Holiday Homes in Chatham

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Chatham holiday homes

Property grounds

Holiday Home in Chatham

Renovated house. Built in 1890s. No neighbors in sight.
The price is AU$441
includes taxes & fees
28 Jan - 29 Jan
Renovated house. Built in 1890s. No neighbors in sight.
Exterior

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
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 AU$481
includes taxes & fees
28 Jan - 29 Jan
Near Tanglewood: Historic Summer Retreat
Smart TV, books

Holiday Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 AU$645
includes taxes & fees
28 Jan - 29 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 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 AU$413
includes taxes & fees
23 Feb - 24 Feb
Home in Great Barrington
TV, offices

Holiday Home in Catskill

Catskill Stay w/ Deck & Fire Pit
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 AU$700
includes taxes & fees
28 Jan - 29 Jan
Catskill Stay w/ Deck & Fire Pit
Interior

Holiday Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
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 AU$385
includes taxes & fees
1 Feb - 2 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

Holiday Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29 reviews)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is AU$207
includes taxes & fees
28 Jan - 29 Jan
All the comforts of home
Interior

Holiday Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is AU$534
includes taxes & fees
10 Feb - 11 Feb
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, stovetop, dishwasher

Holiday Home in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$800
includes taxes & fees
5 Feb - 6 Feb
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

Holiday Home in Catskill

Modern Luxurious Cabin, Catskills - The Tiny Nook
10.0 out of 10, Exceptional, (8 reviews)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is AU$487
includes taxes & fees
4 Feb - 5 Feb
Modern Luxurious Cabin, Catskills - The Tiny Nook
Fridge, microwave, oven, stovetop

Holiday Home in Stottville

Hudson Hot Tub & Pet Escape
The price is AU$415
includes taxes & fees
28 Jan - 29 Jan
Hudson Hot Tub & Pet Escape
Interior

Holiday Home in Spencertown

Suite 3 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is AU$393
includes taxes & fees
28 Jan - 29 Jan
Suite 3 - Quiet and private accommodations in a country setting.
Interior

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.4 out of 10, Exceptional, (8 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$432
includes taxes & fees
2 Feb - 3 Feb
Family Ski Getaway in the Berkshires
Terrace/patio

Holiday Home in West Sand Lake

Treat yourself at the stunning June Farms Wellness Huts!
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$648
includes taxes & fees
9 Feb - 10 Feb
Treat yourself at the stunning June Farms Wellness Huts!
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Holiday Home in Albany

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
8.0 out of 10, Very good, (1 review)
"Overall nice stay "
United States
Anonymous traveller
The price is AU$449
includes taxes & fees
5 Feb - 6 Feb
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
Outdoor dining

Holiday Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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$699
includes taxes & fees
29 Jan - 30 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
TV, fireplace

Holiday Home in Old Chatham

Artists’ Hideaway in Old Chatham
The price is AU$737
includes taxes & fees
28 Jan - 29 Jan
Artists’ Hideaway in Old Chatham
Beach nearby

Holiday Home in Catskill

1 Bedroom | Cozy Lounge | Spacious
1 Bedroom | Cozy Lounge | Spacious
Exterior detail

Holiday Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is AU$492
includes taxes & fees
26 Feb - 27 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
Exterior

Holiday Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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 AU$916
includes taxes & fees
9 Feb - 10 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Everything was great, the staff, the room, and the amenities. We will be coming back. "
David 1-night trip
Posted 2 days ago
Vacation Village in the Berkshires

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
159
Accommodation
490 Holiday Homes
Lowest Price
AU$207
Highest Price
AU$928