A calm lake surrounded by dense evergreen trees and a few deciduous trees with autumn leaves.

East Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for East Chatham vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,043 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is ￥19,751
￥25,586 total
includes taxes & fees
Aug 30 - Aug 31
Berkshire Mountain Lodge
Exterior

2. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (163 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is ￥21,806
￥24,421 total
includes taxes & fees
Sep 1 - Sep 2
Micosta Leisure Inn
Coffee/tea maker, fridge, microwave, oven

3. 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 ￥15,774
￥37,895 total
includes taxes & fees
Aug 9 - Aug 10
NEW RENO - Chalet-style farm loft near Tanglewood
Lobby

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,505 reviews)
"I have been visiting this property for years and it is always great. Can’t beat it after a few days of adventure in the Berkshires"
United States
Brooks
The price is ￥16,603
￥20,275 total
includes taxes & fees
Aug 30 - Aug 31
Vacation Village in the Berkshires
Dining

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

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (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 ￥41,012
￥52,300 total
includes taxes & fees
Aug 6 - Aug 7
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

6. 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 ￥41,801
￥53,190 total
includes taxes & fees
Aug 19 - Aug 20
BLUSH: Boutique TINY home*private spa*walk to town
Exterior detail

7. 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, (4 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 ￥48,426
￥106,708 total
includes taxes & fees
Aug 25 - Aug 26
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ￥39,435
￥63,777 total
includes taxes & fees
Aug 9 - Aug 10
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Family Bungalow

9. Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (14 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ￥18,357
￥20,505 total
includes taxes & fees
Aug 23 - Aug 24
Huttopia Berkshires
Property grounds

10. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is ￥15,474
￥20,862 total
includes taxes & fees
Aug 9 - Aug 10
All comforts of home
Property grounds

11. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,752
￥22,297 total
includes taxes & fees
Aug 9 - Aug 10
All the comforts of home
House (3 Bedrooms) | Interior

12. 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 ￥35,334
￥87,413 total
includes taxes & fees
Aug 6 - Aug 7
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Coffee/tea maker, fridge, microwave, stovetop

13. 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, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ￥27,762
￥88,421 total
includes taxes & fees
Aug 6 - Aug 7
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

14. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is ￥19,718
￥28,891 total
includes taxes & fees
Aug 7 - Aug 8
Taborton Harvest Boulder Pines Cabin in the woods
Beach

15. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (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 ￥22,036
￥42,998 total
includes taxes & fees
Aug 10 - Aug 11
Berkshires Apartment at the Stephentown Hotel
Terrace/patio

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

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice. Will rent again!"
United States
Kathy A.
The price is ￥29,497
￥57,947 total
includes taxes & fees
Aug 16 - Aug 17
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Outdoor dining

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, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is ￥47,007
￥93,370 total
includes taxes & fees
Aug 6 - Aug 7
NEW RENO Historic Creamery in Berkshires w/hot tub
Outdoor spa tub

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

Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Ravena
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly. We had a great time."
United States
Richard H.
The price is ￥16,894
￥35,280 total
includes taxes & fees
Aug 6 - Aug 7
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Exterior

19. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 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 ￥42,590
￥87,906 total
includes taxes & fees
Sep 1 - Sep 2
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Pool

20. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
Mountain Getaway Suite Ski OnOff Jiminy Peak - 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 East Chatham Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. The breakfast is as good as any other hotel brand that offers breakfast. The shopping center is right next door within walking distance, with a few places to eat. It’s a great location also to get to anywhere in the area."
Zachary 2-night trip
Posted 4 hours ago
The Yankee Inn

Find out more about East Chatham

Search for holiday rentals in East Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in East 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 East Chatham!

Frequently asked questions

Can I find a vacation rental in East Chatham?

Yes, we have vacation rentals close to popular local attractions in East Chatham, or you can select a more secluded option if you'd like a relaxing place to stay.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of East Chatham is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in East Chatham?

Expedia has 8 vacation rentals for your stay in East Chatham.

What can I see and do in East Chatham?

Meizinger Lake and Hand Hollow Conservation Area are a couple of lovely local spots to get outside and enjoy nature. Hand Hollow State Forest and The Mac-Haydn Theatre are a couple of places you'll find in the larger area.

What are vacation rentals like in East Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in East Chatham. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.