The 10 best holiday rentals in Chatham, USA | Booking.com
Skip to main content

Holiday Rentals in Chatham

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Chatham

The best holiday rentals in Chatham

Check out our pick of great holiday rentals in Chatham

Show hotels on map

Filter by:

Review score

Old Harbor Inn

Chatham

This Chatham bed and breakfast is a 3-minute drive the Cape Cod National Seashore. The inn features a gym and rooms equipped with a flat-screen TV.

B
Barry
From
Ireland
Perfect location, great hosts, super breakfasts and excellent rooms and facilities. Highly recommended.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 89 reviews
Price from
US$439
1 night, 2 adults
Check availability

Sea House

Chatham

Sea House is located in Chatham, 26 km from Nauset Lighthouse, 28 km from Wellfleet Bay Wildlife Sanctuary, and 30 km from Cape Cod National Seashore.

J
Jennifer
From
United States
Fabulous little cottage in quaint Cape Cod. Far away from noise and other people. On a cute short dirt road- magical! Loved everything about it. We wish we had been able to stay at least two more nights!
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 17 reviews
Price from
US$283
1 night, 2 adults
Check availability

Lucky Number Seven

Chatham

Boasting air-conditioned accommodation with a patio, Lucky Number Seven is situated in Chatham.

V
Vivienne
From
United Kingdom
Well equiped. Secluded back garden. Enjoyed seeing chipmunks and rabbits.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 12 reviews
Price from
US$407
1 night, 2 adults
Check availability

Cape Cod Villa

Harwich (Near Chatham)

Featuring air-conditioned accommodation with a patio, Cape Cod Villa is set in Harwich. This property offers access to a balcony, a pool table, free private parking and free WiFi.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 15 reviews
Price from
US$481.95
1 night, 2 adults
Check availability

Sesuit Harbor House

East Dennis (Near Chatham)

Sesuit Harbor House features a seasonal outdoor swimming pool, garden, a shared lounge and terrace in East Dennis.

M
Michael
From
Canada
Phil & Silvia were great hosts, and made us feel welcome from check-in, all the way through to our last minutes on the property. They provided plenty of recommendations; places to eat, things to do and see, etc. The room was spacious, clean and well laid out. Lots of windows to let in natural light. The bed was comfortable, and the bedding was clean. All amenities were provided (soap, shampoo, towels, etc.). The water pressure in the shower was great. Air conditioning worked well. The property was no different, it was very well maintained. Lots of thoughtful touches throughout the property; bean bag toss, mini soccer nets, lots of chairs around the pool. There was a grilling area with grilling utensils. There was also a family of resident goats tucked away in their own little corner of the property. They provided complimentary continental breakfast each morning. They provided us with bikes (incl. Helmet and bike lock) to ride around town and fitness equipment (yoga mats, small weights, elastic bands, foam roller, etc.) to do some exercises in our room. Great location, nearby to great restaurants, ice cream, liquor, convenience stores, beaches, etc... We can't say enough good things about this place and would recommend Sesuit Harbor House to anyone visiting Cape Cod.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 157 reviews
Price from
US$220.64
1 night, 2 adults
Check availability

Scallop's Nest

Dennis Port (Near Chatham)

Scallop's Nest, a property with a garden, is located in Dennis Port, 34 km from Wellfleet Bay Wildlife Sanctuary, 37 km from Cape Cod National Seashore, as well as 38 km from Sandwich Glass Museum.

D
Donovan
From
United Kingdom
The property was in a great location and had everything needed for a great vacation in Cape Cod. There was an initial issue with the cleaning of the property on arrival due to unforeseen circumstances regarding the cleaning staff but the owner quickly rectified the situation and was extremely helpful throughout our stay. We would highly recommend this property for a stay by the coast in Cape Cod.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 7 reviews
Price from
US$225
1 night, 2 adults
Check availability

Candleberry Inn on Cape Cod

Brewster (Near Chatham)

Offering garden views, Candleberry Inn on Cape Cod is an accommodation set in Brewster, 1.1 km from Breakwater Beach and 19 km from Nauset Lighthouse.

