Housatonic Vacation Rentals

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Our top choices for Housatonic vacation rentals

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 CA $183
CA $363 total
includes taxes & fees
Feb 24 - Feb 25
Sweet Cozy Victorian in Housatonic. Close to everything.

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is CA $256
CA $286 total
includes taxes & fees
Mar 11 - Mar 12
Jiminy Peak Mountain Resort

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)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is CA $217
CA $532 total
includes taxes & fees
Feb 24 - Feb 25
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"The condo was in good shape with a great location for skiing. Howard was very responsive. "
United States
John M.
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is CA $266
CA $750 total
includes taxes & fees
Feb 22 - Feb 23
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is CA $160
CA $323 total
includes taxes & fees
Feb 22 - Feb 23
Berkshires Apartment at the Stephentown Hotel

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (137 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is CA $176
CA $197 total
includes taxes & fees
Feb 19 - Feb 20
Micosta Leisure Inn

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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 CA $146
CA $452 total
includes taxes & fees
Mar 2 - Mar 3
Near Tanglewood: Historic Summer Retreat

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is CA $186
CA $409 total
includes taxes & fees
Mar 4 - Mar 5
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 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 CA $211
CA $357 total
includes taxes & fees
Feb 23 - Feb 24
Home in Great Barrington

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is CA $244
CA $624 total
includes taxes & fees
Feb 22 - Feb 23
Sun Filled Lenox Retreat - Minutes to Tanglewood!

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (53 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is CA $133
CA $180 total
includes taxes & fees
Feb 16 - Feb 17
All comforts of home

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (10 reviews)
"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."
United States
Charles
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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 CA $237
CA $755 total
includes taxes & fees
Feb 22 - Feb 23
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is CA $533
CA $940 total
includes taxes & fees
Feb 17 - Feb 18
Guesthouse Cabin vacation rentals in Berkshire County

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is CA $144
CA $192 total
includes taxes & fees
Feb 19 - Feb 20
All the comforts of home

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (16 reviews)
"Nice Place"
United States
Tom C.
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
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

Find out more about Housatonic

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Housatonic. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: You might want to consider this vacation home rental near Housatonic, which offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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 selection of games and a hot tub.

How many vacation rentals will I find in Housatonic?

Expedia has 13 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.