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Canann Village Historic District Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Canann Village Historic District vacation rentals

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is SAR 666
SAR 1,603 total
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (8 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is SAR 338
SAR 524 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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, (55 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is SAR 473
SAR 893 total
includes taxes & fees
13 Oct - 14 Oct
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is SAR 432
SAR 791 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is SAR 835
SAR 1,305 total
includes taxes & fees
13 Oct - 14 Oct
Home in Great Barrington
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

6. 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 SAR 563
SAR 715 total
includes taxes & fees
11 Oct - 12 Oct
The Brooks Motel: Exceptional Suite
A sandy beach with a lake and forest in the background.

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, (6 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is SAR 785
SAR 1,233 total
includes taxes & fees
12 Oct - 13 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

8. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is SAR 1,283
SAR 2,188 total
includes taxes & fees
10 Nov - 11 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A staircase with a wooden handrail and a white wall with a light switch.

9. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 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 SAR 732
SAR 1,154 total
includes taxes & fees
29 Oct - 30 Oct
Leaf-Peeper Paradise in the Berkshires
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

10. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is SAR 602
SAR 756 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Camper tucked into the woods
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

11. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is SAR 920
SAR 2,118 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
A wooden cabin with a porch, a grill, and a flower planter.

12. 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 SAR 788
SAR 1,484 total
includes taxes & fees
13 Oct - 14 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 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 SAR 751
SAR 1,317 total
includes taxes & fees
13 Oct - 14 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

14. 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 SAR 537
SAR 1,643 total
includes taxes & fees
1 Nov - 2 Nov
Art House 3 Beds Close to Warner Theater
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

15. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 SAR 1,018
SAR 2,120 total
includes taxes & fees
9 Nov - 10 Nov
Treetop Hideaway in Tyringham
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is SAR 1,502
SAR 2,608 total
includes taxes & fees
20 Oct - 21 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

17. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 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 SAR 593
SAR 757 total
includes taxes & fees
20 Oct - 21 Oct
The Brooks Motel: Exceptional Suite
A two-story house with a front porch, surrounded by lush greenery and trees.

18. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is SAR 1,247
SAR 2,668 total
includes taxes & fees
11 Oct - 12 Oct
Perfect House In Hillsdale, Brings Friends & Fam
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

19. 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.
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

20. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
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 SAR 913
SAR 2,852 total
includes taxes & fees
29 Oct - 30 Oct
Chic Barn Style * Fireplace * Near Stissing House
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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"Excellent room! Clean and good breakfast!"
Kelly 1-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This vacation home rental outside of Canann Village Historic District offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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.