Housatonic Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Housatonic vacation rentals

Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Vacation Home in Housatonic

10.0 out of 10, Exceptional, (3)
"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 ￥21,032
￥37,762 total
includes taxes & fees
Dec 11 - Dec 12
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.

Mobile Home in Chatham

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 ￥35,053
￥58,325 total
includes taxes & fees
Dec 16 - Dec 17
Sugar Shack - 300 square feet of pure sweetness.
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

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 ￥22,864
￥59,171 total
includes taxes & fees
Dec 15 - Dec 16
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
The price is ￥16,358
￥36,718 total
includes taxes & fees
Dec 11 - Dec 12
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

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 ￥15,003
￥33,438 total
includes taxes & fees
Dec 14 - Dec 15
Berkshires Apartment at the Stephentown Hotel
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

9.8 out of 10, Exceptional, (34)
"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 ￥27,945
￥68,875 total
includes taxes & fees
Dec 14 - Dec 15
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

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 ￥24,958
￥61,115 total
includes taxes & fees
Dec 15 - Dec 16
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is ￥20,465
￥36,172 total
includes taxes & fees
Dec 15 - Dec 16
Home in Great Barrington
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

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 ￥21,032
￥32,344 total
includes taxes & fees
Dec 11 - Dec 12
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

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 ￥16,358
￥36,718 total
includes taxes & fees
Dec 11 - Dec 12
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
TV, DVD player, books
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment in Hancock

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 ￥16,358
￥36,718 total
includes taxes & fees
Dec 11 - Dec 12
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥22,434
￥28,616 total
includes taxes & fees
Dec 12 - Dec 13
The Brooks Motel: Exceptional Suite
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

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 ￥28,750
￥32,114 total
includes taxes & fees
Dec 11 - Dec 12
Jiminy Peak Mountain Resort
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment in Hancock

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 ￥16,358
￥36,718 total
includes taxes & fees
Dec 11 - Dec 12
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Property grounds
All comforts of home

Apartment in Hudson

9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,283
￥20,605 total
includes taxes & fees
Dec 11 - Dec 12
All comforts of home
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Vacation Home in Lebanon Springs

8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is ￥21,032
￥57,580 total
includes taxes & fees
Dec 17 - Dec 18
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
All the comforts of home

Vacation Home in Hudson

9.2 out of 10, Wonderful, (28)
"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 ￥16,545
￥22,021 total
includes taxes & fees
Dec 11 - Dec 12
All the comforts of home
Indoor pool
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Apartment in Hancock

9.8 out of 10, Exceptional, (18)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
The price is ￥16,358
￥36,544 total
includes taxes & fees
Dec 15 - Dec 16
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

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 ￥36,922
￥78,308 total
includes taxes & fees
Dec 11 - Dec 12
Cheerful 3-bedroom cottage with woodstove
Terrace/patio
Pet-Friendly Hudson Escape w/ Hot Tub

Cottage in Stottville

2.0 star property
The price is ￥21,811
￥47,915 total
includes taxes & fees
Dec 15 - Dec 16
Pet-Friendly Hudson Escape w/ Hot Tub
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

Granville House

Granville House

10/10 Excellent
"Everything about Granville House is delightful. The owners have paid attention to every detail, from the decor and the way the rooms are appointed to the comfortable bed and the delicious hot breakfast."
Ann 1-night trip
Posted 2 days ago
Granville House

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
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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 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?

Pet Friendly Riverfront Home in Great Barrington: You might want to consider this vacation home rental near Housatonic, which 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 vacation with amenities like a selection of games.

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.