This Harwich Port cottage, a six-minute walk from Bank Street Beach, is conveniently located within 19-43km of attractions including the Nauset Lighthouse, Wellfleet Bay Wildlife Sanctuary, Heritage Museums & Gardens, and Cape Cod National Seashore. This self-catering property offers 120 square metres of space with one bedroom, two bathrooms, and sleeps up to seven guests, boasting a fully equipped kitchen, private parking, Wi-Fi, air conditioning, and a garden.
Chatham, MA
09/07 – 13/07
1387 €/nighttotal: 5548 € (4 )
Original School House In The Heart Of Chatham
4 6
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.
9.8 28 reviews
Chatham, MA
07/08 – 14/08
830 €/nighttotal: 5810 € (7 )
148 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 7
house , Chatham
This spacious Chatham house, near Ridgevale and Harding's Beaches (2.9km), offers easy access to Kream & Kone, Hanger B, and Marion's Pie Shop, all within 1.6km, and Chatham's Main Street (3.5km). The 148 square metre, single-storey property sleeps eight guests across three bedrooms and two bathrooms, boasting a fully fenced garden with deck, fire pit and outdoor shower, plus a spa, fitness centre, and free Xplorie tickets worth £600 for local attractions.
9.6 42 reviews
Chatham, MA
15/07 – 17/07
740 €/nighttotal: 1480 € (2 )
Chatham- Avail 6/28 -7/03 Walk 2 Beach, Dining
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.
9.7 35 reviews
Chatham, MA
25/06 – 27/06
526 €/nighttotal: 1052 € (2 )
Cockle Cottage - Renovated Chatham Cape House
1 4
apartment , Chatham
Cockle Cottage, a self-catering holiday home in South Chatham, Massachusetts, is conveniently located on Main Street (Route 28), less than 1.5km from Cockle Cove Beach on Nantucket Sound and offers easy access to Chatham's town centre. This single-storey property sleeps four guests in two bedrooms and one bathroom, featuring a well-equipped kitchenette, air conditioning, a private garden with an outdoor shower and fire pit, plus parking and Wi-Fi; nearby attractions include the Cape Cod Rail Trail.
8.5 2 reviews
Chatham, MA
25/06 – 27/06
602 €/nighttotal: 1204 € (2 )
Spacious W Large Outdoor Area Fire Pit
4 4
house , Chatham
This spacious Chatham holiday home, situated 2.1km from Oyster Pond Beach and within easy reach of attractions such as the Nauset Lighthouse (22.5km), Truro Historical Museum (45km), and Sandwich Glass Museum (48km), offers a convenient base for exploring Cape Cod. This 186 square metre property boasts a four-bedroom, two-bathroom layout, comfortably sleeping up to 15 guests and featuring a fully equipped kitchen, garden, parking, and air conditioning.
10 1 review
Chatham, MA
07/08 – 14/08
955 €/nighttotal: 6685 € (7 )
9 Reliance Way Harwich Cape Cod- -Norma's Cape Escape
1 7
house , Harwich
Norma's Cape Escape, a self-catering property in Harwich, Cape Cod, is conveniently located 22.5km from Wellfleet Bay Wildlife Sanctuary and 24km from Cape Cod National Seashore. This one-bedroom house boasts four bathrooms, sleeps 21 guests, includes a fully equipped kitchen with dishwasher, microwave and fridge, a garden, air conditioning, cable TV, a fireplace, and offers internet access.
9.3 3 reviews
Chatham, MA
25/06 – 27/06
577 €/nighttotal: 1154 € (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.
9.3 84 reviews
Chatham, MA
04/08 – 08/08
505 €/nighttotal: 2020 € (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.
10 2 reviews
Chatham, MA
25/06 – 27/06
667 €/nighttotal: 1334 € (2 )
Cape Escape - Family-friendly Chatham Retreat
2 4
apartment , Chatham
This Chatham seaside property is situated less than 3.2km from the Chatham Marconi Maritime Center and Cape Cod beaches, and under 4.8km from Ridgevale Beach and the Chatham Shark Center. This 111 square metre house boasts three bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, terrace, garden, spa, parking, and on-site laundry facilities.
Chatham, MA
25/06 – 27/06
836 €/nighttotal: 1672 € (2 )
Harwich Coastal Cottage: Cape Gem In Harwich Port
3 4
apartment , Harwich
This Harwich Port holiday home is situated a short walk from Cape Cod beaches and a short drive from attractions including the Cape Cod Inflatable Park and Cape Codder Water Park. The 120-square-metre property boasts three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, air conditioning, Wi-Fi, a private fenced yard, BBQ facilities, and access to an on-site water park.
10 70 reviews
Chatham, MA
09/07 – 13/07
1066 €/nighttotal: 4264 € (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.
