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

East Chatham Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for East Chatham vacation rentals

A spacious room with a wooden ceiling, large windows, and a chandelier.

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.
$645 nightly
The price is $722
Sep 29 - Sep 30
Total with taxes and fees
Luxury Barn Retreat — All-Season Escape Awaits!
A modern building with a wooden deck and a door.

2. 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.
$511 nightly
The price is $572
Sep 28 - Sep 29
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,672 reviews)
"Love this place for a weekend getaway."
United States
Jacob
$122 nightly
The price is $136
Sep 27 - Sep 28
Total with taxes and fees
Vacation Village in the Berkshires
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, (178 reviews)
"Great little place."
United States
Kim
$118 nightly
The price is $132
Oct 5 - Oct 6
Total with taxes and fees
Micosta Leisure Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,153 reviews)
"Clean & comfortable stay"
United States
Robert
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

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.
$281 nightly
The price is $317
Sep 28 - Sep 29
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

7. 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)
"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.
$292 nightly
The price is $329
Oct 1 - Oct 2
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
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.
$293 nightly
The price is $328
Sep 27 - Sep 28
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

9. 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
$499 nightly
The price is $554
Sep 26 - Sep 27
Total with taxes and fees
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.

10. 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
$529 nightly
The price is $536
Sep 29 - Sep 30
Total with taxes and fees
NEW RENO Historic Creamery in Berkshires w/hot tub
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.
$463 nightly
The price is $470
Oct 5 - Oct 6
Total with taxes and fees
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A room with a sofa, a TV, a wooden floor, and a balcony with a view of trees.

12. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$2,031 nightly
The price is $2,059
Oct 13 - Oct 14
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

13. 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.
$205 nightly
The price is $208
Sep 27 - Sep 28
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

14. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
$284 nightly
The price is $317
Sep 27 - Sep 28
Total with taxes and fees
Riverside Retreat in the Berkshires
A bedroom with a bed, bedside lamp, and a window with curtains.

15. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
$630 nightly
The price is $691
Sep 29 - Sep 30
Total with taxes and fees
Ellie’s Overlook, best view in the Berkshires!
A rustic cabin interior with a stone fireplace, wooden beams, a bar area, and a cozy seating arrangement.

16. A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!
West Sand Lake
10.0 out of 10, Exceptional, (5 reviews)
"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"
United States
LisaL
$632 nightly
The price is $701
Sep 27 - Sep 28
Total with taxes and fees
A stunning, modern Lodge with rustic charm at June Farms!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

17. 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.
$505 nightly
The price is $561
Sep 26 - Sep 27
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A backyard with a fire pit, wooden deck, and string lights.

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

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
$324 nightly
The price is $363
Sep 27 - Sep 28
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A patio with stone flooring, wicker chairs, and a red umbrella. A lake with a dock and a small boat is visible in the background.

19. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Averill Park
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
United States
KenD
$643 nightly
The price is $713
Sep 27 - Sep 28
Total with taxes and fees
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
A wooden cabin with a porch, a door, and a window.

20. 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.
$165 nightly
The price is $183
Sep 26 - Sep 27
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"The hotel was nice & clean, the staff were very kind & helpful. Will be returning again & def recommend!"
Glen 1-night trip
Posted less than an hour ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about East Chatham

Everything you need to know about East Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the East Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect East Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

East Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in East Chatham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit East Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on East Chatham rentals

At Expedia, we put the best East Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top East Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream East Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around East Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Kinderhook 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.