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
$756/nighttotal: $3024 (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
$746/nighttotal: $2984 (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.
9.2 25 reviews
Chatham, MA
24/06 – 26/06
$570/nighttotal: $1140 (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.
8.6 4 reviews
Chatham, MA
15/08 – 22/08
$1574/nighttotal: $11018 (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.
Best family friendly Chatham, MA cottage rentals
Among the 72 accommodations in Chatham, MA, here are the 2 best family friendly cottage rentals
8.6 4 reviews
Chatham, MA
15/08 – 22/08
$1574/nighttotal: $11018 (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.
9.2 25 reviews
Chatham, MA
24/06 – 26/06
$570/nighttotal: $1140 (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
24/06 – 26/06
$1095/nighttotal: $2190 (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.
8.6 4 reviews
Chatham, MA
15/08 – 22/08
$1574/nighttotal: $11018 (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.
Chatham, MA
04/08 – 08/08
$746/nighttotal: $2984 (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.
9.2 25 reviews
Chatham, MA
24/06 – 26/06
$570/nighttotal: $1140 (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 offering stunning views of the coastline. Afterwards, head to Chatham Bars Inn for a delicious lunch and enjoy the beautiful beach. In the afternoon, explore the Chatham Historical Society Museum and learn about the town's rich history. For dinner, try the fresh seafood at The Chatham Squire.
Chatham Lighthouse is a must-see, with its iconic red and white stripes. The Chatham Bars Inn is a beautiful hotel with a stunning location on the beach. The Chatham Historical Society Museum offers a glimpse into the town's past, and the Chatham Fish Pier is a lively spot to watch fishermen unload their catch.
What are the best cottage rentals 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, to reach some of the beaches and more distant attractions, you'll need to drive or rent a bike. There are several bike rental shops in town.
What are the best cottage rentals with a jacuzzi in Chatham, MA?
What activities are available in and around Chatham, MA?
Chatham offers a range of activities, from swimming and sunbathing on the beautiful beaches to exploring the Chatham Light and the Chatham Historical Society Museum. You can also go whale watching, kayaking, or fishing. For a more relaxed experience, visit the Chatham Farmers Market or take a scenic drive along the Cape Cod National Seashore.
What are the best cottage rentals for families and kids in Chatham, MA?
What famous towns or cities are near to Chatham, MA?
Chatham is located on Cape Cod, a peninsula known for its charming towns and beautiful coastline. Nearby towns include Harwich Port, Dennis Port, and Orleans. The city of Boston is about a 2-hour drive from Chatham.
What are the best pet friendly cottage rentals in Chatham, MA?
What are the most common amenities in cottages in Chatham, MA?
Most cottages in Chatham offer amenities like fully equipped kitchens, private bathrooms, and laundry facilities. Some may also have outdoor spaces like decks or patios, fireplaces, and access to private beaches or pools.
What are the best cottage rentals with parking in Chatham, MA?
Among the 72 accommodations in Chatham, MA, here are the 1 best cottage rentals with a jacuzzi
Chatham, MA
24/06 – 26/06
$1095/nighttotal: $2190 (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.
Best pet friendly Chatham, MA cottage rentals
Among the 72 accommodations in Chatham, MA, here are the 3 best pet friendly cottage rentals
Chatham, MA
04/08 – 08/08
$756/nighttotal: $3024 (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.
8.6 4 reviews
Chatham, MA
15/08 – 22/08
$1574/nighttotal: $11018 (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.
Chatham, MA
24/06 – 26/06
$1095/nighttotal: $2190 (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.