Best family friendly Chatham, MA holiday rentals
Among the 1015 accommodations in Chatham, MA, here are the 4 best family friendly rentals
9.0 44 reviews
Chatham, MA
15/07 – 17/07
457 €/nighttotal: 914 € (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.
10 1 review
Chatham, MA
04/08 – 08/08
591 €/nighttotal: 2364 € (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.
Chatham, MA
25/06 – 27/06
574 €/nighttotal: 1148 € (2 )
Cape Escape Harwich
1 4
apartment , Harwich
This family-friendly Cape Cod property is located a short drive from Harwich and Chatham, providing convenient access to venues such as Wequassett Inn, Wychmere, and Chatham Bars Inn. This spacious 3-bedroom apartment accommodates up to 8 guests and features a large garden, deck with an outdoor shower, a well-equipped kitchen, and complimentary baby gear, with beach chairs and towels provided for easy access to nearby shores.
Chatham, MA
04/08 – 08/08
1006 €/nighttotal: 4024 € (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
01/07 – 06/07
2060 €/nighttotal: 10300 € (5 )
Wequassett Resort And Golf Club
1 2
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
309 €/nighttotal: 618 € (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.
9.2 37 reviews
Chatham, MA
15/07 – 17/07
711 €/nighttotal: 1422 € (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.
9.6 4 reviews
Chatham, MA
15/07 – 17/07
335 €/nighttotal: 670 € (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.
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 haven for outdoor activities! You can go fishing, kayaking, or paddleboarding in the harbour. In the summer, you can also enjoy swimming at the Chatham beaches or taking a boat trip to see the local seals and whales.
What are the best Airbnb and holiday rentals in Chatham, MA?
What other towns or cities can be easily accessed from Chatham, MA?
Chatham is well-connected to other towns in the area. You can easily drive to nearby towns like Harwich Port, Orleans, and Provincetown. If you want to explore further afield, Boston is about a 2-hour drive away.
What amenities are commonly available in vacation rentals in Chatham, MA?
Vacation rentals in Chatham usually have all the amenities you need for a comfortable stay. Most rentals offer fully equipped kitchens, laundry facilities, Wi-Fi, and outdoor spaces like patios or decks. Some rentals even have private pools or hot tubs.
What are the best holiday 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, with beautiful weather and plenty of outdoor activities. However, if you prefer a quieter experience, you can visit in the shoulder seasons of spring or autumn.
What are the best rentals for families and kids in Chatham, MA?
Chatham's cuisine is heavily influenced by its coastal location. You'll find plenty of fresh seafood dishes, like clam chowder, lobster rolls, and grilled fish. Don't miss the local cranberry dishes, which are a staple of the region.
What are the best rentals or Airbnbs with a jacuzzi in Chatham, MA?
Modern Fairway Condo With Open Layout, Private Patio, Ac & Washer/dryer
2 2
apartment , Brewster
This garden-level condominium is located in Brewster's Ocean Edge Resort community, adjacent to a golf course and within a short drive of local beaches, shops, and restaurants. This 87 square metre apartment offers two bedrooms and two bathrooms, accommodating up to six guests with a renovated kitchen, in-unit laundry, and air conditioning, while being conveniently situated minutes from the Cape Cod Rail Trail for cycling and walking.
Chatham, MA
15/07 – 17/07
624 €/nighttotal: 1248 € (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
25/06 – 27/06
1158 €/nighttotal: 2316 € (2 )
557 Route 28, Unit 202, Harwich Port Cape Cod - -Dolce Vita
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.
8.9 56 reviews
Chatham, MA
04/08 – 08/08
581 €/nighttotal: 2324 € (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.
Best Chatham, MA holiday rentals with parking
9.0 4 reviews
Chatham, MA
07/08 – 14/08
1661 €/nighttotal: 11627 € (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.
9.1 1099 reviews
Chatham, MA
07/08 – 14/08
8980 €/nighttotal: 62860 € (7 )
Chatham Bars Inn
4 7
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.
8.6 18 reviews
Chatham, MA
04/08 – 08/08
673 €/nighttotal: 2692 € (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.
10 1 review
Chatham, MA
25/06 – 27/06
353 €/nighttotal: 706 € (2 )
Renovated 2nd-floor Corner Unit, New Interiors. Beach, Parking Passes On Us.
1 4
apartment , Brewster
This recently renovated one-bedroom flat is located within the Ocean Edge resort in Brewster, offering convenient access to Cape Cod Beaches and Nickerson State Park, just 1.6 kilometres away. This apartment accommodates up to four guests with a queen bed and a sleeper sofa, featuring a fully equipped kitchen, air conditioning, a balcony, garden access, and dedicated parking, with beach chairs and towels provided for your use.