A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Old Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Old Chatham vacation rentals

A modern building with a wooden deck and a door.

1. 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.
$539 nightly
The price is $604
Oct 12 - Oct 13
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,188 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
$115 nightly
The price is $128
Nov 8 - Nov 9
Total with taxes and fees
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,715 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

4. 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.
$294 nightly
The price is $332
Oct 13 - Oct 14
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.

5. 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.
$307 nightly
The price is $344
Oct 12 - Oct 13
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

6. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (185 reviews)
"Great little place."
United States
Kim
$113 nightly
The price is $127
Oct 13 - Oct 14
Total with taxes and fees
Micosta Leisure Inn
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

7. 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.
$304 nightly
The price is $343
Nov 2 - Nov 3
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
A spacious room with a wooden ceiling, large windows, and a chandelier.

8. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
$659 nightly
The price is $738
Oct 13 - Oct 14
Total with taxes and fees
Luxury Barn Retreat — All-Season Escape Awaits!
A white two-story house with a porch, surrounded by trees and a hill.

9. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
$495 nightly
The price is $502
Nov 2 - Nov 3
Total with taxes and fees
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden cabin with a porch, a door, and a window.

10. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (18 reviews)
"This was a dash away and perfect! "
United States
Linda R.
$153 nightly
The price is $169
Oct 11 - Oct 12
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

11. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (8 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
$509 nightly
The price is $565
Oct 12 - Oct 13
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

12. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
$566 nightly
The price is $574
Oct 27 - Oct 28
Total with taxes and fees
NEW RENO Historic Creamery in Berkshires w/hot tub
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

13. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
Oct 12 - Oct 13
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

14. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
$214 nightly
The price is $228
Oct 12 - Oct 13
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
A wooden deck with a staircase leading to a covered porch area.

15. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
$126 nightly
The price is $141
Oct 12 - Oct 13
Total with taxes and fees
All the comforts of home
A wooden deck with a staircase leading to a covered porch area.

16. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (63 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
$118 nightly
The price is $132
Oct 13 - Oct 14
Total with taxes and fees
All comforts of home
A patio with stone flooring, wicker chairs, and a red umbrella. A lake with a dock and a small boat is visible in the background.

17. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Averill Park
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
United States
KenD
$769 nightly
The price is $854
Oct 18 - Oct 19
Total with taxes and fees
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
A living room with a brown sofa, a glass coffee table, a dark wooden dresser, and a green plant.

18. Chic Madison Parkview

Chic Madison Parkview
Albany
9.4 out of 10, Exceptional, (53 reviews)
"Great location, easy access, amenities were great as well"
United States
Phoenix Hayden S.
$162 nightly
The price is $175
Oct 12 - Oct 13
Total with taxes and fees
Chic Madison Parkview
A backyard with a fire pit, wooden deck, and string lights.

19. 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.
$326 nightly
The price is $365
Oct 19 - Oct 20
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

20. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (7 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
$292 nightly
The price is $326
Oct 12 - Oct 13
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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 Old Chatham Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"The property was very well maintained and the room was very clean. Check in was quick and easy. The included breakfast was satisfying. Would stay here again."
James 1-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Old Chatham

Everything you need to know about Old 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 Old 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 Old Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old 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 Old 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 $127 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 Old Chatham rentals

At Expedia, we put the best Old 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 Old 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 Old 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 Old 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 Old Chatham?

Yes, we offer vacation rentals close to well known points of interest in Old Chatham, or you can choose a more remote option if you'd like a relaxing place to stay. Old Chatham is known for its museums.

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

Incredible Estate: Pool, Pond, Gym, Arcade, Trails & More: Labor Day Now Open!: Visitors like this Old Chatham vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 8 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 library so you can immerse yourself in your vacation.

How many vacation rentals will I find in Old Chatham?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Old Chatham stay.

What’s there to see and do in Old Chatham?

Enjoy the area's cultural attractions such as Shaker Museum and Library, or get outdoors into nature at a spot like Kinderhook Lake. Martin Van Buren National Historic Site and Art Omi International Arts Center - Fields Sculpture Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Old Chatham like?

Vacation rentals are privately owned properties you can book for several days or longer in Old Chatham. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.