seaside experience with easy access to ocean breezes and beach activities. This property accommodates up to six guests across three bedrooms on the main floor, featuring central air conditioning, a kitchen with a dishwasher, an outdoor shower, and a private garden with a grill and firepit, all a short drive from town attractions.
Chatham, MA
01/07 – 06/07
£617/nighttotal: £3085 (5 )
Lighthouse Flat-ocean Views-walk To Chatham Center
1 2
apartment , Chatham
This newly renovated upstairs flat in Chatham offers direct ocean views and is located directly opposite a Cape Cod beach, a short walk from Chatham centre's shops and restaurants, and adjacent to Chatham Light. This one-bedroom flat accommodates up to four guests and features air conditioning, internet, a kitchen, parking, and access to a private roof deck.
8.6 18 reviews
Chatham, MA
04/08 – 08/08
£580/nighttotal: £2320 (4 )
Sunrise And Sunset From Private Beach In Dennis Port! (2132)
2 2
apartment , Dennis
This Dennis Port waterfront flat, approximately 0.03km from Nantucket Sound and a short distance from Old Wharf Village's private beach, offers easy access to the mid-Cape's attractions. The two-bedroom, two-bathroom apartment sleeps four, boasts a well-equipped kitchen including a dishwasher, air conditioning throughout, parking for two cars, and enjoys excellent guest reviews.
9.0 44 reviews
Chatham, MA
15/07 – 17/07
£394/nighttotal: £788 (2 )
"Chatham Up”
2 2
apartment , Chatham
This charming holiday home is located in a peaceful neighbourhood in North Chatham, just a short walk from Veteran's Field and a little over 1.6km from Oyster Pond. The property has received excellent ratings for location, cleanliness, and overall quality, making it a popular choice for travellers. The spacious property spans 111 square metres and comfortably accommodates up to 5 guests in its two bedrooms and one bathroom. It features a well-equipped kitchen, a private garden, a spa, and a range of modern amenities for a relaxing and enjoyable stay.
9.9 40 reviews
Chatham, MA
25/06 – 27/06
£931/nighttotal: £1862 (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.
Chatham, MA
15/07 – 17/07
£538/nighttotal: £1076 (2 )
Dog-friendly Beach Cottage On Harwich's Main Street With Large Lawn
2 2
apartment , Harwich
This apartment is located on Harwich's main street, 500 metres from the beach and 800 metres from Wychmere Beach Club, offering convenient access to amenities and local attractions. This 67 square metre flat accommodates up to five guests in two bedrooms and one bathroom, featuring a full kitchen (no dishwasher), air conditioning, and a terrace, with a nearby garden area for outdoor activities.
Chatham, MA
04/08 – 08/08
£727/nighttotal: £2908 (4 )
Harwich Escape – Deck, Firepit & Near Beaches
3 2
apartment , Harwich
This Harwich Port flat is situated 0.7 kilometres from Pleasant Road beach, with Harwich Port's shops and eateries a short distance away, and offers convenient access to the Cape Cod Rail Trail for cycling and walking. This property accommodates up to eight guests across three bedrooms and two bathrooms, boasting a garden with a deck, patio, gas grill and firepit, an outdoor shower, and a well-equipped kitchen with full-size appliances, plus air conditioning and Wi-Fi for comfort.
Browse Waterfront Holiday Rentals in Chatham, MA
Experience relaxing coastal vibes at seaside holiday rentals in Chatham, MA, positioned short distances from local beach-town shorelines.
9.1 1099 reviews
Chatham, MA
04/08 – 08/08
£1320/nighttotal: £5280 (4 )
Chatham Bars Inn
1 2
resort , Chatham
Chatham Bars Inn is an oceanfront hotel in Chatham, Massachusetts, a short distance from the Chatham Lighthouse and the Chatham Bars. The hotel consistently receives excellent ratings for its location, user experience, and cleanliness. The hotel offers a range of rooms and suites, all featuring modern amenities. Guests can enjoy a variety of on-site amenities and activities, including a heated pool, private beach access, a full-service spa, and several restaurants.
9.4 20 reviews
Chatham, MA
04/08 – 08/08
£1196/nighttotal: £4784 (4 )
Barley Breeze
3 2
house , Orleans
This East Orleans holiday home is situated approximately 4.2 km from Cape Cod beaches and 4.7 km from Nauset Inlet, offering easy access to coastal attractions and the Orleans Bowling Centre. The 187 square metre property boasts three bedrooms, three bathrooms, and sleeps eight, featuring a fully equipped kitchen, garden, terrace, and parking; nearby activities include Nauset Beach (within 9.7 km).
Chatham, MA
02/07 – 11/07
£1510/nighttotal: £13590 (9 )
Fantastic Ocean Views, Steps To Shared Private Beach!
4 4
apartment , Dennis
This spacious coastal residence in Dennis Port provides views of Nantucket Sound and is a short walk to acclaimed eateries such as Pelham House and Ocean House, situated approximately 1.6 kilometres from Cape Cod Beaches and Mayflower Beach. This 182 square metre apartment offers accommodation for up to 10 guests across four bedrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning in each bedroom, and an outdoor dining area perfect for enjoying the coastal atmosphere and nearby water sports.
Chatham, MA
03/07 – 11/07
£678/nighttotal: £5424 (8 )
Coral Sunsets And Cool Ocean Breezes!
2 4
apartment , Chatham
This two-bedroom, three-bathroom holiday cottage, ideal for up to six guests, is situated on Lobster Lane in Chatham, a short 100-metre walk from Little Beach and a convenient cycle ride from the village's shops and ice cream parlours. Guests can enjoy complimentary Wi-Fi, air conditioning in each bedroom, a private back deck for sunset views, and outdoor barbecue facilities, with two queen bedrooms upstairs and two twin beds in the downstairs den.
Best family friendly Chatham, MA holiday rentals
Among the 1015 accommodations in Chatham, MA, here are the 4 best family friendly rentals
9.6 42 reviews
Chatham, MA
15/07 – 17/07
£639/nighttotal: £1278 (2 )
Chatham - Avail 6/14-19, 21- 25! Walk To Beaches!
1 2
apartment , Chatham
This Chatham holiday home is situated less than 1 km from Nantucket Sound beaches, 0.8 km from shops and restaurants, and a short drive from Forest Beach, Pleasant Street Beach, and Schoolhouse Pond. The 186-square-metre property boasts two bathrooms (one with a Jacuzzi), a private garden with a deck and patio, sleeps five guests, and includes a fully equipped kitchen, laundry facilities, and a cornhole game.
8.3 2767 reviews
Chatham, MA
25/06 – 27/06
£459/nighttotal: £918 (2 )
The Mansion At Ocean Edge Resort & Golf Club
1 4
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.
9.3 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.
9.8 19 reviews
Chatham, MA
09/07 – 13/07
£822/nighttotal: £3288 (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.
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
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.
9.0 44 reviews
Chatham, MA
15/07 – 17/07
£703/nighttotal: £1406 (2 )
Charming Second-floor Retreat With A Full Kitchen And Balcony View
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.
10 1 review
Chatham, MA
25/06 – 27/06
£958/nighttotal: £1916 (2 )
Chatham On A Whim!
1 4
apartment , Chatham
This four-bedroom house in Chatham is situated 2.4 kilometres from Ridgevale Beach. The property boasts a spacious layout, sleeping eight guests, with a private pool, hot tub, and fully fenced yard; it also includes a fully equipped kitchen and central air conditioning.
9.3 348 reviews
Chatham, MA
02/07 – 11/07
£1825/nighttotal: £16425 (9 )
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.
10 6 reviews
Chatham, MA
15/07 – 17/07
£267/nighttotal: £534 (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.
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.
10 1 review
Chatham, MA
04/08 – 08/08
£510/nighttotal: £2040 (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.
9.6 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.
10 14 reviews
Chatham, MA
15/07 – 17/07
£2225/nighttotal: £4450 (2 )
Beautiful Home In Orleans. Park, Beach, Lake & Ocean. Telsa Charge
7 2
apartment , Orleans
This seven-bedroom house is located on a river in Orleans, just 0.16 kilometers from Nickerson State Park and within 5 kilometers of Orleans Bowling Center, Stony Brook Grist Mill, Skaket Beach, and Jonathan Young Windmill. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests. The house comfortably accommodates up to 26 guests and features a fully equipped kitchen, a garden, barbecue grills, and a terrace. Guests can enjoy stunning river views, relax in the tranquil surroundings, and explore the diverse ecosystem of Nickerson State Park, all within easy reach of Orleans' attractions and activities.
