Default HTG hotel image

Holiday Rentals in Canann Village Historic District

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Canann Village Historic District holiday rentals

Property grounds

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €374
includes taxes & fees
28 Sept - 29 Sept
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is €146
includes taxes & fees
8 Oct - 9 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

3. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is €270
includes taxes & fees
15 Sept - 16 Sept
Home in Great Barrington
Interior

4. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is €196
includes taxes & fees
13 Sept - 14 Sept
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Terrace/patio

5. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is €327
includes taxes & fees
13 Sept - 14 Sept
Ideal location for summer and winter activities with plenty of outdoor space.
Beach nearby, sun-loungers, beach towels

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is €307
includes taxes & fees
14 Sept - 15 Sept
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Dining

7. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is €371
includes taxes & fees
13 Sept - 14 Sept
Art House 3 Beds Close to Warner Theater
Interior

8. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (25 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is €271
includes taxes & fees
23 Sept - 24 Sept
Riverside Retreat in the Berkshires
Outdoor dining

9. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is €216
includes taxes & fees
14 Sept - 15 Sept
Cozy Camper tucked into the woods
Interior

10. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is €274
includes taxes & fees
25 Sept - 26 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
TV, fireplace, books

11. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is €586
includes taxes & fees
15 Sept - 16 Sept
NEW: Chic Modern Barn Style Home in Fun Area
3 bedrooms, iron/ironing board, WiFi, bed sheets

12. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"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 €466
includes taxes & fees
14 Sept - 15 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV

13. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is €493
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
2 bedrooms, WiFi, bed sheets

14. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is €294
includes taxes & fees
14 Sept - 15 Sept
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Smart TV, books

15. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is €580
includes taxes & fees
13 Sept - 14 Sept
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Dining

16. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is €499
includes taxes & fees
13 Sept - 14 Sept
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
TV, fireplace, printers

17. 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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is €1,137
includes taxes & fees
18 Sept - 19 Sept
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

18. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is €728
includes taxes & fees
28 Sept - 29 Sept
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Coffee/tea maker, fridge, microwave, oven

19. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is €1,262
includes taxes & fees
25 Sept - 26 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Canann Village Historic District Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Check-in was easy and the desk staff efficient. Breakfast was good as expected and breakfast area clean. Unusual to have to fill out a form the night in advance if you wanted the room cleaned or fresh towels. Great location with good dining options close by."
Ronald 2-night trip
Posted 5 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Canann Village Historic District

Everything you need to know about Canann Village Historic District 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 Canann Village Historic District holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Canann Village Historic District holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Canann Village Historic District holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Canann Village Historic District. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Canann Village Historic District 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 Canann Village Historic District holiday rentals we have selected for you start as low as €146 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Canann Village Historic District rentals

At Expedia, we put the best Canann Village Historic District 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 Canann Village Historic District 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 Canann Village Historic District 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 Canann Village Historic District. 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 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?

The Meadows House @ Otis Ridge w/ 7-person hot tub: This holiday home rental outside of Canann Village Historic District is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.