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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Old 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, 7, (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 ￥43,036
￥54,796 total
includes taxes & fees
Sep 28 - Sep 29
BLUSH: Boutique TINY home*private spa*walk to town
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, 7, (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.
The price is ￥10,753
￥31,951 total
includes taxes & fees
Sep 16 - Sep 17
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, 1143, (1,143 reviews)
"Clean & comfortable stay"
United States
Robert
The price is ￥12,227
￥17,090 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
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, 174, (174 reviews)
"Great little place."
United States
Kim
The price is ￥18,043
￥20,209 total
includes taxes & fees
Sep 16 - Sep 17
Micosta Leisure Inn
A modern building with a wooden deck and a door.

5. 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, 5, (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 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, 3, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is ￥39,785
￥50,585 total
includes taxes & fees
Sep 22 - Sep 23
Sugar Shack - 300 square feet of pure sweetness.
A camping setup with a metal chair and a table by a river in a forest.

7. 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, 13, (13 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 ￥30,722
￥52,473 total
includes taxes & fees
Sep 20 - Sep 21
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden deck with a staircase leading to a covered porch area.

8. All comforts of home

All comforts of home
Hudson
9.6 out of 10, 59, (59 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,069
￥20,316 total
includes taxes & fees
Sep 16 - Sep 17
All comforts of home
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, 2644, (2,644 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is ￥14,614
￥18,009 total
includes taxes & fees
Sep 17 - Sep 18
Vacation Village in the Berkshires
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, 18, (18 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is ￥19,201
￥28,133 total
includes taxes & fees
Sep 16 - Sep 17
Taborton Harvest Boulder Pines Cabin in the woods
Cherry Plain State Park with a sandy beach, people relaxing, and a lake.

11. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, 4, (4 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 ￥16,897
￥36,355 total
includes taxes & fees
Sep 16 - Sep 17
Berkshires Apartment at the Stephentown Hotel
A white two-story house with a porch, surrounded by trees and a hill.

12. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, 5, (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 ￥34,409
￥73,549 total
includes taxes & fees
Oct 7 - Oct 8
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A backyard with a fire pit, wooden deck, and string lights.

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

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, 3, (3 reviews)
"Very nice. Will rent again!"
United States
Kathy A.
The price is ￥28,725
￥55,742 total
includes taxes & fees
Sep 16 - Sep 17
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A wooden deck with a staircase leading to a covered porch area.

14. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, 36, (36 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,313
￥19,992 total
includes taxes & fees
Sep 20 - Sep 21
All the comforts of home
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, 7, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,035
￥86,106 total
includes taxes & fees
Sep 21 - Sep 22
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A snow-covered outdoor area with a fire pit, tables, and chairs.

16. 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, 6, (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 ￥15,346
￥35,156 total
includes taxes & fees
Sep 16 - Sep 17
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

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, 7, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is ￥38,095
￥82,384 total
includes taxes & fees
Sep 29 - Sep 30
NEW RENO Historic Creamery in Berkshires w/hot tub
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

18. 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, 6, (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 ￥16,590
￥36,719 total
includes taxes & fees
Sep 17 - Sep 18
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
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 ￥34,409
￥85,125 total
includes taxes & fees
Sep 21 - Sep 22
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

20. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, 3, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
Gorgeous Mountain View Suite Ski On/Off At Jiminy - 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

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

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

10/10 Excellent
"Pristine and new. Staff was friendly and the breakfast was delicious."
SUSAN 1-night trip
Posted 4 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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:

  • View our selection of featured holiday rentals in Old Chatham
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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. Queechy Lake and Martin Van Buren National Historic Site 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.