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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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 AED 643
AED 1,173 total
includes taxes & fees
9 Sep - 10 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

2. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 744
AED 1,163 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Riverside Berkshires Retreat
Exterior

3. 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 AED 1,690
AED 3,143 total
includes taxes & fees
28 Sep - 29 Sep
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV, fireplace, printers

4. 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 AED 2,079
AED 4,854 total
includes taxes & fees
6 Sep - 7 Sep
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Lobby

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,115 reviews)
"Clean & comfortable stay"
United States
Robert
The price is AED 292
AED 409 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Lobby

6. Modern Designer Chalet on 5.5 Private Acres Near Tanglewood

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
West Stockbridge
10.0 out of 10, Exceptional, (6 reviews)
"The home was great! It was tucked away but still very close to everything! Our family enjoyed our stay and Michelle was very welcoming and had everything at the house for us to feel comfortable."
United States
Jon U.
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
3 bedrooms, iron/ironing board, WiFi, bed sheets

7. 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 AED 1,165
AED 2,036 total
includes taxes & fees
14 Sep - 15 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Coffee/tea maker, fridge, microwave, oven

8. 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 AED 876
AED 1,352 total
includes taxes & fees
7 Sep - 8 Sep
Home in Great Barrington
Beach nearby, sun loungers, beach towels

9. 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, (3 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 AED 863
AED 1,325 total
includes taxes & fees
14 Sep - 15 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
4 bedrooms, travel crib, WiFi, bed sheets

10. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
Stylish Mid-century Modern Berkshires Cape
Coffee/tea maker, fridge, microwave, oven

11. 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)
"Michael’s place in Great Barrington MA was incredible. It was clean, very well appointed, affordable and so quiet. It is also very close to numerous restaurant options and grocery stores. I thought the place was very cozy and so comfortable. This was a stopping off point for me so I unfortunately was not able to stay longer. Next time I am Great Barrington I will definitely look up Michael’s place. Thank you Michael."
United States
Paul J.
The price is AED 413
AED 605 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 1-bedroom studio in serene Great Barrington with AC
Exterior

12. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (171 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is AED 436
AED 489 total
includes taxes & fees
7 Sep - 8 Sep
Micosta Leisure Inn
Smart TV, books

13. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AED 1,483
AED 2,484 total
includes taxes & fees
6 Sep - 7 Sep
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Terrace/patio

14. 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 AED 735
AED 1,411 total
includes taxes & fees
7 Sep - 8 Sep
Ideal location for summer and winter activities with plenty of outdoor space.
Smart TV

15. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.6 out of 10, Exceptional, (7 reviews)
stylish Berkshires Retreat
TV

16. 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 AED 1,036
AED 2,139 total
includes taxes & fees
21 Sep - 22 Sep
Treetop Hideaway in Tyringham
Terrace/patio

17. Secluded Cabin in the Woods, where the Berkshires meet the Hudson Valley.

Secluded Cabin in the Woods, where the Berkshires meet the Hudson Valley.
Canaan
Secluded Cabin in the Woods, where the Berkshires meet the Hudson Valley.
Exterior detail

18. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Property grounds

19. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 907
AED 1,908 total
includes taxes & fees
22 Sep - 23 Sep
Cheerful 3-bedroom cottage with woodstove
Desk, iron/ironing board, WiFi, bed sheets

20. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is AED 551
AED 708 total
includes taxes & fees
7 Sep - 8 Sep
The Brooks Motel: Exceptional Suite
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."
Janet L. 2-night trip
Posted 9 hours ago
Quality Inn Great Barrington

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: Visitors like this Housatonic vacation home rental. It 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 12 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.