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

Chatham Vacation Rentals

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Our top choices for Chatham vacation rentals

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 SAR 574
SAR 2,232 total
includes taxes & fees
31 Aug - 1 Sep
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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 SAR 458
SAR 1,896 total
includes taxes & fees
1 Sep - 2 Sep
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

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 SAR 1,262
SAR 2,626 total
includes taxes & fees
23 Sep - 24 Sep
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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 SAR 1,971
SAR 2,578 total
includes taxes & fees
10 Sep - 11 Sep
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

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 SAR 1,467
SAR 2,899 total
includes taxes & fees
9 Sep - 10 Sep
Beautiful home near Jacknife Beach and bike trail

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 SAR 1,690
SAR 3,438 total
includes taxes & fees
22 Sep - 23 Sep
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

7. Spacious 4BR house in perfect Chatham with AC

Spacious 4BR house in perfect Chatham with AC
Chatham
The price is SAR 2,275
SAR 4,581 total
includes taxes & fees
13 Sep - 14 Sep
Spacious 4BR house in perfect Chatham with AC

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 SAR 4,795
SAR 6,270 total
includes taxes & fees
21 Sep - 22 Sep
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

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 SAR 541
SAR 2,590 total
includes taxes & fees
1 Sep - 2 Sep
6 Mi to Beach: Home w/ Deck in Brewster!

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 SAR 391
SAR 2,651 total
includes taxes & fees
1 Sep - 2 Sep
Great for Families! Brewster Home 6 Mi to Beach

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 SAR 822
SAR 941 total
includes taxes & fees
24 Sep - 25 Sep
Brewster Green Resort

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 SAR 672
SAR 2,063 total
includes taxes & fees
7 Sep - 8 Sep
Cozy Large Home in Harwich with Patio near Wequassett Resort

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 traveler
The price is SAR 939
SAR 1,766 total
includes taxes & fees
20 Sep - 21 Sep
Quiet getaway in a unique area of Cape Cod

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 SAR 657
SAR 1,599 total
includes taxes & fees
12 Sep - 13 Sep
On Town Cove with salt water access! Kayaks and paddle board available for use!

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, (121 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is SAR 431
SAR 1,138 total
includes taxes & fees
24 Sep - 25 Sep
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

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 SAR 1,247
SAR 2,957 total
includes taxes & fees
2 Sep - 3 Sep
Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!

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

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 SAR 965
SAR 1,104 total
includes taxes & fees
30 Aug - 31 Aug
Edgewater Beach Resort

19. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (81 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 SAR 1,183
SAR 3,068 total
includes taxes & fees
6 Sep - 7 Sep
Family Cottage Close to Beach!!

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 SAR 1,464
SAR 3,386 total
includes taxes & fees
2 Sep - 3 Sep
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

Frequently asked questions

Can I find a vacation rental in Chatham?

Yes, you can find vacation rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you'd like a relaxing place to 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 vacation rentals that Chatham has to offer?

Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5: You might want to consider this vacation rental near Chatham, which is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Chatham?

With 275 Expedia vacation rentals, you're sure 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 vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chatham. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.