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

Housatonic Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Housatonic vacation rentals

Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is ￥26,882
￥48,902 total
includes taxes & fees
Sep 25 - Sep 26
Sweet Cozy Victorian in Housatonic. Close to everything.
Lobby

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,143 reviews)
"Clean & comfortable stay"
United States
Robert
The price is ￥12,227
￥17,090 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
Coffee/tea maker, fridge, microwave, oven

3. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is ￥17,281
￥25,309 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 1-bedroom studio in serene Great Barrington with AC
Interior

4. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (25 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 ￥31,106
￥48,301 total
includes taxes & fees
Sep 21 - Sep 22
Riverside Retreat in the Berkshires
Coffee/tea maker, fridge, microwave, oven

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥29,309
￥47,324 total
includes taxes & fees
Sep 15 - Sep 16
Home in Great Barrington
Beach nearby, sun loungers, beach towels

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is ￥33,641
￥53,533 total
includes taxes & fees
Sep 14 - Sep 15
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Exterior

7. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (174 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is ￥18,043
￥20,209 total
includes taxes & fees
Sep 16 - Sep 17
Micosta Leisure Inn
Coffee/tea maker, fridge, microwave, oven

8. 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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is ￥10,753
￥30,575 total
includes taxes & fees
Sep 14 - Sep 15
NEW RENO - Chalet-style farm loft near Tanglewood
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥48,157
￥84,848 total
includes taxes & fees
Sep 14 - Sep 15
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Terrace/patio

10. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is ￥30,722
￥56,430 total
includes taxes & fees
Sep 14 - Sep 15
Ideal location for summer and winter activities with plenty of outdoor space.
Smart TV, fireplace

11. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very Good, (1 review)
"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 ￥7,988
￥44,612 total
includes taxes & fees
Sep 16 - Sep 17
Real Estate: Therapy - Lake, Laundry, Love it
TV, fireplace, printers

13. 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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is ￥86,959
￥204,030 total
includes taxes & fees
Sep 14 - Sep 15
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

14. 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, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is ￥81,413
￥138,639 total
includes taxes & fees
Sep 20 - Sep 21
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

15. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (59 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,069
￥20,316 total
includes taxes & fees
Sep 14 - Sep 15
All comforts of home
TV, DVD player, books, video library

16. 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 ￥16,590
￥38,476 total
includes taxes & fees
Sep 28 - Sep 29
1800s Carriage house in Berkshires / Hudson Valley
TV

17. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥43,318
￥88,651 total
includes taxes & fees
Sep 21 - Sep 22
Treetop Hideaway in Tyringham
Interior

18. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,396
￥57,617 total
includes taxes & fees
Sep 15 - Sep 16
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Property grounds

19. 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, (13 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 ￥30,722
￥52,473 total
includes taxes & fees
Sep 20 - Sep 21
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Property grounds

20. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (36 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,313
￥21,712 total
includes taxes & fees
Sep 14 - Sep 15
All the comforts of home
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

Little Cat Lodge

Little Cat Lodge

10/10 Excellent
"Little Cat Lodge was an excellent stay. Visited in mid-September so was able to use the heated pool. The food menu at Little Cat is very tasty, good quality and Staff is very friendly. Breakfast was okay, but approx 10-15 minutes to town that has plenty of additional food options, Clean rooms, nice grounds and cool lodge area. The views are of a Ski mountain which is very nice and tranquil."
Shaun 2-night trip
Posted 1 hour ago
Little Cat Lodge

Find out more about Housatonic

Search for holiday rentals in Housatonic on Expedia! You can easily find your home rentals, villas, holiday apartments in Housatonic using one of the methods below:

  • View our selection of featured holiday rentals in Housatonic
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Look no further and take a look at our great range of rental properties in Housatonic!

Frequently asked questions

Can I find vacation rentals in Housatonic?

Yes, there are vacation rentals near the most popular local attractions in Housatonic, or you can choose a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Housatonic?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: You might want to consider this vacation home rental near Housatonic, which is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Housatonic?

Expedia has 11 vacation rentals for your stay in Housatonic.

What’s there to see and do in Housatonic?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Housatonic River. Norman Rockwell Museum and Berkshire Botanical Garden are a couple of places you'll find in the larger area.

What’s a vacation rental in Housatonic like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Housatonic. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips.