Housatonic Holiday Rentals

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Our top choices for Housatonic holiday rentals

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 AU$572
includes taxes & fees
5 Jan - 6 Jan 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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 AU$600
includes taxes & fees
5 Jan - 6 Jan 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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 AU$316
includes taxes & fees
23 Dec - 24 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is AU$393
includes taxes & fees
5 Jan - 6 Jan 2026
Home in Great Barrington

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 AU$370
includes taxes & fees
4 Jan - 5 Jan 2026
Jiminy Peak Mountain Resort
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 AU$347
includes taxes & fees
23 Dec - 24 Dec
Berkshires Apartment at the Stephentown Hotel
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 AU$736
includes taxes & fees
5 Jan - 6 Jan 2026
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is AU$592
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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 AU$704
includes taxes & fees
4 Jan - 5 Jan 2026
Sun Filled Lenox Retreat - Minutes to Tanglewood!

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 AU$203
includes taxes & fees
23 Dec - 24 Dec
All comforts of home
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is AU$545
includes taxes & fees
23 Dec - 24 Dec
UNIQUE - 1BR Country Condo @ Jiminy Peak
9.8 out of 10, Exceptional, (7)
"Everything was wonderful…"
United States
Alyne K.
The price is AU$425
includes taxes & fees
23 Dec - 24 Dec
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
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 AU$495
includes taxes & fees
23 Dec - 24 Dec
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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 AU$217
includes taxes & fees
23 Dec - 24 Dec
All the comforts of home
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 AU$768
includes taxes & fees
5 Jan - 6 Jan 2026
Cheerful 3-bedroom cottage with woodstove
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 AU$492
includes taxes & fees
23 Dec - 24 Dec
Charming 3-bedroom Cabin for nature lovers
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AU$425
includes taxes & fees
23 Dec - 24 Dec
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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.
The price is AU$480
includes taxes & fees
23 Dec - 24 Dec
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
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 AU$1,061
includes taxes & fees
4 Jan - 5 Jan 2026
Guesthouse Cabin vacation rentals in Berkshire County
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 AU$755
includes taxes & fees
3 Jan - 4 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

Find out more about Housatonic

Everything you need to know about Housatonic holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Housatonic holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Housatonic holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Housatonic holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Housatonic. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Housatonic holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Housatonic holiday rentals we have selected for you start as low as AU$220 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Housatonic rentals

At Expedia, we put the best Housatonic holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Housatonic rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Housatonic holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Housatonic. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Housatonic is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.