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Canann Village Historic District Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Canann Village Historic District vacation rentals

Coffee/tea maker, fridge, microwave, oven

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is AED 380
AED 568 total
includes taxes & fees
31 Aug - 1 Sep
Cozy 1-bedroom studio in serene Great Barrington with AC
Property grounds

2. 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 AED 907
AED 1,908 total
includes taxes & fees
22 Sep - 23 Sep
Cheerful 3-bedroom cottage with woodstove
Terrace/patio

3. 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
9.4 out of 10, Exceptional, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AED 463
AED 885 total
includes taxes & fees
31 Aug - 1 Sep
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Desk, iron/ironing board, WiFi, bed sheets

4. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is AED 551
AED 708 total
includes taxes & fees
23 Aug - 24 Aug
The Brooks Motel: Exceptional Suite
2 bedrooms, WiFi (free), bed sheets

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 456
AED 828 total
includes taxes & fees
30 Aug - 31 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Coffee/tea maker, fridge, microwave, oven

6. 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 AED 992
AED 1,502 total
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Beach nearby, sun loungers, beach towels

7. 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, (3 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 AED 856
AED 1,317 total
includes taxes & fees
13 Sep - 14 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Dining

8. 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 AED 516
AED 1,595 total
includes taxes & fees
1 Sep - 2 Sep
Art House 3 Beds Close to Warner Theater
Interior

9. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 744
AED 1,155 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Riverside Berkshires Retreat
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 AED 643
AED 1,169 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Desk, iron/ironing board, WiFi, bed sheets

11. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.6 out of 10, Excellent, (7 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is AED 580
AED 745 total
includes taxes & fees
23 Aug - 24 Aug
The Brooks Motel: Exceptional Suite
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 AED 1,171
AED 2,046 total
includes taxes & fees
1 Sep - 2 Sep
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 AED 1,036
AED 2,139 total
includes taxes & fees
21 Sep - 22 Sep
Treetop Hideaway in Tyringham
TV, fireplace, books

14. 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 AED 1,006
AED 2,899 total
includes taxes & fees
24 Aug - 25 Aug
NEW: Chic Modern Barn Style Home in Fun Area
Dining

15. 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 AED 859
AED 1,914 total
includes taxes & fees
23 Aug - 24 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Exterior

16. Family home by Polo fields with great yard & game rm. EV charger, pet friendly!

Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
Pine Plains
10.0 out of 10, Exceptional, (7 reviews)
"It felt clean, comfortable, accomodating, and most important, safe. Our family had an amazing time here and we will definitely visit again. Thank you!"
United States
Jon W.
The price is AED 1,388
AED 2,983 total
includes taxes & fees
26 Aug - 27 Aug
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
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)
"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 AED 2,079
AED 4,874 total
includes taxes & fees
24 Aug - 25 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Smart TV, books

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

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AED 1,483
AED 2,488 total
includes taxes & fees
23 Aug - 24 Aug
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Outdoor dining

19. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
Stockbridge In-town Escape
Coffee/tea maker, fridge, microwave, oven

20. 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 AED 3,269
AED 5,410 total
includes taxes & fees
24 Aug - 25 Aug
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.
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Top Canann Village Historic District Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Evan M 1-night trip
Posted less than an hour ago
The Red Lion Inn

Frequently asked questions

Can I find vacation rentals in Canann Village Historic District?

Yes, we have vacation rentals near top sights in Canann Village Historic District, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Canann Village Historic District has to offer?

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Canann Village Historic District is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 vacation rental in Canann Village Historic District like?

Vacation rentals are private properties you can stay in for a long or short time in Canann Village Historic District. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family getaway.