E
Eduardo
From
Brazil
the hotel owners and the staff pay attention to every detail, the room is very comfortable and the breakfast was the better we had in the US in the course of 20 days.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 40 reviews
Price from
US$350.55
1 night, 2 adults
Check availability

Captain Farris House

South Yarmouth (Near Chatham)

Offering free WiFi access, Captain Farris House Bed & Breakfast is located in South Yarmouth, just steps from the shops and restaurants of the town centre.

T
Tony
From
United Kingdom
charming characterful house where the hosts go the extra mile to make you feel comfortable and feel at home. Fabulous freshly cooked breakfast cooked with love.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 96 reviews
Price from
US$199
1 night, 2 adults
Check availability

By The Sea Guests Bed & Breakfast and Suites

Dennis Port (Near Chatham)

By The Sea Guests Bed & Breakfast and Suites is set on the seafront in Dennis Port, 70 metres from Sea Street Beach and 32 km from Nauset Lighthouse.

g
georgina
From
United Kingdom
Amazing location and Tom made us very welcome and thanks for the upgrade so great of you
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 75 reviews
Price from
US$182.85
1 night, 2 adults
Check availability

Ocean Edge resort two bedroom and two bathroom condo.

Brewster (Near Chatham)

Situated in Brewster, 2 km from Ellis Landing Beach and 19 km from Nauset Lighthouse, Ocean Edge resort two bedroom and two bathroom condo. Offers a garden and air conditioning.

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 14 reviews
Price from
US$145.80
1 night, 2 adults
Check availability
All holiday rentals in Chatham

Most booked holiday rentals in Chatham and surroundings in the past month

See all

Enjoy breakfast in Chatham and nearby

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 2 reviews

    Situated in Chatham, 600 metres from Oyster Pond Beach and 24 km from Nauset Lighthouse, Centrally Located Home w Patio Fire Pit offers a garden and air conditioning.

  • Situated in Chatham, less than 1 km from Chatham Lighthouse Beach and 25 km from Nauset Lighthouse, 388 Main Street Chatham Cape Cod - - The Priscilla House offers air conditioning.

  • Located in Chatham, 1.2 km from Oyster Pond Beach and 23 km from Nauset Lighthouse, 40 Tip Cart Drive Chatham Cape Cod - The Hideaway offers a garden and air conditioning.

  • Located in Chatham, less than 1 km from Oyster Pond Beach and 25 km from Nauset Lighthouse, Steps to Oyster Pond Private Dock! offers a garden and air conditioning.

  • Set in Chatham, 200 metres from Chatham Lighthouse Beach and 25 km from Nauset Lighthouse, 201 Main Street Chatham Cape Cod - - Sandpiper offers air conditioning. A hot tub is available for guests.

  • Boasting air-conditioned accommodation with a private pool, 14 Hallet Lane Chatham Cape Cod - - Sand Simeon is situated in Chatham.

  • Situated in Chatham, less than 1 km from Oyster Pond Beach and 25 km from Nauset Lighthouse, On the Chatham Loop - 1 Min to the Beach offers a garden and air conditioning.

  • Situated in Chatham, 24 km from Nauset Lighthouse and 26 km from Wellfleet Bay Wildlife Sanctuary, 1 Mi to Town and Oyster Pond Beach Chatham Retreat offers a garden and air conditioning.

Highly rated holiday rentals in Chatham and nearby

  • Cape Cod Villa

    Harwich
    8.0+ review score
    Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 15 reviews

    Featuring air-conditioned accommodation with a patio, Cape Cod Villa is set in Harwich. This property offers access to a balcony, a pool table, free private parking and free WiFi.

