Chatham Vacation Rentals from $101: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Chatham has to offer?

Spacious rustic house in Chatham, NY : This Chatham vacation home rental offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

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Our top choices for Chatham vacation rentals

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jim S.

$338 nightly

Jun 10 - Jun 11

Total with taxes and fees

Sugar Shack - 300 square feet of pure sweetness.

Chatham

Sue G.

$327 nightly

Jun 23 - Jun 24

Total with taxes and fees

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

$499 nightly

Jun 11 - Jun 12

Total with taxes and fees

BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

jack h.

$282 nightly

Jun 15 - Jun 16

Total with taxes and fees

Huttopia Berkshires

Williamstown

GEORGINA

$91 nightly

Jun 10 - Jun 11

Total with taxes and fees

Private Yacht on Catskill Creek

Catskill

Yannie C.

$253 nightly

Jun 10 - Jun 11

Total with taxes and fees

Beautiful Yacht on Catskill Creek

Catskill

Amy G.

$288 nightly

Jun 11 - Jun 12

Total with taxes and fees

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Sherwin

$218 nightly

Jul 9 - Jul 10

Total with taxes and fees

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Top Chatham Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"rented for 2 nights. Apt was clean and climate control worked as expected. Nicely equipped location is good."

Country Inn & Suites by Radisson, Downtown Albany New York

2/10 Terrible

"The room was incredibly dirty. The floors had water stains, and the bathroom was barely cleaned. Water stains were visible everywhere, even the toilet was gross. I stayed for two nights, and my room was never cleaned, and new towels weren’t provided. The hotel was extremely noisy. Guests were inconsiderate and didn’t seem to be aware of the time or that other guests were around. I couldn’t sleep a single night that I decided to leave at 6 AM. I rang the bell to check out, but no staff came. I just dropped my keys in the front and left. The staff was never around, and the elevators took forever, even though no one was using them. The hotel also had a very unpleasant smell. I would not recommend staying at this hotel at all. It’s absolutely filthy."

Spark by Hilton West Coxsackie

10/10 Excellent

"There was nothing I can complain about the room beautiful clean very comfortable very relaxing. I might add wonderful. They took care of me right away gave me a first floor and accommodated me and helped me with another problem. I needed to get closer to my venue where the wedding was help. It’s very helpful thank you so much."

Berkshires Untold

10/10 Excellent

"The hotel was beautiful. My room was very nice exactly what I needed. The decor was very inviting and the bathroom was amazingly beautiful as well as the lounge and grounds of the property. My only one wish was that there was coffee in the room. Although you just had to walk to the lobby to get coffee in the morning, you had to get up and get dressed first which would have been more convenient if coffee was already in the room."

The Red Lion Inn

8/10 Good

"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."

Vacation Village in the Berkshires

10/10 Excellent

"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent value for the money. Friendly staff. I got a one-bdrm condo for the price of a standard hotel. No grocery atores nearby some come with supplies if you plan to cook."

The Yankee Inn

10/10 Excellent

"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub for the many surrounding activities--it's slightly over an hour drive to Hartford, and I was happy to leave the hustle and bustle of the city and return to the beauty of the Berkshires. I was surrounded by nature, but a grocery store, pharmacy, laundromat, and stores were also a short distance down the road. An extensive daily breakfast selection surpassed any I've recently had, and I've done my fair share of traveling."

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 $101 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.

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Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

What are some of the best vacation home rentals that Chatham has to offer?

Spacious rustic house in Chatham, NY: This Chatham vacation home rental offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Chatham?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like The Bookstore, or get outside and enjoy nature at Queechy Lake. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.

Chatham Vacation Rentals

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Check prices for these dates

Our top choices for Chatham vacation rentals

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Sugar Shack - 300 square feet of pure sweetness.

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

BLUSH: Boutique TINY home*private spa*walk to town

Huttopia Berkshires

Private Yacht on Catskill Creek

Beautiful Yacht on Catskill Creek

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

All comforts of home

Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Micosta Leisure Inn

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

All the comforts of home

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Catskill Stay w/ Deck & Fire Pit

Charming Cottage in the Heart of Catskill & Pet Friendly

Modern Luxurious Cabin, Catskills - The Tiny Nook

Vacation Village in the Berkshires

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Berkshire Mountain Lodge

Find out more about Chatham

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BLUSH: Boutique TINY homeprivate spawalk to town