Chatham Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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
The price is ¥19,366
¥81,227 total
includes taxes & fees
May 17 - May 18
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

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.
The price is ¥37,346
¥89,508 total
includes taxes & fees
May 18 - May 19
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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.
The price is ¥14,888
¥78,154 total
includes taxes & fees
May 17 - May 18
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

The Barn at Chatham Oaks

The Barn at Chatham Oaks
Chatham
9.6 out of 10, Exceptional, (9 reviews)
"My family had the best weekend in this beautiful home! I will book again."
United States
Erin W.
The price is ¥164,874
¥326,013 total
includes taxes & fees
May 17 - May 18
The Barn at Chatham Oaks

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.
The price is ¥149,581
¥262,944 total
includes taxes & fees
May 17 - May 18
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
The price is ¥22,648
¥57,520 total
includes taxes & fees
May 20 - May 21
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

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.
The price is ¥31,217
¥76,151 total
includes taxes & fees
May 17 - May 18
Edgewood on Campground Beach/Steps to the Sand

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Yarmouth
The price is ¥32,072
¥74,230 total
includes taxes & fees
May 18 - May 19
Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Classic Cape House Walking Distance to the Beach - Many recent upgrades

Classic Cape House Walking Distance to the Beach - Many recent upgrades
Chatham
9.8 out of 10, Exceptional, (20 reviews)
"Mary was a wonderful host. The house was clean, close to beach and communication was wonderful! A great, relaxing stay!!"
United States
Kathleen T.
The price is ¥47,514
¥119,274 total
includes taxes & fees
May 23 - May 24
Classic Cape House Walking Distance to the Beach - Many recent upgrades

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.
The price is ¥50,003
¥129,719 total
includes taxes & fees
May 17 - May 18
Family Cottage Close to Beach!!

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.
The price is ¥71,116
¥144,981 total
includes taxes & fees
Jun 5 - Jun 6
Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Harwich - Brewster Border
10.0 out of 10, Exceptional, (6 reviews)
"Lovely property with attentive hosts "
United States
marian t.
The price is ¥111,183
¥202,293 total
includes taxes & fees
May 17 - May 18
Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

Coastal Haven in West Dennis

Coastal Haven in West Dennis
Dennis
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay and relax, just a short walk to the beach and quick drive to great restaurants and activities. Highly recommend!!"
United States
Melissa J.
The price is ¥51,220
¥109,938 total
includes taxes & fees
May 17 - May 18
Coastal Haven in West Dennis

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.
The price is ¥23,811
¥62,315 total
includes taxes & fees
Jun 1 - Jun 2
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
Wellfleet
The price is ¥31,115
¥89,569 total
includes taxes & fees
May 20 - May 21
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

Walk to Beaches & Dining: Classic Cape Cod Cottage

Walk to Beaches & Dining: Classic Cape Cod Cottage
3.0 star property
Dennis Port
Walk to Beaches & Dining: Classic Cape Cod Cottage

🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (24 reviews)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is ¥24,107
¥68,917 total
includes taxes & fees
May 17 - May 18
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
Harwich
The price is ¥53,453
¥78,216 total
includes taxes & fees
May 21 - May 22
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

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, (44 reviews)
"Great place, very clean. Host was accessible and accommodating. "
United States
Christopher M.
The price is ¥64,144
¥156,434 total
includes taxes & fees
May 17 - May 18
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (130 reviews)
"Mike is the best. Very clean environment and family welcome"
United States
Catherine
The price is ¥34,456
¥39,435 total
includes taxes & fees
May 21 - May 22
Brewster Green Resort
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chatham Hotel Reviews

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

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.