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

East Chatham Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for East Chatham holiday 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.
The price is AU$1,048
includes taxes & fees
5 Oct - 6 Oct
Luxury Barn Retreat — All-Season Escape Awaits!
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

2. 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 AU$457
includes taxes & fees
6 Oct - 7 Oct
Sugar Shack - 300 square feet of pure sweetness.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

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 AU$482
includes taxes & fees
2 Nov - 3 Nov
BLUSH: Boutique TINY home*private spa*walk to town
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,173 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is AU$170
includes taxes & fees
18 Oct - 19 Oct
Berkshire Mountain Lodge
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. 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 AU$161
includes taxes & fees
27 Oct - 28 Oct
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.

6. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,704 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is AU$154
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

7. 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 AU$297
includes taxes & fees
5 Oct - 6 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A modern building with a wooden deck and a door.

8. 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 AU$811
includes taxes & fees
5 Oct - 6 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A camping setup with a metal chair and a table by a river in a forest.

9. 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 AU$487
includes taxes & fees
5 Oct - 6 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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 AU$332
includes taxes & fees
18 Oct - 19 Oct
Berkshires Apartment at the Stephentown Hotel
A wooden deck with a staircase leading to a covered porch area.

11. 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 AU$193
includes taxes & fees
7 Oct - 8 Oct
All comforts of home
A wooden cabin with a porch, a door, and a window.

12. 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 AU$266
includes taxes & fees
5 Oct - 6 Oct
Taborton Harvest Boulder Pines Cabin in the woods
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, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AU$206
includes taxes & fees
5 Oct - 6 Oct
All the comforts of home
A white two-story house with a porch, surrounded by trees and a hill.

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 AU$664
includes taxes & fees
5 Oct - 6 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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 AU$809
includes taxes & fees
13 Oct - 14 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

16. 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 AU$797
includes taxes & fees
5 Oct - 6 Oct
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.

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, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is AU$818
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is AU$204
includes taxes & fees
11 Oct - 12 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A living room with a brown sofa, a glass coffee table, a dark wooden dresser, and a green plant.

19. 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 AU$255
includes taxes & fees
5 Oct - 6 Oct
Chic Madison Parkview
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

20. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is AU$377
includes taxes & fees
18 Oct - 19 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

8/10 Good
"Although WAZE got us to the property we weren't sure we arrived at the right place. There is was no signage indicating we were at the Hampton Inn. Also, the valets are not at the front, they are in the back lot."
Joe 1-night trip
Posted less than an hour ago
Hampton Inn & Suites Albany-Downtown

Find out more about East Chatham

Everything you need to know about East Chatham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the East Chatham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

East Chatham holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A East Chatham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of East Chatham holiday rentals we have selected for you start as low as AU$154 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on East Chatham rentals

At Expedia, we put the best East Chatham holiday 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 holiday.

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 holiday rental in East Chatham?

Yes, there are holiday rentals close to the most popular sights in East Chatham, or you can select a more secluded option if you're looking for a relaxing stay.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of East Chatham is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in East Chatham?

Expedia has 7 holiday 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 wider area.

What are holiday rentals like in East Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in East Chatham. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family trip.