Chatham Vacation Rentals

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Dec 5 - Dec 7

Vacation Rentals in Chatham

Fridge, microwave, oven, stovetop
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, (29)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
$280 nightly
The price is $320
Dec 1 - Dec 2
Total with taxes and fees
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Microwave, oven, stovetop, dishwasher
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, (101)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
$356 nightly
The price is $407
Nov 30 - Dec 1
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Beach nearby, sun loungers
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, (115)
"Comfortable and terrific location"
United States
Barry L.
$429 nightly
The price is $491
Nov 30 - Dec 1
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
2 bedrooms, iron/ironing board, WiFi, bed sheets
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.
$464 nightly
The price is $531
Dec 1 - Dec 2
Total with taxes and fees
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Exterior
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

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

4.0 star property
Chatham
10.0 out of 10, Exceptional, (21)
"It was a great experience. Beautiful house and location. Couldn’t have asked for anything better. "
United States
Anonymous traveler
$1,865 nightly
The price is $2,135
Dec 2 - Dec 3
Total with taxes and fees
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Fridge, microwave, oven, stovetop
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

4.0 star property
Chatham
10.0 out of 10, Exceptional, (18)
"Walk to all the shops and beaches. Quiet neighborhood, yet still in the heart of a beautiful Cape Cod home. Large table on a pretty porch that sits 12 people comfortably. Nice back yard. Very clean. Bill, the owner, was very responsive. You will enjoy your stay here!!"
United States
Diane C.
$1,456 nightly
The price is $1,666
Dec 2 - Dec 3
Total with taxes and fees
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Pool
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.
$372 nightly
The price is $426
Nov 29 - Nov 30
Total with taxes and fees
Stylish 2nd floor Ocean Edge condo
Fridge, microwave, oven, stovetop
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, (24)
"Beautiful, well appointed home ideally situated for exploring all the Cape has to offer from the Canal to Provincetown. Very enjoyable and relaxing vacation venue."
United States
Art T.
$583 nightly
The price is $667
Dec 9 - Dec 10
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Outdoor dining
🦀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 9 - Dec 10
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Outdoor dining
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis
10.0 out of 10, Exceptional, (176)
"Excellent property, super clean and location is perfect! "
United States
Karen B.
$273 nightly
The price is $313
Dec 1 - Dec 2
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Smart TV, fireplace
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.
$440 nightly
The price is $504
Nov 30 - Dec 1
Total with taxes and fees
The Pet-Friendly Surf Shack Hideaway on the Cove
Marina
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.
$441 nightly
The price is $488
Dec 1 - Dec 2
Total with taxes and fees
Lovely House 5 Min to Beach with Deck, Grill, Garage
Outdoor dining
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet
10.0 out of 10, Exceptional, (74)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
$379 nightly
The price is $433
Nov 30 - Dec 1
Total with taxes and fees
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Interior
Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Barnstable
9.4 out of 10, Exceptional, (11)
"Walk to Hyannis restaurants & bars. Walk to ferry. "
United States
Dina M.
$607 nightly
The price is $656
Nov 29 - Nov 30
Total with taxes and fees
Charming Hyannis 3 Bed 2 Bath
Fridge, microwave, oven, stovetop
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.
$453 nightly
The price is $518
Nov 30 - Dec 1
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Fridge, microwave, oven, stovetop
Coastal Haven in West Dennis

Coastal Haven in West Dennis

2.0 star property
Dennis
10.0 out of 10, Exceptional, (3)
"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"
United States
Edward R.
$600 nightly
The price is $653
Nov 29 - Nov 30
Total with taxes and fees
Coastal Haven in West Dennis
Beach
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
$305 nightly
The price is $338
Nov 30 - Dec 1
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Beach
Secluded-Entire 2nd floor Suite with Private Bath

Secluded-Entire 2nd floor Suite with Private Bath

Barnstable
10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
$139 nightly
The price is $159
Nov 29 - Nov 30
Total with taxes and fees
Secluded-Entire 2nd floor Suite with Private Bath
Outdoor dining
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.
$442 nightly
The price is $506
Dec 2 - Dec 3
Total with taxes and fees
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Interior
National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl

Eastham
10.0 out of 10, Exceptional, (8)
" We enjoyed our stay at the property. We loved the location. My only issue is two little things. First, the ppropettypropermanager is"
United States
Richard M.
$429 nightly
The price is $492
Dec 8 - Dec 9
Total with taxes and fees
National Seashore/Updated/Game Room~Blue Pearl
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

Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Yes, it was very nice. The staff was helpful. "
Mark 2-night trip
Posted 3 days ago
Hyannis Travel Inn

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 $313 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 277 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 Fish Pier and Chatham Lighthouse 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.