A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Chatham vacation rentals

Indoor spa tub

1. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (143 reviews)
"Clean, good activities for the kids and pools were nice"
United States
Jim
$219 nightly
The price is $251
Sep 24 - Sep 25
Total with taxes and fees
Brewster Green Resort
House (3 Bedrooms) | Front of property

2. 6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
$603 nightly
The price is $690
Sep 20 - Sep 21
Total with taxes and fees
6 Mi to Beach: Home w/ Deck in Brewster!
Living room

3. Thompson House Cape Cod

Thompson House Cape Cod
3.0 star property
South Yarmouth
$920 nightly
The price is $1,053
Oct 10 - Oct 11
Total with taxes and fees
Thompson House Cape Cod
Indoor pool

4. The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (268 reviews)
"P Indoor pool and hot tub loved and the outdoor Shack was great"
United States
BELKIS
$136 nightly
The price is $155
Sep 14 - Sep 15
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
Miscellaneous

5. Sal's Place

Sal's Place
2.0 star property
Hyannis
$650 nightly
The price is $727
Sep 15 - Sep 16
Total with taxes and fees
Sal's Place
Cottage (2 Bedrooms) | Interior

6. 1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very Good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
$318 nightly
The price is $364
Oct 2 - Oct 3
Total with taxes and fees
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
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

Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"Clean very nice staff Beautiful breakfast our stay could not have been better thank you so much"
James 3-night trip
Posted 12 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG

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 $155 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.

Explore a world of travel with Expedia

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": You might want to consider this vacation rental near Chatham, which 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 276 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 Chatham Railroad Museum and Chatham Drama Guild, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod Beaches 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.