Holiday Homes in East Chatham

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for East Chatham holiday homes

Living area

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is NZ$878
includes taxes & fees
5 May - 6 May
Charles Cottage Near Warren St New Renovation
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 NZ$240
includes taxes & fees
5 May - 6 May
All the comforts of home
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (30 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is NZ$537
includes taxes & fees
4 May - 5 May
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$533
includes taxes & fees
3 May - 4 May
Cozy Riverside Berkshires Retreat
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 NZ$812
includes taxes & fees
18 May - 19 May
Treat yourself at the stunning June Farms Wellness Huts!
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 NZ$826
includes taxes & fees
1 May - 2 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$534
includes taxes & fees
20 May - 21 May
Hudson Hot Tub & Pet Escape
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Kind and responsive host."
United States
Javier
The price is NZ$903
includes taxes & fees
1 May - 2 May
Comfortable Berkshires retreat on mtn resort, SISO
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 NZ$481
includes taxes & fees
4 May - 5 May
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is NZ$703
includes taxes & fees
4 May - 5 May
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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, (6 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is NZ$804
includes taxes & fees
5 May - 6 May
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
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 NZ$475
includes taxes & fees
4 May - 5 May
Modern and Cozy Pine Hills Home from Early 1900s
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 NZ$846
includes taxes & fees
20 May - 21 May
Cheerful 3-bedroom cottage with woodstove
Interior

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is NZ$867
includes taxes & fees
26 May - 27 May
Artists’ Hideaway in Old Chatham
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, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is NZ$1,207
includes taxes & fees
4 May - 5 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

Downtown 3BR duplex full kitchen parking off i-787

Downtown 3BR duplex full kitchen parking off i-787
Arbor Hill
10.0 out of 10, Exceptional, (5 reviews)
"The owners gave us fresh baked bread - twice. Also helped us get parking in a location with very few spots. Real nice owners for this property and would come back any time! "
United States
Victor
The price is NZ$491
includes taxes & fees
4 May - 5 May
Downtown 3BR duplex full kitchen parking off i-787
Fridge, microwave, oven, stovetop

Modern House Near Hudson with Fire Pit and Privacy

Modern House Near Hudson with Fire Pit and Privacy
Hudson
The price is NZ$1,354
includes taxes & fees
3 May - 4 May
Modern House Near Hudson with Fire Pit and Privacy
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 NZ$1,281
includes taxes & fees
11 May - 12 May
Modern Victorian Walk to Main Street
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (6 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is NZ$448
includes taxes & fees
3 May - 4 May
Sweet Cozy Victorian in Housatonic. Close to everything.
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 NZ$938
includes taxes & fees
4 May - 5 May
Treetop Hideaway in Tyringham
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

Berkshires Untold

Berkshires Untold

8/10 Good
"All was good. Wished there was coffee in the room and the heating / cooling system had an off switch. For one night and the price, it was fine. Cool bar & outside area."
Susan 1-night trip
Posted 5 hours ago
Berkshires Untold

Find out more about East Chatham

East Chatham Holiday Homes information

Number of reviews
295
Accommodation
510 Holiday Homes
Lowest Price
NZ$240
Highest Price
NZ$1,354