This Dennis Port seaside cottage, an 8-minute (approximately 13 km) drive from Cape Cod Beaches and Sea Street Beach, offers stunning ocean views. The 76 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, a garden with barbecue, free parking, Wi-Fi, and air conditioning.
9.2 25 reviews
Chatham, MA
24/06 – 26/06
353 €/nighttotal: 706 € (2 )
Cozy Cape Cottage
1 3
cottage , Brewster
This Brewster holiday home is situated less than 2km from Nickerson State Park and several Cape Cod beaches, including Linnell Landing Beach and close to Ocean Edge Golf Club. This 46 square metre self-catering property sleeps three guests in two bedrooms and one bathroom, offering a fully equipped kitchen, Wi-Fi, a patio, garden, and parking.
Chatham, MA
24/06 – 26/06
677 €/nighttotal: 1354 € (2 )
Ping-pong & Backyard: Spacious Chatham Retreat
1 3
cottage , Chatham
This pet-friendly South Chatham holiday home is situated within 3km of Adventure Chatham, Forest Beach, and Cape Cod beaches, and under 5km from Cockle Cove and Ridgevale beaches. The self-catering property boasts three bathrooms, a fully equipped kitchen with oven, hob, microwave, and dishwasher, a private terrace, on-site BBQ facilities, free Wi-Fi in communal areas, and free parking.
Chatham, MA
04/08 – 08/08
468 €/nighttotal: 1872 € (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.
Best family friendly Chatham, MA cottages
Among the 72 accommodations in Chatham, MA, here are the 1 best family friendly cottages
9.2 25 reviews
Chatham, MA
24/06 – 26/06
353 €/nighttotal: 706 € (2 )
Cozy Cape Cottage
1 3
cottage , Brewster
This Brewster holiday home is situated less than 2km from Nickerson State Park and several Cape Cod beaches, including Linnell Landing Beach and close to Ocean Edge Golf Club. This 46 square metre self-catering property sleeps three guests in two bedrooms and one bathroom, offering a fully equipped kitchen, Wi-Fi, a patio, garden, and parking.
Best Chatham, MA cottages with a garden
Chatham, MA
04/08 – 08/08
461 €/nighttotal: 1844 € (4 )
New For 2026! 1/2 Mile To Swan Pond (2414)
2 2
cottage , Dennis
This Dennis Port seaside cottage, an 8-minute (approximately 13 km) drive from Cape Cod Beaches and Sea Street Beach, offers stunning ocean views. The 76 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, a garden with barbecue, free parking, Wi-Fi, and air conditioning.
Chatham, MA
24/06 – 26/06
677 €/nighttotal: 1354 € (2 )
Ping-pong & Backyard: Spacious Chatham Retreat
1 3
cottage , Chatham
This pet-friendly South Chatham holiday home is situated within 3km of Adventure Chatham, Forest Beach, and Cape Cod beaches, and under 5km from Cockle Cove and Ridgevale beaches. The self-catering property boasts three bathrooms, a fully equipped kitchen with oven, hob, microwave, and dishwasher, a private terrace, on-site BBQ facilities, free Wi-Fi in communal areas, and free parking.
9.2 25 reviews
Chatham, MA
24/06 – 26/06
353 €/nighttotal: 706 € (2 )
Cozy Cape Cottage
1 3
cottage , Brewster
This Brewster holiday home is situated less than 2km from Nickerson State Park and several Cape Cod beaches, including Linnell Landing Beach and close to Ocean Edge Golf Club. This 46 square metre self-catering property sleeps three guests in two bedrooms and one bathroom, offering a fully equipped kitchen, Wi-Fi, a patio, garden, and parking.
Frequently asked questions about cottages in Chatham, MA
What would be a good 1-day itinerary for visiting in and around Chatham, MA?
Start your day with a visit to Chatham Lighthouse, a historic landmark with stunning views of the Atlantic Ocean. Afterwards, explore the Chatham Bars Inn, a luxury resort with beautiful gardens and a lovely beach. In the afternoon, head to Chatham Fish Pier, where you can watch the fishermen unload their catch and enjoy some fresh seafood. For a taste of local history, stop by the Chatham Historical Society Museum before ending your day with dinner at one of Chatham's many excellent restaurants.
Chatham Lighthouse, the Chatham Bars Inn, Chatham Fish Pier, and the Chatham Historical Society Museum are all must-see attractions. You should also check out the Chatham Light Beach, a beautiful stretch of sand perfect for swimming, sunbathing, and enjoying the views.
What are the best cottages with a pool in Chatham, MA?
Can you easily explore Chatham, MA on foot or by bike?
Chatham is a relatively small town, so you can easily explore the main areas on foot. However, if you want to venture further afield, renting a bike is a great option. There are several bike rental shops in town, and there are plenty of scenic bike paths to explore.
What are the best cottages with a jacuzzi in Chatham, MA?
What activities are available in and around Chatham, MA?
Besides exploring the town and its sights, you can enjoy a variety of activities like swimming, sunbathing, fishing, kayaking, and whale watching. There are also several golf courses in the area, as well as a number of art galleries and shops.
What are the best cottages for families and kids in Chatham, MA?
What famous towns or cities are near to Chatham, MA?
Chatham is located on Cape Cod, which is known for its charming towns and villages. Some of the most popular destinations near Chatham include Provincetown, Falmouth, and Hyannis. If you want to explore beyond Cape Cod, Boston is about a two-hour drive away.
What are the best pet friendly cottages in Chatham, MA?
What are the most common amenities in cottages in Chatham, MA?
Most cottages in Chatham offer basic amenities like a kitchen, bathroom, and bedrooms. Many also have a fireplace, private deck, and access to a shared swimming pool or hot tub. Some cottages may also have additional amenities like a washer and dryer, cable TV, and Wi-Fi.
What are the best cottages with parking in Chatham, MA?
Among the 72 accommodations in Chatham, MA, here are the 1 best cottages with a jacuzzi
Chatham, MA
04/08 – 08/08
461 €/nighttotal: 1844 € (4 )
New For 2026! 1/2 Mile To Swan Pond (2414)
2 2
cottage , Dennis
This Dennis Port seaside cottage, an 8-minute (approximately 13 km) drive from Cape Cod Beaches and Sea Street Beach, offers stunning ocean views. The 76 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, a garden with barbecue, free parking, Wi-Fi, and air conditioning.
Best pet friendly Chatham, MA cottages
Among the 72 accommodations in Chatham, MA, here are the 2 best pet friendly cottages
Chatham, MA
24/06 – 26/06
677 €/nighttotal: 1354 € (2 )
Ping-pong & Backyard: Spacious Chatham Retreat
1 3
cottage , Chatham
This pet-friendly South Chatham holiday home is situated within 3km of Adventure Chatham, Forest Beach, and Cape Cod beaches, and under 5km from Cockle Cove and Ridgevale beaches. The self-catering property boasts three bathrooms, a fully equipped kitchen with oven, hob, microwave, and dishwasher, a private terrace, on-site BBQ facilities, free Wi-Fi in communal areas, and free parking.
Chatham, MA
04/08 – 08/08
468 €/nighttotal: 1872 € (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.
