Search Vacation Homes in Chatham

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Vacation Homes in Chatham

Fridge, microwave, oven, stovetop
Home in Great Barrington
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Crisp and clean with a great location.Wonderful choice."
United States
Richard B.
The price is AED 698
AED 1,120 total
includes taxes & fees
23 Nov - 24 Nov
Home in Great Barrington
Property grounds
All the comforts of home
All the comforts of home
9.2 out of 10, Wonderful, (26)
"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 AED 390
AED 519 total
includes taxes & fees
27 Oct - 28 Oct
All the comforts of home
Outdoor spa tub
Tiny Home w/ Hot Tub and Sunset View!
Tiny Home w/ Hot Tub and Sunset View!
10.0 out of 10, Exceptional, (1)
"Very private and quiet, we had a wonderful time! Stars were very bright at night and we even heard coyotes in the distance! "
United States
Blake
The price is AED 235
AED 373 total
includes taxes & fees
27 Oct - 28 Oct
Tiny Home w/ Hot Tub and Sunset View!
Property grounds
Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 724
AED 1,658 total
includes taxes & fees
11 Nov - 12 Nov
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
The price is AED 628
AED 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Near Tanglewood: Historic Summer Retreat
Exterior
Modern Luxurious Cabin, Catskills - The Tiny Nook
Modern Luxurious Cabin, Catskills - The Tiny Nook
10.0 out of 10, Exceptional, (5)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is AED 588
AED 1,254 total
includes taxes & fees
28 Oct - 29 Oct
Modern Luxurious Cabin, Catskills - The Tiny Nook
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape
Hudson Hot Tub & Pet Escape
2.0 star property
The price is AED 401
AED 992 total
includes taxes & fees
4 Nov - 5 Nov
Hudson Hot Tub & Pet Escape
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"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 AED 698
AED 1,719 total
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AED 591
AED 1,792 total
includes taxes & fees
26 Oct - 27 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Fridge, microwave, oven, stovetop
Great Barrington Get Away
Great Barrington Get Away
9.4 out of 10, Exceptional, (24)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
United States
Amy B.
The price is AED 937
AED 1,764 total
includes taxes & fees
27 Oct - 28 Oct
Great Barrington Get Away
Interior
Spacious Victorian in the heart of Catskill Village - Close to All
Spacious Victorian in the heart of Catskill Village - Close to All
9.8 out of 10, Exceptional, (7)
"We so enjoyed our stay at the house! It was so clean and spacious. The decorating is lovely as are the historic details of the house. It was very comfortable on very hot days and the pool was a delight. The host was very responsive when we had questions. We would welcome the opportunity to stay again!"
United States
Patricia J.
The price is AED 1,215
AED 1,927 total
includes taxes & fees
26 Oct - 27 Oct
Spacious Victorian in the heart of Catskill Village - Close to All
Terrace/patio
Treat yourself at the stunning June Farms Wellness Huts!
Treat yourself at the stunning June Farms Wellness Huts!
10.0 out of 10, Exceptional, (8)
"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 AED 972
AED 1,711 total
includes taxes & fees
5 Nov - 6 Nov
Treat yourself at the stunning June Farms Wellness Huts!
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is AED 1,102
AED 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Bungalow in the Berkshires
Game room
Pet Friendly Riverfront Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 950 total
includes taxes & fees
29 Oct - 30 Oct
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
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!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AED 988
AED 1,806 total
includes taxes & fees
26 Oct - 27 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor spa tub
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
10.0 out of 10, Exceptional, (54)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
The price is AED 992
AED 1,975 total
includes taxes & fees
26 Oct - 27 Oct
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Smart TV, books
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
10.0 out of 10, Exceptional, (1)
"Perfect Hudson Valley Girls weekend! The house was gorgeous, so incredibly clean, comfortable beds, beautiful outdoor fire pit area with jacuzzi overlooking the river. All the little efforts were put into the property to make it feel like an intimate home, like providing plenty of additional towels for the jacuzzi, shampoo / conditioner in the showers and more. We were able to spend each day in Hudson downtown enjoying all the boutiques and restaurants because it was such an easy drive into...
United States
Caitlin W.
The price is AED 1,076
AED 2,246 total
includes taxes & fees
26 Oct - 27 Oct
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Smart TV, fireplace, books
Cozy. Clean. Free bagel shop.
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
United States
Carly F.
The price is AED 1,322
AED 2,232 total
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
The price is AED 988
AED 2,051 total
includes taxes & fees
26 Oct - 27 Oct
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Property grounds
The Lakeshore House
The Lakeshore House
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is AED 1,781
AED 2,945 total
includes taxes & fees
25 Oct - 26 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge