Chatham Vacation Rentals

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Our top choices for Chatham vacation rentals

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
$447 nightly
The price is $512
May 20 - May 21
Total with taxes and fees
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

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 reviews)
"We absolutely loved this house, very comfortable, well decorated and welcoming atmosphere. It was exactly what we needed for a weekend getaway. We will be back!"
United States
Margot C.
$431 nightly
The price is $493
May 20 - May 21
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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, (119 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
$505 nightly
The price is $578
May 26 - May 27
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Town Center-Summer Dates Still Available-Walk To Stores-2026 Total Renovation

Town Center-Summer Dates Still Available-Walk To Stores-2026 Total Renovation
Chatham
$757 nightly
The price is $866
Jun 16 - Jun 17
Total with taxes and fees
Town Center-Summer Dates Still Available-Walk To Stores-2026 Total Renovation

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!
Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Downtown Chatham Gem was perfect for our girls getaway weekend. Parked the cars and walked everywhere. The house was clean, beautifully decorated, and had everything we needed. Loved everything about it and we will definitely be back. "
United States
Claire S.
$1,447 nightly
The price is $1,656
May 20 - May 21
Total with taxes and fees
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Walk to Beaches & Dining: Classic Cape Cod Cottage

Walk to Beaches & Dining: Classic Cape Cod Cottage
3.0 star property
Dennis Port
$382 nightly
The price is $437
May 26 - May 27
Total with taxes and fees
Walk to Beaches & Dining: Classic Cape Cod Cottage

🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (11 reviews)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
$342 nightly
The price is $391
May 21 - May 22
Total with taxes and fees
🐚The Bay Cottage on Thumpertown Beach

Edgewood on Campground Beach/Steps to the Sand

Edgewood on Campground Beach/Steps to the Sand
Eastham
10.0 out of 10, Exceptional, (9 reviews)
"Cozy cottage right by the beach. Great area not for to restaurants and beaches. Would definitely stay again!"
United States
Melinda W.
$420 nightly
The price is $481
May 20 - May 21
Total with taxes and fees
Edgewood on Campground Beach/Steps to the Sand

🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (24 reviews)
"Perfect size home for a family of 4, welcoming and cozy! Having -All towels and linens and shampoo, body wash and conditioner all included made for a much easier stay! Highly recommend."
United States
Emily A.
$379 nightly
The price is $434
May 20 - May 21
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Yarmouth
$410 nightly
The price is $469
May 20 - May 21
Total with taxes and fees
Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Harwich
10.0 out of 10, Exceptional, (110 reviews)
"The hosts were so accommodating and lovely. The property is adorable and well appointed! Would stay again 100 percent. "
United States
rachel n.
$343 nightly
The price is $393
Jun 1 - Jun 2
Total with taxes and fees
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

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, (51 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
$533 nightly
The price is $610
May 20 - May 21
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (53 reviews)
"Very clean and comfortable stay! Highly recommend "
United States
Karen R.
$190 nightly
The price is $209
May 20 - May 21
Total with taxes and fees
The Nantucket Room Unit - #2

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 reviews)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
$575 nightly
The price is $658
May 20 - May 21
Total with taxes and fees
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 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
May 20 - May 21
Total with taxes and fees
Family Cottage Close to Beach!!

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

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
$602 nightly
The price is $689
May 29 - May 30
Total with taxes and fees
6 Mi to Beach: Home w/ Deck in Brewster!

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.6 out of 10, Excellent, (8 reviews)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
$451 nightly
The price is $499
May 20 - May 21
Total with taxes and fees
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

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
9.6 out of 10, Exceptional, (112 reviews)
"Cute space and perfect size for me and my small dog!"
United States
Amy F.
$293 nightly
The price is $336
Jun 5 - Jun 6
Total with taxes and fees
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Gray Whale - 3 bedrm/2 bath/gameroom

Gray Whale - 3 bedrm/2 bath/gameroom
Eastham
10.0 out of 10, Exceptional, (3 reviews)
"very well appointed accommodations - great location - helpful amenities. would come back again!"
United States
Leonard
$521 nightly
The price is $596
May 20 - May 21
Total with taxes and fees
Gray Whale - 3 bedrm/2 bath/gameroom

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.6 out of 10, Excellent, (4 reviews)
"Perfect location for the ferry and some great restaurants. We walked everywhere. Super comfortable to relax after being gone all day. Bathroom was hotel quality. Great view from the deck. "
United States
Rose T.
$372 nightly
The price is $426
May 20 - May 21
Total with taxes and fees
Charming 3 bed room with magnificent views & large deck
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 $189 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.

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?

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches: Visitors give good reviews to this Chatham vacation home rental, which is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Chatham?

With 278 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 Chatham Railroad Museum, whereas Chatham Lighthouse Beach and Cape Cod Beaches are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod National Seashore 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.