Chatham Vacation Rentals

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Vacation Rentals in Chatham

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham
10.0 out of 10, Exceptional, (39)
"Gorgeous well stocked home accommodated our large family in style!! Plenty of Beach & Pool towels, beach chairs, and kitchen appliances for all of our meals! Loved the house and Chatham! Walkable to beach, restaurants and shops. So Fun!"
United States
Kim K.
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham
8.2 out of 10, Very Good, (72)
"Great stay at this bright, airy, cozy cottage. We enjoyed coffee and happy hour on the deck overlooking the river and boats each day. Hated to leave!"
United States
Cathy S.
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham
10.0 out of 10, Exceptional, (114)
"Comfortable and terrific location"
United States
Barry L.
$429 nightly
The price is $491
Nov 19 - Nov 20
Total with taxes and fees
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
9.6 out of 10, Exceptional, (99)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
$357 nightly
The price is $408
Nov 18 - Nov 19
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

See the World Cup AND Enjoy a Chatham Vacation June 2026

Chatham
10.0 out of 10, Exceptional, (100)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
See the World Cup AND Enjoy a Chatham Vacation June 2026

Holly Tree Resort

3.0 star property
West Yarmouth
9.0 out of 10, Wonderful, (366)
"We had a great stay!"
United States
Shelly
Holly Tree Resort

Edgewater Beach Resort, a VRI resort

3.5 star property
Dennis Port
8.8 out of 10, Excellent, (291)
"Room was clean and the staff was great"
United States
Linda
Edgewater Beach Resort, a VRI resort

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (119)
"Super clean and a really large space! "
United States
Linda
$159 nightly
The price is $182
Nov 18 - Nov 19
Total with taxes and fees
Brewster Green Resort

Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Eastham
10.0 out of 10, Exceptional, (27)
"Heaven! Best spot on the end of cul de sac with stunning water views from all rooms, especially the outdoor deck. Clean, comfortable and nicely decorated. Great communication pre check-in and during stay. Did not want to leave! Look forward to future stay. "
United States
Kristin
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Riverview Resort

3.0 star property
Bass River
9.2 out of 10, Wonderful, (168)
"The room was big and very clean. The hotel is quaint and quiet. It does not have an elevator which could be an issue for some but we made it work. Overall a great place to stay. Very comfortable and inviting and we loved the amenities."
United States
Kathleen
Riverview Resort

The Cove at Yarmouth by VRI Americas

3.5 star property
West Yarmouth
9.2 out of 10, Wonderful, (326)
"First time staying here and i was impressed"
United States
Wayne
The Cove at Yarmouth by VRI Americas

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (232)
"I absolutely loved my stay at this charming cottage in Hyannis! The place was cozy, spotless, and beautifully maintained. A perfect mix of comfort and Cape Cod charm. The location was great, close to the beach and local shops, yet quiet enough to relax and unwind."
United States
Maria
Steps to the Ocean! Perfect Location!!!

beachfront cottage at Chases Ocean Grove

Dennis Port
9.6 out of 10, Exceptional, (33)
"Such a cool place! Just a few feet from the beach, we began and ended each day in the sand. The location is also great for traveling to all the cape cod hot spots. The cottage is really sweet and cozy— we hope to be back! "
United States
trisha d.
beachfront cottage at Chases Ocean Grove

Charming Waterview Victorian w/Cottages near beach, harbor & town

Wellfleet
9.8 out of 10, Exceptional, (53)
"Great location for bars, shops and restaurants. Property was perfect for large group. Main home is 150 years old, which gives it character, but also means updates are needed."
United States
Mike M.
Charming Waterview Victorian w/Cottages near beach, harbor & town

Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts

Eastham
10.0 out of 10, Exceptional, (222)
"Always a great place to stay!!!!"
United States
Christine J.
Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts

OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

Bass River
10.0 out of 10, Exceptional, (110)
"Great family time! Beautiful location right on the beach. "
United States
David A.
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Dennis
10.0 out of 10, Exceptional, (15)
"Perfect location for Mayflower and Corporation beach , lovely house and yard for small family gatherings . "
United States
Nancy R.
$629 nightly
The price is $720
Nov 20 - Nov 21
Total with taxes and fees
Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Walk To Beach - Comfortable 2BR Cottage

Dennis Port
9.6 out of 10, Exceptional, (35)
"My friend and I spent 3 nights here while we explored this area of Cape Cod and Martha’s Vineyard. Clean and had what we needed!"
United States
Jill B.
Walk To Beach - Comfortable 2BR Cottage

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Orleans
10.0 out of 10, Exceptional, (73)
"Great spot"
United States
Eugene P.
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

Dennis
9.4 out of 10, Exceptional, (117)
"Great choice. Location"
United States
Carol I.
Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!
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 $182 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?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This highly rated vacation home rental in Chatham is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. Another good choice for your trip to Chatham is Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK.

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 Monomoy Theatre, whereas Chatham Lighthouse Beach and Monomoy National Wildlife Refuge are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Fish Pier and Chatham Lighthouse 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.