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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Housatonic vacation homes

Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3)
"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 AED 496
AED 890 total
includes taxes & fees
15 Dec - 16 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is AED 479
AED 847 total
includes taxes & fees
15 Dec - 16 Dec
Home in Great Barrington
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 535
AED 1,373 total
includes taxes & fees
15 Dec - 16 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Property grounds
All the comforts of home

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (28)
"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
12 Dec - 13 Dec
All the comforts of home
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AED 588
AED 1,433 total
includes taxes & fees
15 Dec - 16 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is AED 496
AED 1,357 total
includes taxes & fees
12 Dec - 13 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 724
AED 1,633 total
includes taxes & fees
14 Dec - 15 Dec
Cheerful 3-bedroom cottage with woodstove
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
The price is AED 683
AED 1,984 total
includes taxes & fees
12 Dec - 13 Dec
Perfect House In Hillsdale, Brings Friends & Fam
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!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
Pittsfield
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 1,098
AED 1,936 total
includes taxes & fees
7 Jan - 8 January 2026
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington
Great Barrington
9.4 out of 10, Exceptional, (6)
The price is AED 744
AED 1,093 total
includes taxes & fees
15 Dec - 16 Dec
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is AED 1,047
AED 1,891 total
includes taxes & fees
14 Dec - 15 Dec
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
2.0 star property
Stottville
The price is AED 529
AED 1,115 total
includes taxes & fees
14 Dec - 15 Dec
Hudson Hot Tub & Pet Escape
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

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
The price is AED 970
AED 2,010 total
includes taxes & fees
14 Dec - 15 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Outdoor spa tub
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Valatie
10.0 out of 10, Exceptional, (58)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
The price is AED 992
AED 1,966 total
includes taxes & fees
14 Dec - 15 Dec
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Property grounds
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!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (2)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,079
AED 4,878 total
includes taxes & fees
12 Dec - 13 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is AED 1,183
AED 2,690 total
includes taxes & fees
12 Dec - 13 Dec
Comfortable Berkshires retreat on mtn resort, SISO
Interior
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is AED 825
AED 1,892 total
includes taxes & fees
19 Dec - 20 Dec
Artists’ Hideaway in Old Chatham
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,561
AED 2,900 total
includes taxes & fees
17 Dec - 18 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,163
AED 4,035 total
includes taxes & fees
15 Dec - 16 Dec
Hancock Village Inn Near Jiminy Peak
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 Housatonic Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. "
Meaghan 1-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel