Search Vacation Homes in Housatonic

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Housatonic vacation homes

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ¥25,360
¥62,807 total
includes taxes & fees
Apr 6 - Apr 7
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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 ¥16,811
¥22,375 total
includes taxes & fees
Mar 27 - Mar 28
All the comforts of home

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 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 ¥29,206
¥47,477 total
includes taxes & fees
Mar 30 - Mar 31
Home in Great Barrington

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥23,080
¥58,669 total
includes taxes & fees
Apr 6 - Apr 7
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥32,056
¥50,129 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Riverside Berkshires Retreat

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 ¥20,516
¥57,726 total
includes taxes & fees
Mar 31 - Apr 1
Near Tanglewood: Historic Summer Retreat

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 ¥23,935
¥61,735 total
includes taxes & fees
Mar 30 - Mar 31
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 ¥42,599
¥76,228 total
includes taxes & fees
Mar 26 - Mar 27
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is ¥25,537
¥80,902 total
includes taxes & fees
Mar 26 - Mar 27
Artists’ Hideaway in Old Chatham

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, (35 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 ¥56,830
¥114,934 total
includes taxes & fees
Mar 27 - Mar 28
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 ¥37,517
¥79,924 total
includes taxes & fees
Mar 30 - Mar 31
Cheerful 3-bedroom cottage with woodstove

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, (4 reviews)
"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 ¥89,614
¥210,259 total
includes taxes & fees
Mar 26 - Mar 27
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 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 ¥41,894
¥88,900 total
includes taxes & fees
Mar 30 - Mar 31
Treetop Hideaway in Tyringham

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is ¥53,161
¥99,175 total
includes taxes & fees
Mar 30 - Mar 31
Luxury Barn Retreat — All-Season Escape Awaits!

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ¥59,363
¥116,172 total
includes taxes & fees
Apr 1 - Apr 2
Spacious 5-bedroom house in charming Lee with WiFi

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (5 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is ¥28,494
¥72,144 total
includes taxes & fees
Mar 30 - Mar 31
Sun Filled Lenox Retreat - Minutes to Tanglewood!

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
The price is ¥16,463
¥52,302 total
includes taxes & fees
Mar 26 - Mar 27
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

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 ¥27,703
¥87,597 total
includes taxes & fees
Mar 26 - Mar 27
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥24,077
¥46,290 total
includes taxes & fees
Mar 30 - Mar 31
Hudson Hot Tub & Pet Escape
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Housatonic Hotel Reviews

Find out more about Housatonic

Housatonic Vacation Homes information

Number of reviews
239
Accommodation
425 Vacation Homes
Lowest Price
¥22,375
Highest Price
¥210,259