9.8 76 reviews
Chatham, MA
03/07 – 11/07
£498/nighttotal: £3984 (8 )
Chatham Village - Lovely 2 Bedroom Apartment In The Antique Home
2 4
apartment , Chatham
This Chatham apartment, centrally located less than 1.6km from Mayo House and Cape Cod beaches, offers easy access to Chatham Windmill and Monomoy Theatre within a 24km radius. The two-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen, private patio, fireplace, and free Wi-Fi; a spa and parking are also available.
Handpicked Luxury Holiday Rentals in Chatham, MA
Upscale luxury holiday rental or Airbnbs in Chatham, MA offer a refined stay you will want to return to, featuring premium amenities throughout.
Chatham, MA
02/07 – 11/07
£514/nighttotal: £4626 (9 )
Charming Dog Friendly North Chatham Ranch
2 4
house , Chatham
Best Chatham, MA holiday rentals with a balcony
Chatham, MA
15/07 – 17/07
£416/nighttotal: £832 (2 )
Walk To Nantucket Sound Beaches! Family Getaway
3 2
house , Dennis
9.8 53 reviews
Chatham, MA
15/07 – 17/07
£553/nighttotal: £1106 (2 )
Classic Home With Deck, Patio & Yard - Walk To Cockle Cove & Forest Beaches
3 2
apartment , Chatham
8.9 56 reviews
Chatham, MA
04/08 – 08/08
£501/nighttotal: £2004 (4 )
Inn On The Beach
1 2
resort , Harwich
9.6 10 reviews
Chatham, MA
15/07 – 17/07
£768/nighttotal: £1536 (2 )
Ideally Located Home With Yard, Grill, Bikes, Gas Fireplace, Streaming, W/d, Ac
4 2
apartment , Brewster
Explore Pet-Friendly Holiday Rentals in Chatham, MA
These dog-friendly holiday rentals and Airbnbs in Chatham, MA guarantee a holiday your pet will enjoy as much as you.
Chatham, MA
25/06 – 27/06
£721/nighttotal: £1442 (2 )
Harwich Coastal Cottage: Cape Gem In Harwich Port
3 4
apartment , Harwich
Chatham, MA
25/06 – 27/06
£534/nighttotal: £1068 (2 )
Harwich Getaway By Leavetown Vacations
3 4
house , Harwich
10 1 review
Chatham, MA
25/06 – 27/06
£694/nighttotal: £1388 (2 )
Harwich Coastal Cottage Cape Gem In Harwich Port
3 4
house , Harwich
Chatham, MA
04/08 – 08/08
£422/nighttotal: £1688 (4 )
450 State Highway Eastham - Top Deck
1 2
house , Eastham
Choose the Right Holiday Rentals with a Hot Tub in Chatham, MA
These holiday rentals near the water in Chatham, MA come with a hot tub or jacuzzi, ideal for a private evening soak. Explore now.
Chatham, MA
04/08 – 08/08
£3654/nighttotal: £14616 (4 )
Dennis Family Oasis: Pool, Hot Tub, & Fire Pit!
1 2
apartment , Dennis
9.6 458 reviews
Chatham, MA
25/06 – 27/06
£386/nighttotal: £772 (2 )
Front Deluxe Efficiency Studio
1 4
hotel , Chatham
Chatham, MA
02/07 – 11/07
£1868/nighttotal: £16812 (9 )
Waterfront Chatham Escape, Pet Friendly, Pond View
4 4
apartment , Chatham
Browse Holiday Rentals with a Spa in Chatham, MA
Choosing a holiday rental or Airbnb with a spa in Chatham, MA makes waterside wellness feel effortless. Spa bath access is included.
Chatham, MA
04/08 – 08/08
£546/nighttotal: £2184 (4 )
Charming 2-bedroom Pet Friendly House With Central Ac In Quiet Dennis Port Area
