Housatonic Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Housatonic holiday rentals

Interior

Holiday Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
10.0 out of 10, Exceptional, (4 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 HK$1,056
HK$2,097 total
includes taxes & fees
3 Mar - 4 Mar
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is HK$1,479
HK$2,515 total
includes taxes & fees
10 Mar - 11 Mar
BLUSH: Boutique TINY home*private spa*walk to town
Dining

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is HK$1,447
HK$2,523 total
includes taxes & fees
3 Mar - 4 Mar
Sugar Shack - 300 square feet of pure sweetness.
Smart TV, books

Holiday Home in Sherwood Forest

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
9.8 out of 10, Exceptional, (14 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 HK$1,253
HK$3,086 total
includes taxes & fees
12 Mar - 13 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

Apartment in Hancock

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is HK$876
HK$1,888 total
includes taxes & fees
3 Mar - 4 Mar
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in 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 HK$1,260
HK$2,107 total
includes taxes & fees
3 Mar - 4 Mar
Home in Great Barrington
Gift shop

Apartment in Hancock

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is HK$845
HK$1,853 total
includes taxes & fees
4 Mar - 5 Mar
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Gift shop

Apartment in Hancock

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is HK$821
HK$1,818 total
includes taxes & fees
4 Mar - 5 Mar
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Interior

Holiday Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,267
HK$3,067 total
includes taxes & fees
1 Apr - 2 Apr
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior

Apartment in Hancock

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (11 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
The price is HK$829
HK$1,826 total
includes taxes & fees
4 Mar - 5 Mar
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
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 HK$3,129
HK$5,479 total
includes taxes & fees
3 Mar - 4 Mar
Guesthouse Cabin vacation rentals in Berkshire County
Exterior detail

Holiday Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is HK$1,408
HK$2,403 total
includes taxes & fees
3 Mar - 4 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

Holiday Home in Hudson

All the comforts of home
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 HK$831
HK$1,106 total
includes taxes & fees
3 Mar - 4 Mar
All the comforts of home
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$2,011
HK$4,195 total
includes taxes & fees
30 Mar - 31 Mar
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,244
HK$1,568 total
includes taxes & fees
3 Mar - 4 Mar
The Brooks Motel: Exceptional Suite
Property grounds

Apartment in Hudson

All comforts of home
9.6 out of 10, Exceptional, (54 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$767
HK$1,035 total
includes taxes & fees
3 Mar - 4 Mar
All comforts of home
Exterior

Apartment in Hancock

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
10.0 out of 10, Exceptional, (2 reviews)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
The price is HK$829
HK$1,826 total
includes taxes & fees
4 Mar - 5 Mar
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Exterior

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
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 HK$887
HK$2,694 total
includes taxes & fees
8 Mar - 9 Mar
Near Tanglewood: Historic Summer Retreat
Pool

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
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.
The price is HK$829
HK$1,826 total
includes taxes & fees
4 Mar - 5 Mar
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Indoor pool

Apartment in Hancock

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
9.8 out of 10, Exceptional, (22 reviews)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is HK$821
HK$1,818 total
includes taxes & fees
4 Mar - 5 Mar
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Clean, friendly staff, quiet, great breakfast, easy to get anywhere locally, updated!"
Joy 1-night trip
Posted 3 days ago
Best Western Plus Berkshire Hills Inn & Suites

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:

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Frequently asked questions

Can I find holiday rentals in Housatonic?

Yes, there are holiday rentals close to the most popular sights in Housatonic, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Housatonic has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Housatonic is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Housatonic?

Expedia has 12 holiday rentals for your stay in Housatonic.

What’s there to see and do in Housatonic?

While exploring the area, visit family-friendly sights like The Bookstore, 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 wider area.

What’s a holiday rental in Housatonic like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Housatonic. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.