A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Chatham Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chatham holiday rentals

TV, fireplace

1. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (105 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is HK$1,199
HK$4,660 total
includes taxes & fees
31 Aug - 1 Sept
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
TV, offices

2. Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Chatham
10.0 out of 10, Exceptional, (1 review)
"Lovely spot on the water!"
United States
Elizabeth T.
The price is HK$956
HK$3,957 total
includes taxes & fees
1 Sept - 2 Sept
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Exterior

3. Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham
10.0 out of 10, Exceptional, (127 reviews)
"Our stay was wonderful!"
United States
Corinne J.
The price is HK$2,634
HK$5,482 total
includes taxes & fees
23 Sept - 24 Sept
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Dining

4. Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Chatham
10.0 out of 10, Exceptional, (107 reviews)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
The price is HK$4,115
HK$5,383 total
includes taxes & fees
10 Sept - 11 Sept
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Sun-loungers, beach towels

5. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (85 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
The price is HK$3,528
HK$6,666 total
includes taxes & fees
17 Sept - 18 Sept
Beautiful home near Jacknife Beach and bike trail
Exterior

6. Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Lock didn’t work"
United States
Claudine
The price is HK$3,527
HK$7,177 total
includes taxes & fees
22 Sept - 23 Sept
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
Property grounds

7. Spacious 4BR house in perfect Chatham with AC

Spacious 4BR house in perfect Chatham with AC
Chatham
The price is HK$4,749
HK$9,563 total
includes taxes & fees
13 Sept - 14 Sept
Spacious 4BR house in perfect Chatham with AC
Exterior

8. Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Chatham
10.0 out of 10, Exceptional, (21 reviews)
"House was wonderful with plenty of room. Great outdoor spaces with a deck and patio. Very convenient location. Host responsive to our needs. Would definitely stay again. "
United States
Sally S.
The price is HK$10,039
HK$13,123 total
includes taxes & fees
21 Sept - 22 Sept
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Front of property

9. 6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is HK$1,129
HK$5,407 total
includes taxes & fees
20 Sept - 21 Sept
6 Mi to Beach: Home w/ Deck in Brewster!
Outdoor dining

10. Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
10.0 out of 10, Exceptional, (11 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is HK$815
HK$5,535 total
includes taxes & fees
1 Sept - 2 Sept
Great for Families! Brewster Home 6 Mi to Beach
Indoor spa tub

11. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (141 reviews)
"Clean, good activities for the kids and pools were nice"
United States
Jim
The price is HK$1,717
HK$1,965 total
includes taxes & fees
24 Sept - 25 Sept
Brewster Green Resort
Pool

12. Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (13 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is HK$1,403
HK$4,307 total
includes taxes & fees
13 Sept - 14 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
Sun-loungers

13. Quiet getaway in a unique area of Cape Cod

Quiet getaway in a unique area of Cape Cod
Brewster
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for a quiet getaway. Owner was in Constant contact. If I had a question replied very quickly. I highly recommend staying here."
United States
Anonymous traveller
The price is HK$1,960
HK$3,705 total
includes taxes & fees
29 Aug - 30 Aug
Quiet getaway in a unique area of Cape Cod
Beach nearby, sun-loungers

14. On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (63 reviews)
"Clean, great location. "
United States
Peter G.
The price is HK$1,372
HK$3,337 total
includes taxes & fees
12 Sept - 13 Sept
On Town Cove with salt water access! Kayaks and paddle board available for use!
Beach

15. Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.8 out of 10, Exceptional, (120 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is HK$900
HK$2,375 total
includes taxes & fees
24 Sept - 25 Sept
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Smart TV, fireplace, books

16. Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!

Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!
Harwich
9.6 out of 10, Exceptional, (5 reviews)
"We had an amazing stay! The house was exactly what we were looking for when booking. The host was amazing and accommodating for our dates. Communication was easy and responsive. We look forward to booking again in the future. "
United States
Laura J.
The price is HK$2,603
HK$6,173 total
includes taxes & fees
2 Sept - 3 Sept
Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!
Terrace/patio

17. New! 4BR Fire Pit, Ping Pong, Movie Room

New! 4BR Fire Pit, Ping Pong, Movie Room
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"Very responsive and friendly host. "
United States
Matt M.
New! 4BR Fire Pit, Ping Pong, Movie Room
Private beach

18. Edgewater Beach Resort

Edgewater Beach Resort
3.5 star property
Dennis Port
9.0 out of 10, Wonderful, (338 reviews)
"Great place! Everything was lovely"
United States
Susan
The price is HK$2,189
HK$2,506 total
includes taxes & fees
31 Aug - 1 Sept
Edgewater Beach Resort
Exterior

19. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (80 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is HK$2,469
HK$6,405 total
includes taxes & fees
6 Sept - 7 Sept
Family Cottage Close to Beach!!
Outdoor dining

20. Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location "
United States
Norman Y.
The price is HK$2,861
HK$6,818 total
includes taxes & fees
8 Sept - 9 Sept
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Cape Sands Inn

Cape Sands Inn

8/10 Good
"This motel (doors open to the outdoors) was a quick overnight stop for us, arriving at 9:15 pm and leaving by 10 am. BE CAREFUL as check-in is supposed to be before 9pm unless you have made other arrangements. We did not realize this and were lucky that the office was still open. We are aware of 2 other reservations that arrived just before/after 10. We did not use any of the amenities, but they all looked nice. There is a nice fire pit, corn hole boards, grills and other outdoor amenities. The hotel is set up like a block letter U. We had the back/bottom section and it had a beautiful view of water. We even watched ducks swimming and a chatty kingfisher catching fish. The room itself was MOSTLY very clean. No microwave. The bathroom, towels, bedding, fridge, etc were great/clean. The carpet was disgustingly dirty turning our socks dark gray. I put our towels on the floor after our showers so we didn't have to walk on the carpet. I did mention this on checkout and (supposedly) maintenance was going to clean the carpet. It had been vacuumed, but needed steam cleaning. If we needed to, we could stay there again."
Amy 1-night trip
Posted 5 hours ago
Cape Sands Inn

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Can I find a holiday rental in Chatham?

Yes, there are holiday rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the popular beaches and waterfront in Chatham. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Chatham has to offer?

Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5: This holiday home rental outside of Chatham is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chatham?

With 275 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Chatham Railroad Museum and Chatham Drama Guild, whereas Cape Cod Beaches and Chatham Lighthouse Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Ridgevale Beach are other places worth a visit.

What are holiday rentals like in Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chatham. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.