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.
$519 nightly
The price is $594
Aug 31 - Sep 1
Total with taxes and fees
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.
$441 nightly
The price is $505
Sep 1 - Sep 2
Total with taxes and fees
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.
$611 nightly
The price is $699
Sep 23 - Sep 24
Total with taxes and fees
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.
$600 nightly
The price is $687
Sep 10 - Sep 11
Total with taxes and fees
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.
$615 nightly
The price is $704
Sep 15 - Sep 16
Total with taxes and fees
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
$800 nightly
The price is $916
Sep 22 - Sep 23
Total with taxes and fees
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
$1,066 nightly
The price is $1,220
Sep 13 - Sep 14
Total with taxes and fees
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.
$1,387 nightly
The price is $1,588
Sep 21 - Sep 22
Total with taxes and fees
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
$603 nightly
The price is $690
Sep 1 - Sep 2
Total with taxes and fees
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.
$617 nightly
The price is $706
Sep 1 - Sep 2
Total with taxes and fees
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
$219 nightly
The price is $251
Sep 24 - Sep 25
Total with taxes and fees
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.
$496 nightly
The price is $549
Sep 7 - Sep 8
Total with taxes and fees
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
$413 nightly
The price is $473
Aug 29 - Aug 30
Total with taxes and fees
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.
$372 nightly
The price is $426
Sep 12 - Sep 13
Total with taxes and fees
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, (120 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
$266 nightly
The price is $304
Sep 24 - Sep 25
Total with taxes and fees
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.
$688 nightly
The price is $787
Sep 2 - Sep 3
Total with taxes and fees
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.
$839 nightly
The price is $961
Sep 3 - Sep 4
Total with taxes and fees
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
$268 nightly
The price is $307
Aug 30 - Aug 31
Total with taxes and fees
Edgewater Beach Resort

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.
$714 nightly
The price is $817
Sep 6 - Sep 7
Total with taxes and fees
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.
$760 nightly
The price is $870
Sep 8 - Sep 9
Total with taxes and fees
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

Find out more about Chatham

Everything you need to know about Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $251 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 home 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.