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Housatonic Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Housatonic holiday rentals

Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Holiday Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,134
HK$2,908 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Holiday Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is HK$1,246
HK$3,050 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
The price is HK$1,050
HK$1,606 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop
Home in Great Barrington

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"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$1,176
HK$1,999 total
includes taxes & fees
6 Jan - 7 Jan 2026
Home in Great Barrington
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,669
HK$1,865 total
includes taxes & fees
4 Jan - 5 Jan 2026
Jiminy Peak Mountain Resort
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"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 HK$957
HK$1,898 total
includes taxes & fees
3 Jan - 4 Jan 2026
Berkshires Apartment at the Stephentown Hotel
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is HK$1,610
HK$3,691 total
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Holiday Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is HK$1,166
HK$3,039 total
includes taxes & fees
13 Jan - 14 Jan 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Holiday Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is HK$1,400
HK$3,578 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Property grounds
All comforts of home

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$763
HK$1,028 total
includes taxes & fees
29 Dec - 30 Dec
All comforts of home
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is HK$1,253
HK$3,006 total
includes taxes & fees
22 Jan - 23 Jan 2026
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Apartment in Hancock

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
9.8 out of 10, Exceptional, (7)
"Everything was wonderful…"
United States
Alyne K.
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is HK$2,006
HK$3,257 total
includes taxes & fees
26 Dec - 27 Dec
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Property grounds
All the comforts of home

Holiday Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is HK$826
HK$1,099 total
includes taxes & fees
31 Dec - 1 Jan 2026
All the comforts of home
Property grounds
Cheerful 3-bedroom cottage with woodstove

Holiday Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,843
HK$3,909 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cheerful 3-bedroom cottage with woodstove
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

Charming 3-bedroom Cabin for nature lovers
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is HK$1,205
HK$2,486 total
includes taxes & fees
28 Dec - 29 Dec
Charming 3-bedroom Cabin for nature lovers
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment in Hancock

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
TV, DVD player, books
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment in Hancock

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3)
"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
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"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$3,056
HK$5,246 total
includes taxes & fees
4 Jan - 5 Jan 2026
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Holiday Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is HK$2,092
HK$3,840 total
includes taxes & fees
5 Jan - 6 Jan 2026
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Perfect for a weekend away. Stagg was friendly. Room was clean and spacious. It was everything we needed and more."
Cynthia 2-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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
  • Use the map to find apartments and other holiday homes in the Housatonic neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Housatonic while they last

Look no further and take a look at our great range of rental properties in Housatonic!

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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?

Peace and quiet on the lake: This holiday home rental outside of Housatonic is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Housatonic?

Expedia has 13 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 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 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.