Chatham Vacation Rentals

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Our top choices for Chatham vacation rentals

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 $143
CA $699 total
includes taxes & fees
May 19 - May 20
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
The price is CA $167
CA $696 total
includes taxes & fees
May 10 - May 11
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 $322
CA $777 total
includes taxes & fees
May 14 - May 15
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

🐚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.
The price is CA $202
CA $542 total
includes taxes & fees
May 12 - May 13
🐚The Bay Cottage on Thumpertown 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 $150
CA $598 total
includes taxes & fees
May 26 - May 27
Walk to Beaches & Dining: Classic Cape Cod Cottage

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 $269
CA $662 total
includes taxes & fees
May 10 - May 11
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)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is CA $206
CA $601 total
includes taxes & fees
May 12 - May 13
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Paradise Palm Unit - #4

Paradise Palm Unit - #4
Harwich
10.0 out of 10, Exceptional, (31 reviews)
"The property was quaint, perfect for a quick weekend getaway."
United States
Kylie S.
The price is CA $154
CA $286 total
includes taxes & fees
May 12 - May 13
Paradise Palm Unit - #4

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (53 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is CA $154
CA $286 total
includes taxes & fees
May 10 - May 11
The Nantucket Room Unit - #2

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (8 reviews)
"We went with a small group of friends and everything was amazing. The property is beautiful and well located. We had everything that we needed and the communication con the owner was good."
United States
Lourdes P.
The price is CA $212
CA $715 total
includes taxes & fees
May 26 - May 27
Sleeps 2-8/Soaking Tub/FirePit~Burrows

The Beachcomber Unit - #9

The Beachcomber Unit - #9
Harwich
9.8 out of 10, Exceptional, (18 reviews)
"We had an amazing time staying here, great location and it was very clean. "
United States
Mike B.
The price is CA $171
CA $308 total
includes taxes & fees
May 19 - May 20
The Beachcomber Unit - #9

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, (111 reviews)
"Cute space and perfect size for me and my small dog!"
United States
Amy F.
The price is CA $102
CA $349 total
includes taxes & fees
May 14 - May 15
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Harbor Hideaway Unit- #6

Harbor Hideaway Unit- #6
Harwich
9.8 out of 10, Exceptional, (18 reviews)
"Just as advertised — tucked away in a small neighborhood in Harwich. Easily accessible to great restaurants and beaches. Would book again in a heartbeat"
United States
Colin H.
The price is CA $154
CA $286 total
includes taxes & fees
May 11 - May 12
Harbor Hideaway Unit- #6

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.
The price is CA $262
CA $905 total
includes taxes & fees
May 20 - May 21
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

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

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is CA $159
CA $942 total
includes taxes & fees
May 14 - May 15
6 Mi to Beach: Home w/ Deck in Brewster!

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (11 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is CA $395
CA $942 total
includes taxes & fees
May 28 - May 29
Cozy Large Home in Harwich with Patio near Wequassett Resort

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 $268
CA $763 total
includes taxes & fees
May 10 - May 11
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

Castaway Cottage on the bay~Dog Friendly Too!

Castaway Cottage on the bay~Dog Friendly Too!
Eastham
9.8 out of 10, Exceptional, (14 reviews)
"Very good pet friendly house! "
United States
Sasha N.
The price is CA $233
CA $583 total
includes taxes & fees
May 11 - May 12
Castaway Cottage on the bay~Dog Friendly Too!

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 $205
CA $530 total
includes taxes & fees
Jun 1 - Jun 2
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Eastham
10.0 out of 10, Exceptional, (20 reviews)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is CA $247
CA $689 total
includes taxes & fees
May 25 - May 26
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
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 279 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.