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
The price is CA $168
CA $704 total
includes taxes & fees
May 18 - May 19
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 CA $324
CA $782 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 CA $129
CA $682 total
includes taxes & fees
May 18 - May 19
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 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 CA $1,296
CA $2,278 total
includes taxes & fees
May 18 - May 19
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 CA $197
CA $499 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 CA $271
CA $666 total
includes taxes & fees
May 18 - May 19
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 CA $278
CA $643 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 CA $413
CA $1,043 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 CA $433
CA $1,124 total
includes taxes & fees
May 18 - May 19
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 CA $606
CA $1,243 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 CA $965
CA $1,761 total
includes taxes & fees
May 18 - May 19
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 CA $445
CA $969 total
includes taxes & fees
May 18 - May 19
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 CA $206
CA $540 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 CA $270
CA $776 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
The price is CA $151
CA $601 total
includes taxes & fees
May 26 - May 27
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 CA $208
CA $603 total
includes taxes & fees
May 18 - May 19
🦀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 CA $464
CA $685 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 CA $557
CA $1,358 total
includes taxes & fees
May 18 - May 19
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 CA $299
CA $342 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.
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Top Chatham Hotel Reviews

Find out more about Chatham

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chatham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.