Holiday Homes in East Chatham

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 July - 5 July
In three months
31 July - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for East Chatham holiday homes

Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (31 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is AU$199
includes taxes & fees
10 May - 11 May
All the comforts of home
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is AU$434
includes taxes & fees
12 May - 13 May
Cozy Riverside Berkshires Retreat
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is AU$472
includes taxes & fees
25 May - 26 May
Home in Great Barrington
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AU$671
includes taxes & fees
9 May - 10 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Terrace/patio

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is AU$660
includes taxes & fees
27 May - 28 May
Treat yourself at the stunning June Farms Wellness Huts!
Exterior detail

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is AU$725
includes taxes & fees
20 May - 21 May
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Dining

Hudson Hot Tub Escape | Pet-Friendly

Hudson Hot Tub Escape | Pet-Friendly
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$527
includes taxes & fees
10 May - 11 May
Hudson Hot Tub Escape | Pet-Friendly
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is AU$671
includes taxes & fees
1 June - 2 June
Charles Cottage Near Warren St New Renovation
Fridge, microwave, oven, stovetop

Perfect 4-bedroom house with AC in tranquil Albany

Perfect 4-bedroom house with AC in tranquil Albany
Delaware Avenue
The price is AU$751
includes taxes & fees
19 May - 20 May
Perfect 4-bedroom house with AC in tranquil Albany
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$683
includes taxes & fees
10 May - 11 May
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop

Modern and Cozy Pine Hills Home from Early 1900s

Modern and Cozy Pine Hills Home from Early 1900s
Pine Hills
10.0 out of 10, Exceptional, (57 reviews)
"We loved this place. It was very clean, hosts were very helpful and communicated quickly when we had questions. We both commented to each other that we would stay there again if we ever go to Albany again. "
United States
Lori N.
The price is AU$325
includes taxes & fees
12 May - 13 May
Modern and Cozy Pine Hills Home from Early 1900s
Interior

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (26 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is AU$1,036
includes taxes & fees
14 May - 15 May
Modern Victorian Walk to Main Street
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AU$991
includes taxes & fees
12 May - 13 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor dining

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is AU$387
includes taxes & fees
11 May - 12 May
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (9 reviews)
"Kind and responsive host."
United States
Javier
The price is AU$748
includes taxes & fees
12 May - 13 May
Comfortable Berkshires retreat on mtn resort, SISO
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$784
includes taxes & fees
11 May - 12 May
Treetop Hideaway in Tyringham
Smart TV, books

Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet

Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet
Hudson
The price is AU$623
includes taxes & fees
10 May - 11 May
Discover Hudson CharmHouse,where Hudson's sophistication and historic charm meet
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$774
includes taxes & fees
9 May - 10 May
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 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 AU$437
includes taxes & fees
11 May - 12 May
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Hillsdale
10.0 out of 10, Exceptional, (128 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Breakfast was ok. It was difficult to adjust room temp. Very inconvenient to take luggage to second floor for seniors. There should be a lif."
RAI AJIT 2-night trip
Posted 9 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about East Chatham

East Chatham Holiday Homes information

Number of reviews
395
Accommodation
474 Holiday Homes
Lowest Price
AU$199
Highest Price
AU$1,036