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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chatham holiday homes

Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
The price is £232
includes taxes & fees
8 Feb - 9 Feb
Renovated house. Built in 1890s. No neighbors in sight.
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is £201
includes taxes & fees
26 Feb - 27 Feb
Home in Great Barrington
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 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 £200
includes taxes & fees
8 Feb - 9 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is £245
includes taxes & fees
10 Feb - 11 Feb
Near Tanglewood: Historic Summer Retreat
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (9 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is £211
includes taxes & fees
26 Feb - 27 Feb
Family Ski Getaway in the Berkshires
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is £107
includes taxes & fees
16 Feb - 17 Feb
All the comforts of home
Fridge, microwave, oven, stovetop

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
The price is £226
includes taxes & fees
18 Feb - 19 Feb
Hudson Hot Tub & Pet Escape
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
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is £403
includes taxes & fees
8 Feb - 9 Feb
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is £332
includes taxes & fees
8 Feb - 9 Feb
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 £286
includes taxes & fees
10 Feb - 11 Feb
Historic Berkshires Home Near Tanglewood, Trails & Wineries
TV, offices

Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
8.8 out of 10, Excellent, (3 reviews)
"we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. "
United States
raquel p.
The price is £299
includes taxes & fees
10 Feb - 11 Feb
Catskill Stay w/ Deck & Fire Pit
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)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
The price is £370
includes taxes & fees
22 Feb - 23 Feb
Treat yourself at the stunning June Farms Wellness Huts!
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (8 reviews)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is £254
includes taxes & fees
23 Feb - 24 Feb
Modern Luxurious Cabin, Catskills - The Tiny Nook
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
Albany
8.0 out of 10, Very good, (1 review)
"Overall nice stay "
United States
Anonymous traveller
The price is £233
includes taxes & fees
9 Feb - 10 Feb
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is £379
includes taxes & fees
8 Feb - 9 Feb
Artists’ Hideaway in Old Chatham
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 £360
includes taxes & fees
16 Feb - 17 Feb
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is £472
includes taxes & fees
9 Feb - 10 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is £235
includes taxes & fees
26 Feb - 27 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
Smart TV, DVD player, books, stereo

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is £383
includes taxes & fees
1 Mar - 2 Mar
Great Barrington Get Away
Property grounds

The Lakeshore House

The Lakeshore House
Niverville
10.0 out of 10, Exceptional, (1 review)
"Excellent stay!"
United States
KEITARO A.
The price is £589
includes taxes & fees
8 Feb - 9 Feb
The Lakeshore House
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 Chatham Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Room was reasonably comfortable and always nice to be looking out at the mountain. Staff is always pleasant and efficient. Very good value for the money."
Nathaniel 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
188
Accommodation
490 Holiday Homes
Lowest Price
£107
Highest Price
£589