    From US$930.31 per night

  • Jesmond Cottage

    Harwich
    8.0+ review score
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Located in Harwich, 24 km from Nauset Lighthouse and 26 km from Wellfleet Bay Wildlife Sanctuary, Jesmond Cottage offers air conditioning.

  • Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 5 reviews

    Located in Harwich, 400 metres from Red River Beach and 26 km from Nauset Lighthouse, 5 Min Walk to Red River Beach offers a garden and air conditioning.

  • The Spray

    Harwich Port
    8.0+ review score
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 7 reviews

    Boasting accommodation with a patio, The Spray is situated in Harwich Port.

These holiday rentals in Chatham and nearby have options with free cancellation

  • Stepping Stone Cottage

    Chatham
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 2 reviews

    Set 23 km from Nauset Lighthouse, 25 km from Wellfleet Bay Wildlife Sanctuary and 27 km from Cape Cod National Seashore, Stepping Stone Cottage features accommodation located in Chatham.

  • Lovely Home Near Bike Path Dog Welcome!

    Chatham
    Free cancellation options available
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Situated in Chatham, 2 km from Oyster Pond Beach and 23 km from Nauset Lighthouse, Lovely Home Near Bike Path Dog Welcome! offers a garden and air conditioning.

  • Located on Rail Trail By Beach & Downtown

    Chatham
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Set in Chatham, 2 km from Oyster Pond Beach and 23 km from Nauset Lighthouse, Located on Rail Trail By Beach & Downtown offers a garden and air conditioning.

  • Great Chatham Location Near Beach

    Chatham
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Situated in Chatham, 2.4 km from Oyster Pond Beach and 22 km from Nauset Lighthouse, Great Chatham Location Near Beach offers a garden and air conditioning.

  • Spacious w Large Outdoor Area Fire Pit

    Chatham
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 2 reviews

    Situated in Chatham, 2.1 km from Oyster Pond Beach and 23 km from Nauset Lighthouse, Spacious w Large Outdoor Area Fire Pit offers a garden and air conditioning.

  • Queen Anne

    Chatham
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 2 reviews

    Located in Chatham, 2.2 km from Oyster Pond Beach and 23 km from Nauset Lighthouse, Queen Anne provides a restaurant. Guests can benefit from a patio and an outdoor fireplace.

  • Stellar Home with Hot Tub & Movie Room

    Chatham
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Set in Chatham, 2.6 km from Oyster Pond Beach and 25 km from Nauset Lighthouse, Stellar Home with Hot Tub & Movie Room offers a garden and air conditioning.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Situated in Chatham, 2.5 km from Oyster Pond Beach and 25 km from Nauset Lighthouse, 31 Bayview Street Chatham Cape Cod- -The Way Home offers air conditioning.

FAQ about holiday rentals in Chatham

Holiday rentals that guests love in Chatham

See all

  • Central AC Close to Beach Dog Friendly!

    Holiday Rental in Chatham
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 3 reviews
    Superb holiday home . Lovely quiet location yet easy access to shops,restaurants and beaches.great base to explore Cape Cod. Home was clean,well equipped and plenty of space for our family of 4. Would highly recommend.
    Guest review by
    Lucy
    Solo traveller

Research, refine and make plans for your whole trip

Holiday Rentals in the United States

Eager to explore more of the United States? Find hotels up and down the country!

Holiday Rentals in Cape Cod

Extend your search and explore the surrounding area.

Holiday Rentals in Massachusetts

Extend your search and explore the surrounding area.

Car hire in Chatham

Hire a car and hit the road.

Holiday Rentals in Hyannis

Find more hotels in a city close to Hyannis.

Holiday Rentals in Provincetown

Find more hotels in a city close to Provincetown.

Holiday Rentals in Booth Corner

Want to extend your trip or still just browsing? Try Booth Corner, also popular with our guests!

Holiday Rentals in New Woodstock

Try another destination popular with our guests.

Holiday Rentals in New York

Discover another destination in the United States.