A city street with buildings, parked cars, and solar panels.

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chatham vacation rentals

A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

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

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$269 nightly
The price is $303
Sep 29 - Sep 30
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
$290 nightly
The price is $325
Sep 28 - Sep 29
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

3. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"This place was better than the photos. Everything was well planned out and extremely comfortable. The host was very attentive with great information about the area. Would definitely recommend."
United States
Lori S.
$279 nightly
The price is $315
Oct 1 - Oct 2
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
A modern building with a wooden deck and a door.

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
$485 nightly
The price is $543
Sep 28 - Sep 29
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (178 reviews)
"Great little place."
United States
Kim
$113 nightly
The price is $127
Oct 1 - Oct 2
Total with taxes and fees
Micosta Leisure Inn
A wooden deck with a staircase leading to a covered porch area.

6. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (60 reviews)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Oct 1 - Oct 2
Total with taxes and fees
All comforts of home
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,156 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
A wooden deck with a staircase leading to a covered porch area.

8. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
$126 nightly
The price is $141
Oct 1 - Oct 2
Total with taxes and fees
All the comforts of home
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

9. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (309 reviews)
"Excellent place"
United States
Yeudin
$201 nightly
The price is $217
Oct 27 - Oct 28
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A backyard with a fire pit, wooden deck, and string lights.

10. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
$307 nightly
The price is $344
Sep 30 - Oct 1
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

11. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
$200 nightly
The price is $202
Sep 28 - Sep 29
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

12. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
$320 nightly
The price is $358
Sep 28 - Sep 29
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
A spacious living room with a dining area, a kitchen, and a large window.

13. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
$215 nightly
The price is $217
Sep 29 - Sep 30
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

14. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (30 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
$149 nightly
The price is $167
Sep 28 - Sep 29
Total with taxes and fees
Catskill Cottage Walk to Downtown & River Views
A hot tub under a wooden pergola with a natural, wooded backdrop.

15. Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Ravena
8.0 out of 10, Very good, (2 reviews)
"The host was very friendly. We had a great time."
United States
Richard H.
$200 nightly
The price is $216
Oct 26 - Oct 27
Total with taxes and fees
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

16. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.6 out of 10, Exceptional, (5 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
$125 nightly
The price is $140
Oct 11 - Oct 12
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A dining area with a table set for two, a vase with flowers, and a bottle of wine.

17. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (17 reviews)
"Melissa was very welcoming and attentive during my stay. The boat was lovely and well maintained."
United States
Marcello C.
$226 nightly
The price is $253
Sep 28 - Sep 29
Total with taxes and fees
Charming Yacht on Catskill Creek
A wooden cabin with a porch, a grill, and a flower planter.

18. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
$320 nightly
The price is $358
Sep 28 - Sep 29
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

19. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
$170 nightly
The price is $190
Sep 28 - Sep 29
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

20. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,678 reviews)
"Love this place for a weekend getaway."
United States
Jacob
$122 nightly
The price is $136
Sep 28 - Sep 29
Total with taxes and fees
Vacation Village in the Berkshires
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"It was a well appointed suite with kitchen, dining area, living room with a fireplace and the bedroom and a nice quiet corner of the property. I did sit out on the balcony and watch the sun go down and I had the best night sleep. I’ve had in a long time I would definitely go back. I didn’t use any of the amenities that they charge extra for, but because I was traveling, it was nice to just have a quiet night in."
Rachel Elion 1-night trip
Posted 7 hours ago
Vacation Village in the Berkshires

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 $121 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

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?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chatham?

With 11 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 Bousquet Ski Area, or get outside and enjoy nature at Kinderhook 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.