Canann Village Historic District Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Canann Village Historic District holiday rentals

Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is HK$735
HK$4,891 total
includes taxes & fees
28 Dec - 29 Dec
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is HK$1,205
HK$2,006 total
includes taxes & fees
12 Jan - 13 Jan 2026
Home in Great Barrington
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$693
HK$1,311 total
includes taxes & fees
28 Dec - 29 Dec
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
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$3,058
HK$5,397 total
includes taxes & fees
4 Jan - 5 Jan 2026
Guesthouse Cabin vacation rentals in Berkshire County
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
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 HK$1,237
HK$1,569 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Brooks Motel: Exceptional Suite
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
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 HK$1,844
HK$3,911 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cheerful 3-bedroom cottage with woodstove
Games room
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
The price is HK$1,576
HK$2,316 total
includes taxes & fees
22 Dec - 23 Dec
Family Ski Getaway in the Berkshires
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
Goshen
The price is HK$1,856
HK$3,969 total
includes taxes & fees
23 Dec - 24 Dec
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Fridge, microwave, oven, stovetop
Catamount, Zip Line, Private Setting, Book Now!

Catamount, Zip Line, Private Setting, Book Now!

Catamount, Zip Line, Private Setting, Book Now!
Egremont
10.0 out of 10, Exceptional, (7)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
The price is HK$5,431
HK$11,262 total
includes taxes & fees
19 Jan - 20 Jan 2026
Catamount, Zip Line, Private Setting, Book Now!
Fridge, microwave, oven, stovetop
Modern Ranch Retreat in Hudson Valley

Modern Ranch Retreat in Hudson Valley

Modern Ranch Retreat in Hudson Valley
Millerton
10.0 out of 10, Exceptional, (4)
"Great communication and a fantastic property! The setting is quiet and short walk to downtown Millerton. The Harlem Valley Rail Trail Line is just down the road which offers excellent opportunities for adventures!"
United States
Scott E.
The price is HK$2,381
HK$4,278 total
includes taxes & fees
22 Dec - 23 Dec
Modern Ranch Retreat in Hudson Valley
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is HK$2,412
HK$4,311 total
includes taxes & fees
4 Jan - 5 Jan 2026
Great Barrington Get Away
Exterior detail
Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is HK$6,225
HK$9,435 total
includes taxes & fees
22 Dec - 23 Dec
Whispering Estate Guest House - A Romantic Countryside Getaway
Fridge, microwave, oven, stovetop
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
The price is HK$2,410
HK$3,005 total
includes taxes & fees
22 Dec - 23 Dec
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Outdoor dining
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Hillsdale
10.0 out of 10, Exceptional, (1)
"Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well "
United States
Gabrielle T.
The price is HK$3,431
HK$9,238 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (3)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,405
HK$10,335 total
includes taxes & fees
25 Dec - 26 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
The price is HK$6,598
HK$13,796 total
includes taxes & fees
18 Jan - 19 Jan 2026
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$2,646
HK$4,572 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4)
"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$1,237
HK$1,560 total
includes taxes & fees
22 Dec - 23 Dec
The Brooks Motel: Exceptional Suite
Fridge, microwave, stovetop, coffee/tea maker
Brooks Motel: Perfect Suite, Seasonal Waterviews

Brooks Motel: Perfect Suite, Seasonal Waterviews

Brooks Motel: Perfect Suite, Seasonal Waterviews
Hillsdale
6.0 out of 10, (1)
"NO HOT WATER!!! My room had exposed wood not like the photo. Musty smell in living room."
United States
Joan V.
The price is HK$1,120
HK$1,429 total
includes taxes & fees
22 Dec - 23 Dec
Brooks Motel: Perfect Suite, Seasonal Waterviews
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 Canann Village Historic District Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Yes"
Richard 3-night trip
Posted 2 days ago
The Red Lion Inn

Find out more about Canann Village Historic District

Search for holiday rentals in Canann Village Historic District on Expedia! You can easily find your home rentals, villas, holiday apartments in Canann Village Historic District using one of the methods below:

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Look no further and take a look at our great range of rental properties in Canann Village Historic District!

Frequently asked questions

Can I find holiday rentals in Canann Village Historic District?

Yes, there are holiday rentals close to the most popular sights in Canann Village Historic District, 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 Canann Village Historic District has to offer?

Family Ski Getaway in the Berkshires: This holiday home rental outside of Canann Village Historic District 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.

What’s there to see and do in Canann Village Historic District?

Explore the area and family-friendly sights such as Harney and Sons Tea Tasting Room, or get out into nature at a spot like Great Falls. Douglas Library and C H Pease Museum are other places to visit while you're in town.

What’s a holiday rental in Canann Village Historic District like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Canann Village Historic District. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for families.