Chatham Vacation Rentals

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Chatham vacation rentals

Terrace/patio
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Chatham
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
$291 nightly
The price is $333
Jan 4 - Jan 5, 2026
Total with taxes and fees
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
TV, fireplace, books
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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, (102)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
$380 nightly
The price is $435
Jan 6 - Jan 7, 2026
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Exterior
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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, (116)
"Comfortable and terrific location"
United States
Barry L.
$428 nightly
The price is $490
Jan 5 - Jan 6, 2026
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
TV, books
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Chatham
8.6 out of 10, Excellent, (26)
"This was a very nice place to stay, the location was perfect. A short walk to town and centrally located on the Cape as a whole. This home had all of the amenities need for a comfortable stay."
United States
Jeffrey A.
$476 nightly
The price is $545
Jan 5 - Jan 6, 2026
Total with taxes and fees
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Sundeck
Riverview Resort

Riverview Resort

Riverview Resort
3.0 star property
Bass River
9.2 out of 10, Wonderful, (173)
"The staff was very helpful and upgraded us to a room with a view. The amenities were perfect. We definitely would go back there."
United States
John
$219 nightly
The price is $251
Jan 2 - Jan 3, 2026
Total with taxes and fees
Riverview Resort
Indoor pool, seasonal outdoor pool
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
$129 nightly
The price is $147
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
Outdoor dining
🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
$373 nightly
The price is $427
Dec 30 - Dec 31
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Pool
Cozy Large Home in Harwich with Patio near Wequassett Resort

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, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
$468 nightly
The price is $518
Jan 9 - Jan 10, 2026
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
Smart TV, books
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
West Brewster
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
$628 nightly
The price is $719
Jan 16 - Jan 17, 2026
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Exterior
Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
$420 nightly
The price is $465
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lovely House 5 Min to Beach with Deck, Grill, Garage
Exterior
Stylish 2nd floor Ocean Edge condo

Stylish 2nd floor Ocean Edge condo

Stylish 2nd floor Ocean Edge condo
Brewster
9.8 out of 10, Exceptional, (9)
"Great property. It looks like it was recently renovated and done really well. Convenient to the beaches and restaurants, and golf. We love Brewster. "
United States
Garret J.
$371 nightly
The price is $425
Dec 26 - Dec 27
Total with taxes and fees
Stylish 2nd floor Ocean Edge condo
On the beach
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (23)
"Lovely time!"
United States
Joan W.
$417 nightly
The price is $477
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sand Bar-Dog Friendly on Cooks Brook Beach
Smart TV, fireplace
The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (21)
"Lovely property, spacious and VERY clean..location is ideal..."
United States
Kathy M.
$431 nightly
The price is $493
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Pet-Friendly Surf Shack Hideaway on the Cove
Property grounds
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
$316 nightly
The price is $350
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Outdoor dining
Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (7)
"Overall, we had a really great stay. The home is in a quiet neighborhood & close to the beach. Everything was clean and as described in the listing. "
United States
Kallee M.
$435 nightly
The price is $498
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Smart TV, fireplace, books
Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod
South Yarmouth
10.0 out of 10, Exceptional, (12)
"Great stay!"
United States
Kevin B.
$475 nightly
The price is $544
Jan 7 - Jan 8, 2026
Total with taxes and fees
Modern Beach & Pond Getaway; Heart of Cape Cod
Property grounds
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Eastham
10.0 out of 10, Exceptional, (18)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
$432 nightly
The price is $494
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Outdoor dining
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
$482 nightly
The price is $552
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Smart TV
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Eastham
10.0 out of 10, Exceptional, (2)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
$576 nightly
The price is $659
Jan 6 - Jan 7, 2026
Total with taxes and fees
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Interior
The Nantucket Room Unit - #2

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
$203 nightly
The price is $224
Dec 28 - Dec 29
Total with taxes and fees
The Nantucket Room Unit - #2
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

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Charming, cozy , clean! "
Erica 1-night trip
Posted 3 days ago
Chatham Wayside Inn

Price trends for vacation rentals in Chatham

Less expensive
More expensive
Next month
December
September
$314
Month
Price
January
$314
February
$418
March
$319
April
$394
May
$414
June
$484
July
$506
August
$510
September
$540
October
$409
November
$422
December
$312
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Chatham. Select dates and complete search for nightly totals inclusive of taxes and fees.

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 $204 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?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: Visitors give good reviews to this Chatham vacation home rental, which is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Gallery Antonia and Monomoy Theatre, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod Beaches 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.