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

Old Chatham Vacation Rentals

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Our top choices for Old Chatham vacation rentals

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is CA $99
CA $275 total
includes taxes & fees
Nov 10 - Nov 11
NEW RENO - Chalet-style farm loft near Tanglewood

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,266 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is CA $108
CA $153 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge

3. 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.
The price is CA $355
CA $818 total
includes taxes & fees
Nov 16 - Nov 17
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

4. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (196 reviews)
"Great stay"
United States
George
The price is CA $150
CA $168 total
includes taxes & fees
Nov 12 - Nov 13
Micosta Leisure Inn

5. 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.
The price is CA $380
CA $465 total
includes taxes & fees
Nov 15 - Nov 16
Sugar Shack - 300 square feet of pure sweetness.

6. 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, (18 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.
The price is CA $283
CA $465 total
includes taxes & fees
Nov 10 - Nov 11
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

7. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,838 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is CA $114
CA $142 total
includes taxes & fees
Nov 10 - Nov 11
Vacation Village in the Berkshires

8. 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, (8 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.
The price is CA $366
CA $449 total
includes taxes & fees
Nov 10 - Nov 11
BLUSH: Boutique TINY home*private spa*walk to town

9. 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.
The price is CA $101
CA $276 total
includes taxes & fees
Nov 12 - Nov 13
Berkshires Apartment at the Stephentown Hotel

10. 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.
The price is CA $232
CA $579 total
includes taxes & fees
Nov 10 - Nov 11
1789 Shaker Farmhouse in Berkshires/Hudson Valley

11. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (65 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
The price is CA $139
CA $174 total
includes taxes & fees
Nov 10 - Nov 11
All comforts of home

12. 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.
The price is CA $150
CA $187 total
includes taxes & fees
Nov 10 - Nov 11
All the comforts of home

13. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (20 reviews)
"Good location for sightseeing around the north east and New England"
United States
Nathan
The price is CA $159
CA $227 total
includes taxes & fees
Nov 10 - Nov 11
Taborton Harvest Boulder Pines Cabin in the woods

14. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Near Hudson With New Private Sauna

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

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is CA $136
CA $300 total
includes taxes & fees
Nov 10 - Nov 11
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

16. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is CA $136
CA $300 total
includes taxes & fees
Nov 10 - Nov 11
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

17. 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)
"It was a great stay! Centrally located in the Berkshire, very comfortable beds, amazing amenities!"
United States
Molly K.
The price is CA $405
CA $784 total
includes taxes & fees
Dec 9 - Dec 10
NEW RENO Historic Creamery in Berkshires w/hot tub

18. Simple & Central 1BD/1BA Fl 3 Apt @DowntownAlbany

Simple & Central 1BD/1BA Fl 3 Apt @DowntownAlbany
Pastures
9.4 out of 10, Exceptional, (3 reviews)
"We loved the stay so we extended our stay! Very clean, the host always reply’s making any problems easy to fix, very cozy and cheaper than a hotel!"
United States
Sarah
The price is CA $102
CA $217 total
includes taxes & fees
Nov 10 - Nov 11
Simple & Central 1BD/1BA Fl 3 Apt @DowntownAlbany

19. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is CA $136
CA $300 total
includes taxes & fees
Nov 10 - Nov 11
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

20. 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
The price is CA $359
CA $830 total
includes taxes & fees
Nov 10 - Nov 11
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

Find out more about Old Chatham

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Chatham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.