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 kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

1. 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)
"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 ￥11,050
￥32,480 total
includes taxes & fees
Oct 6 - Oct 7
NEW RENO - Chalet-style farm loft near Tanglewood
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, (1,174 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is ￥13,532
￥18,641 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Mountain Lodge
A modern building with a wooden deck and a door.

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.
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.

4. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (180 reviews)
"Great little place."
United States
Kim
The price is ￥15,761
￥17,650 total
includes taxes & fees
Oct 27 - Oct 28
Micosta Leisure Inn
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

5. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,709 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is ￥13,615
￥16,940 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

6. 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 ￥39,305
￥50,023 total
includes taxes & fees
Oct 6 - Oct 7
Sugar Shack - 300 square feet of pure sweetness.
A bedroom with a wooden bed, floral bedding, a nightstand with a lamp, and a window with a view of trees.

7. 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.
The price is ￥19,731
￥28,910 total
includes taxes & fees
Oct 6 - Oct 7
Taborton Harvest Boulder Pines Cabin in the woods
A camping setup with a metal chair and a table by a river in a forest.

8. 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.
The price is ￥31,570
￥53,922 total
includes taxes & fees
Oct 6 - Oct 7
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

9. 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.
The price is ￥39,305
￥50,023 total
includes taxes & fees
Oct 6 - Oct 7
BLUSH: Boutique TINY home*private spa*walk to town
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

10. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is ￥15,627
￥34,992 total
includes taxes & fees
Oct 6 - Oct 7
Berkshires Apartment at the Stephentown Hotel
A white two-story house with a porch, surrounded by trees and a hill.

11. 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 ￥32,044
￥74,916 total
includes taxes & fees
Oct 7 - Oct 8
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden deck with a staircase leading to a covered porch area.

12. 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
The price is ￥15,485
￥20,877 total
includes taxes & fees
Oct 13 - Oct 14
All comforts of home
A wooden deck with a staircase leading to a covered porch area.

13. 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 ￥16,764
￥22,312 total
includes taxes & fees
Oct 7 - Oct 8
All the comforts of home
A living room with a brown sofa, a glass coffee table, a dark wooden dresser, and a green plant.

14. 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.
The price is ￥14,064
￥27,633 total
includes taxes & fees
Oct 8 - Oct 9
Chic Madison Parkview
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

15. 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, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,782
￥88,483 total
includes taxes & fees
Oct 6 - Oct 7
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.

16. 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
The price is ￥43,882
￥90,454 total
includes taxes & fees
Oct 27 - Oct 28
NEW RENO Historic Creamery in Berkshires w/hot tub
A spacious room with a wooden ceiling, large windows, and a chandelier.

17. 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.
The price is ￥67,086
￥115,622 total
includes taxes & fees
Oct 6 - Oct 7
Luxury Barn Retreat — All-Season Escape Awaits!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

18. ★SPACIOUS 1BR Apt w/ Character 10ft Ceilings W/D!★

★SPACIOUS 1BR Apt w/ Character 10ft Ceilings W/D!★
Mansion
8.6 out of 10, Excellent, (10 reviews)
"A charming one bedroom near the cathedral and New York State museum. We enjoyed our stay!"
United States
Michael C.
The price is ￥18,468
￥36,311 total
includes taxes & fees
Oct 6 - Oct 7
★SPACIOUS 1BR Apt w/ Character 10ft Ceilings W/D!★
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

19. 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 ￥35,358
￥87,474 total
includes taxes & fees
Oct 6 - Oct 7
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A snow-covered outdoor area with a fire pit, tables, and chairs.

20. 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.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
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

Search for holiday rentals in Old Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Chatham using one of the methods below:

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Look no further and take a look at our great range of rental properties in Old Chatham!

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.