Housatonic Vacation Rentals from ￥17,152: Search Short-Term Rentals

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Our top choices for Housatonic vacation rentals

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.

Housatonic

Peter S.

￥49,245 total

includes taxes & fees

Sep 9 - Sep 10

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Pittsfield

Robert

￥17,152 total

includes taxes & fees

Oct 1 - Oct 2

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

Shelly B.

￥25,398 total

includes taxes & fees

Sep 15 - Sep 16

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

4. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

￥48,814 total

includes taxes & fees

Sep 9 - Sep 10

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Great Barrington

HEATHER G.

￥47,491 total

includes taxes & fees

Sep 15 - Sep 16

A sandy beach with a lake and forest in the background.

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

Great Barrington

Kristin O.

￥54,237 total

includes taxes & fees

Sep 14 - Sep 15

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

7. Micosta Leisure Inn

Hudson

Andrea

￥20,510 total

includes taxes & fees

Sep 10 - Sep 11

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Great Barrington

Mary R.

￥85,963 total

includes taxes & fees

Sep 14 - Sep 15

A wooden cabin with a porch, a grill, and a flower planter.

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

Hillsdale

Kenny

￥58,528 total

includes taxes & fees

Sep 9 - Sep 10

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.

10. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Rebecca K.

￥204,746 total

includes taxes & fees

Sep 9 - Sep 10

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveler

￥131,894 total

includes taxes & fees

Sep 28 - Sep 29

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

New Lebanon

Varun M.

￥32,064 total

includes taxes & fees

Sep 10 - Sep 11

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

13. Treetop Hideaway in Tyringham

Monterey

"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!! "

Samantha G.

￥88,963 total

includes taxes & fees

Sep 21 - Sep 22

A spacious living room with a dining area, a kitchen, and a large window.

14. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

￥34,548 total

includes taxes & fees

Sep 9 - Sep 10

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

￥45,974 total

includes taxes & fees

Sep 13 - Sep 14

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

￥64,054 total

includes taxes & fees

Sep 29 - Sep 30

A camping setup with a metal chair and a table by a river in a forest.

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

Chatham

Jen R.

￥52,658 total

includes taxes & fees

Sep 20 - Sep 21

A spacious living area with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

18. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

￥49,746 total

includes taxes & fees

Sep 9 - Sep 10

A wooden deck with a staircase leading to a covered porch area.

19. All comforts of home

Hudson

Georgine

￥20,388 total

includes taxes & fees

Sep 10 - Sep 11

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.

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

Sherwood Forest

Sharon K.

￥57,820 total

includes taxes & fees

Sep 10 - Sep 11

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Top Housatonic Hotel Reviews

FairBridge Inn Express

10/10 Excellent

"Good clean cheap hotel"

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

The Red Lion Inn

8/10 Good

"The Inn is very welcoming with a broad front porch filled with wicker chairs and rockers. Inside there are many sitting rooms, a restaurant and tavern, gift and floral shops and access to an outdoor pool. Well loved antiques are everywhere for comfortable seating throughout the property. Rooms facing the streets can be noisy with traffic. Lots of atmosphere, history and great location for shopping, sightseeing and dining."

Find out more about Housatonic

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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.

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Check prices for these dates

Our top choices for Housatonic vacation rentals

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

2. Berkshire Mountain Lodge

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

4. Riverside Retreat in the Berkshires

5. Home in Great Barrington

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

7. Micosta Leisure Inn

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

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

10. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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

13. Treetop Hideaway in Tyringham

14. 1800s Carriage house in Berkshires / Hudson Valley

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

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

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

18. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

19. All comforts of home

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

Find vacation rentals that suit your style

Top Housatonic Hotel Reviews

FairBridge Inn Express

Jiminy Peak Mountain Resort

Quality Inn Lee - Lenox South

The Whitlock

Little Cat Lodge

The Red Lion Inn

Berkshire Mountain Lodge

Hotel On North

Berkshires Untold

Find out more about Housatonic

Frequently asked questions

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