A river flanked by autumn-colored trees and residential areas.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Housatonic vacation homes

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

1. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ￥31,374
￥55,021 total
includes taxes & fees
Oct 27 - Oct 28
Sweet Cozy Victorian in Housatonic. Close to everything.
A dining area with a wooden table and chairs, a ceiling fan, and a view of the outdoors through windows.

2. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥27,531
￥44,244 total
includes taxes & fees
Oct 26 - Oct 27
Leaf-Peeper Paradise in the Berkshires
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

3. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is ￥53,791
￥100,912 total
includes taxes & fees
Nov 1 - Nov 2
Secluded Family Home in Serene Stockbridge Woods
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥36,143
￥56,141 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

5. 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, (9 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 ￥88,804
￥208,359 total
includes taxes & fees
Oct 30 - Oct 31
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

6. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is ￥62,748
￥110,215 total
includes taxes & fees
Nov 16 - Nov 17
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern living room with a sofa, armchair, coffee table, and TV.

7. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is ￥45,884
￥94,183 total
includes taxes & fees
Nov 1 - Nov 2
Spacious Central Berkshires Home for Groups
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

8. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,414
￥108,416 total
includes taxes & fees
Nov 2 - Nov 3
Ellie’s Overlook, best view in the Berkshires!
A living room with a sofa, armchairs, a coffee table, and a television.

9. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is ￥49,838
￥99,650 total
includes taxes & fees
Oct 26 - Oct 27
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

10. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 ￥42,041
￥88,046 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Hideaway in Tyringham
A cozy living room with a sofa, a fireplace, and large windows.

11. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is ￥60,003
￥106,559 total
includes taxes & fees
Oct 27 - Oct 28
Luxury Barn Near Hudson With New Private Sauna
A camping setup with a metal chair and a table by a river in a forest.

12. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is ￥31,374
￥53,938 total
includes taxes & fees
Oct 26 - Oct 27
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

13. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is ￥10,981
￥32,629 total
includes taxes & fees
Oct 27 - Oct 28
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

14. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is ￥13,334
￥35,333 total
includes taxes & fees
Nov 5 - Nov 6
1800s Carriage house in Berkshires / Hudson Valley
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

15. 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, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,872
￥59,016 total
includes taxes & fees
Oct 26 - Oct 27
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

16. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥27,813
￥66,990 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful 3-bedroom cottage with woodstove
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

17. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥9,255
￥46,960 total
includes taxes & fees
Oct 28 - Oct 29
Real Estate: Therapy - Lake, Laundry, Love it
A wooden deck with a staircase leading to a covered porch area.

18. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is ￥16,660
￥22,174 total
includes taxes & fees
Nov 1 - Nov 2
All the comforts of home
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,131
￥61,713 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Beautiful setting. Spacious room. Even the machine-dispensed coffee was good. Five stars."
Anonymous traveler 1-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Housatonic

Housatonic Vacation Homes information

Number of reviews
244
Accommodation
409 Vacation Homes
Lowest Price
￥22,174
Highest Price
￥208,359