Chatham Vacation Rentals

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Our top choices for Chatham vacation rentals

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, (121 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
$526 nightly
The price is $602
Jun 2 - Jun 3
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Luxury Chatham Retreat. Walk to Main St & Beach

Luxury Chatham Retreat. Walk to Main St & Beach
Chatham
10.0 out of 10, Exceptional, (1 review)
"Beautiful house in a great location in Chatham! Walking distance to shops and restaurants. The house was well-stocked with everything we needed and the beds were so comfortable. We really enjoyed our stay here!"
United States
Maggie K.
$677 nightly
The price is $775
Jun 1 - Jun 2
Total with taxes and fees
Luxury Chatham Retreat. Walk to Main St & Beach

Town Center-Limited June, Aug, Sept Dates Still Open-2026 Total Renovation

Town Center-Limited June, Aug, Sept Dates Still Open-2026 Total Renovation
Chatham
$759 nightly
The price is $869
Jun 16 - Jun 17
Total with taxes and fees
Town Center-Limited June, Aug, Sept Dates Still Open-2026 Total Renovation

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.
$513 nightly
The price is $587
Jun 1 - Jun 2
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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.
$447 nightly
The price is $512
May 31 - Jun 1
Total with taxes and fees
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

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.
$1,430 nightly
The price is $1,637
May 31 - Jun 1
Total with taxes and fees
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
$317 nightly
The price is $363
May 31 - Jun 1
Total with taxes and fees
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
$635 nightly
The price is $727
May 31 - Jun 1
Total with taxes and fees
Coastal Haven in West Dennis -15

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Yarmouth
$385 nightly
The price is $441
Jun 1 - Jun 2
Total with taxes and fees
Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

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, (61 reviews)
"Clean, great location. "
United States
Peter G.
$323 nightly
The price is $370
Jun 1 - Jun 2
Total with taxes and fees
On Town Cove with salt water access! Kayaks and paddle board available for use!

Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail

Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail
South Wellfleet
10.0 out of 10, Exceptional, (68 reviews)
"We really enjoyed the location and deck."
United States
Donald W.
$737 nightly
The price is $844
Jun 5 - Jun 6
Total with taxes and fees
Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail

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.
$421 nightly
The price is $482
May 31 - Jun 1
Total with taxes and fees
Edgewood on Campground Beach/Steps to the Sand

🐚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.
$347 nightly
The price is $397
Jun 1 - Jun 2
Total with taxes and fees
🐚The Bay Cottage on Thumpertown Beach

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 30 - May 31
Total with taxes and fees
Family Cottage Close to Beach!!

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, (113 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
$274 nightly
The price is $314
Jun 5 - Jun 6
Total with taxes and fees
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Eastham
10.0 out of 10, Exceptional, (45 reviews)
"Great place, very clean. Host was accessible and accommodating. "
United States
Christopher M.
$863 nightly
The price is $988
May 31 - Jun 1
Total with taxes and fees
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

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
Jun 11 - Jun 12
Total with taxes and fees
6 Mi to Beach: Home w/ Deck in Brewster!

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, (113 reviews)
"Just as we expected we were greeted with happy pup barks and smiling faces.Our stay in Mike and Joe’s home was extremely comfortable. "
United States
Michael C.
$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

The Breeze on Minister's Pond

The Breeze on Minister's Pond
Eastham
10.0 out of 10, Exceptional, (25 reviews)
"The Breeze is the cutest, warmest, comfiest home. We thoroughly enjoyed our stay and will definitely book again!"
United States
MelanieC
$412 nightly
The price is $471
Jun 12 - Jun 13
Total with taxes and fees
The Breeze on Minister's Pond

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
Bass River
10.0 out of 10, Exceptional, (108 reviews)
"Nice quiet neighborhood but close to a lot of different attractions. The home was perfect for our needs."
United States
Ryan T.
$651 nightly
The price is $745
May 30 - May 31
Total with taxes and fees
Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
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 $159 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 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 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 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.