Holiday Homes in Housatonic

  • 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

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 Housatonic holiday homes

Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
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 NZ$439
includes taxes & fees
8 Feb - 9 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Smart TV, books

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
9.8 out of 10, Exceptional, (11 reviews)
"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 NZ$636
includes taxes & fees
1 Feb - 2 Feb
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Property grounds

All the comforts of home

All the comforts of home
Hudson
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 NZ$233
includes taxes & fees
8 Feb - 9 Feb
All the comforts of home
Exterior

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 NZ$543
includes taxes & fees
4 Feb - 5 Feb
Near Tanglewood: Historic Summer Retreat
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
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 NZ$631
includes taxes & fees
2 Feb - 3 Feb
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
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 NZ$475
includes taxes & fees
2 Mar - 3 Mar
Home in Great Barrington
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
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 NZ$737
includes taxes & fees
1 Feb - 2 Feb
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, stovetop, dishwasher

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 NZ$915
includes taxes & fees
2 Feb - 3 Feb
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
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 NZ$486
includes taxes & fees
8 Feb - 9 Feb
Family Ski Getaway in the Berkshires
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is NZ$828
includes taxes & fees
2 Feb - 3 Feb
Artists’ Hideaway in Old Chatham
Interior

Suite 3 - Quiet and private accommodations in a country setting.

Suite 3 - Quiet and private accommodations in a country setting.
Spencertown
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
Suite 3 - Quiet and private accommodations in a country setting.
3 bedrooms, iron/ironing board, WiFi, bed sheets

Tranquil Victorian on Charming Street

Tranquil Victorian on Charming Street
Hudson
8.0 out of 10, Very good, (2 reviews)
"What a darling house! We stayed with my mother and my adult kids for Thanksgiving and it was the perfect spot! The host was most attentive to all of our questions and request ex! It’s the perfect location for visiting the Hudson Valley and the house was so comfortable and accommodating for all of us! We loved everything about it!"
United States
Mary R.
The price is NZ$926
includes taxes & fees
31 Jan - 1 Feb
Tranquil Victorian on Charming Street
Exterior

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, (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 NZ$1,048
includes taxes & fees
9 Feb - 10 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Fridge, microwave, oven, stovetop

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
The price is NZ$471
includes taxes & fees
1 Feb - 2 Feb
Hudson Hot Tub & Pet Escape
Outdoor dining

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 NZ$798
includes taxes & fees
31 Jan - 1 Feb
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
TV, fireplace, printers

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, (3 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 NZ$2,093
includes taxes & fees
31 Jan - 1 Feb
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
The price is NZ$498
includes taxes & fees
1 Feb - 2 Feb
Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is NZ$551
includes taxes & fees
23 Feb - 24 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
Smart TV, DVD player, books, stereo

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is NZ$838
includes taxes & fees
1 Mar - 2 Mar
Great Barrington Get Away
Interior

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 NZ$1,011
includes taxes & fees
2 Feb - 3 Feb
Luxury Barn Retreat — All-Season Escape Awaits!
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 Housatonic Hotel Reviews

Granville House

Granville House

10/10 Excellent
"This was a perfect getaway for our anniversary. Granville House is on our top 5 list of places stayed in the world! The property is cozy and every detail was thought out. After dinner in town, we enjoyed whisky from the bar, a board game by the fire and then borrowed a stack of vinyl from the extensive library to top off the night. Breakfast was delicious and we can not say enough about the hospitality shown to us. We will definitely be back on our next trip to the area!"
Tonya 1-night trip
Posted 2 days ago
Granville House

Find out more about Housatonic

Housatonic Holiday Homes information

Number of reviews
192
Accommodation
425 Holiday Homes
Lowest Price
NZ$233
Highest Price
NZ$2,093