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Canann Village Historic District Holiday Rentals

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Our top choices for Canann Village Historic District holiday rentals

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, (77 reviews)
"Excellent host!"
United States
Kenny
The price is AU$549
includes taxes & fees
30 June - 1 July
Ideal location for summer and winter activities with plenty of outdoor space.

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"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 AU$1,004
includes taxes & fees
29 June - 30 June
Guesthouse Cabin vacation rentals in Berkshire County

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$477
includes taxes & fees
1 July - 2 July
Cozy Riverside Berkshires Retreat

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 AU$599
includes taxes & fees
28 June - 29 June
Art House 3 Beds Close to Warner Theater

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, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AU$369
includes taxes & fees
2 July - 3 July
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveller
The price is AU$618
includes taxes & fees
19 July - 20 July
Home in Great Barrington

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$935
includes taxes & fees
29 June - 30 June
Treetop Hideaway in Tyringham

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is AU$1,259
includes taxes & fees
5 July - 6 July
Whispering Estate Guest House - A Romantic Countryside Getaway

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 AU$794
includes taxes & fees
5 July - 6 July
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

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 AU$717
includes taxes & fees
28 June - 29 June
Cheerful 3-bedroom cottage with woodstove

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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 AU$675
includes taxes & fees
29 June - 30 June
Sweet Cozy Victorian in Housatonic. Close to everything.

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 AU$279
includes taxes & fees
28 June - 29 June
The Brooks Motel: Exceptional Suite

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, (6 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 AU$1,901
includes taxes & fees
29 June - 30 June
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is AU$572
includes taxes & fees
3 July - 4 July
Litchfield Retreat, Wineries, Foliage & Skiing

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, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AU$1,541
includes taxes & fees
19 July - 20 July
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Historic South Lee Apt 2 Mi to Main Street

Historic South Lee Apt 2 Mi to Main Street
South Lee
The price is AU$1,955
includes taxes & fees
28 June - 29 June
Historic South Lee Apt 2 Mi to Main Street

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is AU$1,014
includes taxes & fees
29 June - 30 June
NEW: Chic Modern Barn Style Home in Fun Area

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 AU$1,206
includes taxes & fees
5 July - 6 July
Perfect House In Hillsdale, Brings Friends & Fam

Perfect Nature Haven In Great Barrington

Perfect Nature Haven In Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (8 reviews)
"Their place was one of the cleanest rental cabins we have ever been, the house is in a great location with beautiful surroundings, the check in and check out was extremely easy for a family with little kids, loved the place and we hope to be back!"
United States
Ethel B.
The price is AU$2,811
includes taxes & fees
5 July - 6 July
Perfect Nature Haven In Great Barrington

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, (13 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 AU$2,054
includes taxes & fees
14 July - 15 July
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

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, 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 favourite 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 depend 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 AU$477 per night. Entering your travel dates in the search wizard might find you 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?

Cozy Riverside Berkshires Retreat: This holiday 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 an electric kettle, so that you can cook with friends or family. 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 Mount Frissell. 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.