Best Holiday rentals and Airbnb offers in Chatham, MA
9.8 19 reviews
Chatham, MA
25/06 – 27/06
SG$822/nighttotal: SG$1644 (2 )
Jean's Dream - Renovated Chatham House
1 4
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.
Chatham, MA
01/07 – 06/07
SG$1064/nighttotal: SG$5320 (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.
Chatham, MA
01/07 – 06/07
SG$3933/nighttotal: SG$19665 (5 )
Kelley Lane - Cht- Kl161
1 2
house , Chatham
This detached house in Chatham is located 2.9 kilometres from Oyster Pond Beach and offers convenient access to regional attractions such as Nauset Lighthouse (25.7 kilometres) and Wellfleet Bay Wildlife Sanctuary (27.3 kilometres). This property boasts a floor area of 389 square meters, accommodating up to 19 guests across 4 bedrooms and 5 bathrooms, with amenities including air conditioning, WiFi, a fully equipped kitchen with a dishwasher and oven, a washing machine, and private parking, whilst also facilitating activities like cycling in the Chatham 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.
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.
9.8 35 reviews
Chatham, MA
07/08 – 14/08
SG$4763/nighttotal: SG$33341 (7 )
Historic Sea Captain's Home In Downtown Chatham
8 7
apartment , Chatham
This spacious eight-bedroom, five-bathroom dwelling is centrally located in Chatham town centre, a mere 644 metres from Andrew Harding's Beach and 966 metres from Lighthouse Beach, offering convenient access to Main Street amenities. This property provides ample space for eighteen guests with a state-of-the-art kitchen, expansive outdoor living areas including a private garden with a grill, and complimentary daily tickets to local attractions through Xplorie.
9.7 33 reviews
Chatham, MA
04/08 – 08/08
SG$660/nighttotal: SG$2640 (4 )
Pet-friendly Cape Escape 6 Min To Beach
1 2
apartment , Harwich
This pet-friendly house is located just 2.6 kilometres from Red River Beach, offering easy access to one of Harwich's most beautiful natural attractions. It boasts excellent ratings for location, cleanliness and user experience. The spacious house has two bedrooms, comfortably accommodating up to five guests. Amenities include a fully equipped kitchen, a large deck with a gas grill, Wi-Fi, air conditioning, and an outdoor shower.
9.8 53 reviews
Chatham, MA
15/07 – 17/07
SG$953/nighttotal: SG$1906 (2 )
Classic Home With Deck, Patio & Yard - Walk To Cockle Cove & Forest Beaches
3 2
apartment , Chatham
This South Chatham flat is situated a block from Main Street and 750 metres from Forest Beach, offering proximity to local attractions. This 138 square metre dwelling accommodates six guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, free WiFi, a fenced yard, private deck, outdoor shower, and gas grill.
Chatham, MA
04/08 – 08/08
SG$2061/nighttotal: SG$8244 (4 )
Original School House In The Heart Of Chatham
4 2
apartment , Chatham
This historic apartment, a former schoolhouse built in 1869, is located in Chatham Village, just a short walk from Lighthouse Beach, local shops, and restaurants. Offering accommodation for up to 8 guests, this four-bedroom, three-and-a-half-bathroom property features air conditioning throughout, a private kitchenette in the master suite, an outdoor shower, a gas grill, and an upper deck with views of Mill Pond.
10 1 review
Chatham, MA
25/06 – 27/06
SG$1651/nighttotal: SG$3302 (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.
Chatham, MA
07/08 – 14/08
SG$1853/nighttotal: SG$12971 (7 )
Beautiful Renovated Chatham Home
1 7
apartment , Chatham
This Chatham holiday home, situated on a quiet side road, is a 5-minute drive from Chatham's beaches and town centre and a 0.6km walk from Lovers Lake. This recently renovated (2020) 279 sq m property boasts three bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, air conditioning, private lake access with kayaks, and a garden with parking.
Chatham, MA
04/08 – 08/08
SG$728/nighttotal: SG$2912 (4 )
Serene Retreat With Cove Views
1 2
house , Eastham
This Eastham holiday cottage is located approximately 8.4 kilometres from Nauset Lighthouse, with attractions such as Truro Historical Museum (30.6 kilometres), Commercial Street (41.8 kilometres), and Pilgrim Monument (41.8 kilometres) within a 30.6 to 43.5 kilometre radius. This property accommodates up to three guests with one bedroom and one bathroom, featuring air conditioning, a microwave oven, a fridge, and cable television, whilst being conveniently situated 10.3 kilometres from Wellfleet Bay Wildlife Sanctuary and 12.7 kilometres from Cape Cod National Seashore.
