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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for East Chatham vacation rentals

Interior

1. 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 ￥51,721
￥96,142 total
includes taxes & fees
Sep 15 - Sep 16
Luxury Barn Retreat — All-Season Escape Awaits!
Dining

2. 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 ￥38,443
￥48,926 total
includes taxes & fees
Sep 17 - Sep 18
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

3. 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 ￥38,443
￥48,926 total
includes taxes & fees
Sep 13 - Sep 14
BLUSH: Boutique TINY home*private spa*walk to town
Lobby

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,139 reviews)
"Clean & comfortable stay"
United States
Robert
The price is ￥12,290
￥17,177 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
Coffee/tea maker, fridge, microwave, oven

5. 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)
"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 ￥10,732
￥30,516 total
includes taxes & fees
Sep 14 - Sep 15
NEW RENO - Chalet-style farm loft near Tanglewood
Exterior

6. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (173 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is ￥18,135
￥20,312 total
includes taxes & fees
Sep 16 - Sep 17
Micosta Leisure Inn
Property grounds

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, Exceptional, (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 ￥30,664
￥52,374 total
includes taxes & fees
Sep 21 - Sep 22
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Lobby

8. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,627 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is ￥14,587
￥17,977 total
includes taxes & fees
Sep 22 - Sep 23
Vacation Village in the Berkshires
Exterior

9. 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 ￥19,165
￥28,081 total
includes taxes & fees
Sep 12 - Sep 13
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

10. 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 ￥50,794
￥108,073 total
includes taxes & fees
Sep 15 - Sep 16
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Property grounds

11. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (59 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,041
￥20,278 total
includes taxes & fees
Sep 14 - Sep 15
All comforts of home
Beach

12. 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 ￥16,983
￥36,540 total
includes taxes & fees
Sep 13 - Sep 14
Berkshires Apartment at the Stephentown Hotel
Property grounds

13. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (36 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,283
￥21,672 total
includes taxes & fees
Sep 14 - Sep 15
All the comforts of home
Exterior

14. 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 ￥34,583
￥76,688 total
includes taxes & fees
Sep 13 - Sep 14
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Outdoor dining

15. 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, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is ￥37,103
￥78,046 total
includes taxes & fees
Sep 14 - Sep 15
NEW RENO Historic Creamery in Berkshires w/hot tub
Property grounds

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, 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 ￥17,172
￥37,505 total
includes taxes & fees
Sep 14 - Sep 15
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Terrace/patio

17. 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 ￥28,671
￥56,152 total
includes taxes & fees
Sep 16 - Sep 17
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Coffee/tea maker, fridge, microwave, stovetop

18. 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 ￥27,173
￥87,229 total
includes taxes & fees
Sep 13 - Sep 14
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Coffee/tea maker, fridge, microwave, oven

19. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is ￥17,369
￥25,437 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 1-bedroom studio in serene Great Barrington with AC
Gift shop

20. 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 ￥15,563
￥35,492 total
includes taxes & fees
Sep 14 - Sep 15
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Beautiful location and views. Spacious room with all amenities."
Sherry 1-night trip
Posted 17 hours ago
Vacation Village in the Berkshires

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:

  • View our selection of featured holiday rentals in East Chatham
  • Use the map to find apartments and other holiday homes in the East Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in East Chatham while they last

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 7 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 Queechy Lake 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.