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
10.0 out of 10, Exceptional, (1 review)
"Lovely spot on the water!"
United States
Elizabeth T.
The price is CA $205
CA $770 total
includes taxes & fees
Jun 24 - Jun 25
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)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is CA $335
CA $1,019 total
includes taxes & fees
Jul 14 - Jul 15
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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.
The price is CA $569
CA $1,262 total
includes taxes & fees
Jun 24 - Jun 25
Luxury Chatham Retreat. Walk to Main St & Beach

Spacious 4BR house in perfect Chatham with AC

Spacious 4BR house in perfect Chatham with AC
Chatham
Spacious 4BR house in perfect Chatham with AC

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Chatham
10.0 out of 10, Exceptional, (135 reviews)
"gorgeous property - truly stunning view!"
United States
Kelly Z.
The price is CA $2,477
CA $4,071 total
includes taxes & fees
Jul 18 - Jul 19
Waterfront Chatham Village, Short Walk to Town & Lighthouse 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, (116 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is CA $180
CA $456 total
includes taxes & fees
Jun 25 - Jun 26
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

🌊The Ocean Cottage on Thumpertown Beach

🌊The Ocean Cottage on Thumpertown Beach
Eastham
9.4 out of 10, Exceptional, (9 reviews)
"We absolutely loved the place and the location right near Thumpertown Beach was perfect!"
United States
Jeff P.
🌊The Ocean Cottage on Thumpertown Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Dennis Port
The price is CA $156
CA $689 total
includes taxes & fees
Jun 29 - Jun 30
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Eastham, Cape Cod - Town Cove Waterfront

Eastham, Cape Cod - Town Cove Waterfront
Eastham
9.0 out of 10, Wonderful, (100 reviews)
"Awesome location, private and peaceful."
United States
Kathy D.
Eastham, Cape Cod - Town Cove Waterfront

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis
Brewster
9.0 out of 10, Wonderful, (20 reviews)
"Facility was excellent"
United States
Joe K.
The price is CA $192
CA $790 total
includes taxes & fees
Jun 25 - Jun 26
Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

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)
"We loved the house. Simple and comfortable, exactly what we needed to relax. thank you."
United States
Michael M.
The price is CA $270
CA $987 total
includes taxes & fees
Jun 29 - Jun 30
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (24 reviews)
The price is CA $149
CA $687 total
includes taxes & fees
Jun 25 - Jun 26
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Driftwood Cottages - Crab

Driftwood Cottages - Crab
Eastham
The price is CA $417
CA $1,338 total
includes taxes & fees
Jul 1 - Jul 2
Driftwood Cottages - Crab

Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining
Dennis Port
9.0 out of 10, Wonderful, (66 reviews)
"Great location and very nice apartment"
United States
Phil M.
The price is CA $318
CA $902 total
includes taxes & fees
Jul 6 - Jul 7
Quaint condo near private beach access with fireplace - close to dining

🐳 The Whale Song - Dog-Friendly Studio

🐳 The Whale Song - Dog-Friendly Studio
Eastham
9.6 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay very much "
United States
Gregg P.
The price is CA $174
CA $466 total
includes taxes & fees
Jun 24 - Jun 25
🐳 The Whale Song - Dog-Friendly Studio

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 $202
CA $514 total
includes taxes & fees
Jun 28 - Jun 29
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Dennis Beach House - Walk to Beach - Pet Friendly

Dennis Beach House - Walk to Beach - Pet Friendly
Dennis
8.0 out of 10, Very good, (10 reviews)
"Very cozy and quite neighborhood felt right at home."
United States
John S.
The price is CA $535
CA $977 total
includes taxes & fees
Jun 28 - Jun 29
Dennis Beach House - Walk to Beach - Pet Friendly

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Yarmouth
The price is CA $287
CA $667 total
includes taxes & fees
Jun 29 - Jun 30
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
10.0 out of 10, Exceptional, (193 reviews)
"Good location, pet friendly and clean"
United States
Megan R.
The price is CA $191
CA $526 total
includes taxes & fees
Jul 6 - Jul 7
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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.

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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?

Cape Cod's "Beach Rose": Visitors like this Chatham vacation home rental. It offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chatham?

With 282 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 Caleb Nickerson House, 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.