Best family friendly Chatham, MA holiday rentals
Among the 1015 accommodations in Chatham, MA, here are the 4 best family friendly rentals
10 1 review
Chatham, MA
07/08 – 14/08
SG$2015/nighttotal: SG$14105 (7 )
143 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 7
house , Chatham
This Chatham holiday home is situated in a peaceful neighbourhood, 0.8km from Chatham Lighthouse, 2.1km from Chatham town centre, and a short walk to Lighthouse Beach and Outermost Harbour. The 142 square metre property boasts three ensuite bedrooms sleeping eight, a spacious wraparound deck with ocean views, and amenities including a gas grill, fire pit, and Xplorie's free local attraction tickets offer.
9.2 37 reviews
Chatham, MA
15/07 – 17/07
SG$1057/nighttotal: SG$2114 (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.
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
15/07 – 17/07
SG$901/nighttotal: SG$1802 (2 )
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.
Best Chatham, MA holiday rentals with a pool
Among the 1015 accommodations in Chatham, MA, here are the 4 best rentals with a pool
9.6 5 reviews
Chatham, MA
07/08 – 14/08
SG$1154/nighttotal: SG$8078 (7 )
House ∙ 3 Bedrooms ∙ 8 Guests
3 7
house , Chatham
Azure Cottage, situated in Chatham's Oyster Pond area, is less than 1.6km from Chatham town centre and under 3.2km from Chatham's beaches. This three-bedroom, two-bathroom property sleeps eight, boasts a private 0.6-hectare garden, hot tub, swimming pool, and fitness centre, plus a $750 Xplorie package offering free local attraction tickets.
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.
9.6 4 reviews
Chatham, MA
15/07 – 17/07
SG$498/nighttotal: SG$996 (2 )
Charming Studio Dennis Port Getaway With Wifi And Ac - Close To Beach!
1 2
studio , Dennis
This Dennis Port apartment is conveniently located a mere 640 metres from Cape Cod Beaches and 1.3 kilometres from Sea Street Beach, offering easy access to coastal activities. This studio apartment, measuring 19 square metres and accommodating two guests, features air conditioning, Wi-Fi, a kitchenette with a microwave and fridge, and access to a shared swimming pool and private terrace.
9.1 1099 reviews
Chatham, MA
09/07 – 13/07
SG$9678/nighttotal: SG$38712 (4 )
Chatham Bars Inn
3 6
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.
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?
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.
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.
8.3 2767 reviews
Chatham, MA
04/08 – 08/08
SG$813/nighttotal: SG$3252 (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.
Chatham, MA
25/06 – 27/06
SG$920/nighttotal: SG$1840 (2 )
Harwich Getaway By Leavetown Vacations
3 4
house , Harwich
This Harwich holiday home is situated approximately 26 kilometres from Nauset Lighthouse, 29 kilometres from Wellfleet Bay Wildlife Sanctuary, and 31 kilometres from Cape Cod National Seashore. This spacious property boasts 663 square metres of floor area, offering three bedrooms, three bathrooms, and sleeps up to eleven guests, complete with a fully equipped kitchen, private garden, free Wi-Fi, parking, and an on-site restaurant.
Best Chatham, MA holiday rentals with parking
9.9 58 reviews
Chatham, MA
01/07 – 06/07
SG$366/nighttotal: SG$1830 (5 )
Door To Shore In A Hop, Skip, And A Jump!
1 2
apartment , Harwich
This Harwich apartment, ideally located 0.5 km from Bank Street Beach and within walking distance of Main Street's shops and restaurants, offers easy access to Wychmere wedding venue (0.8 km). The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen, private deck with bocce and cornhole, beach essentials, and free Wi-Fi; weekly cleaning is provided for stays of two weeks or more.
Chatham, MA
07/08 – 14/08
SG$2554/nighttotal: SG$17878 (7 )
Slow M'ocean – A Fresh Take On Cape Calm
1 7
house , Chatham
Slow M'Ocean, a one-bedroom house in Chatham, is a six-minute walk from Chatham Lighthouse Beach and within 27-30km of Nauset Lighthouse, Wellfleet Bay Wildlife Sanctuary, and Cape Cod National Seashore. This pet-friendly property sleeps 15 guests, boasting four bathrooms, a fully equipped kitchen with dishwasher, air conditioning, cable TV, a fireplace, and internet access; nearby attractions include Chatham's town centre and Cape Cod Gateway Airport (30km).
8.9 56 reviews
Chatham, MA
04/08 – 08/08
SG$863/nighttotal: SG$3452 (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.
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.