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Canann Village Historic District Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Canann Village Historic District holiday rentals

Terrace/patio

1. 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, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AU$302
includes taxes & fees
19 Aug - 20 Aug
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Coffee/tea maker, fridge, microwave, oven

2. 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 AU$582
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Desk, iron/ironing board, WiFi, bed sheets

3. 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$273
includes taxes & fees
12 Aug - 13 Aug
The Brooks Motel: Exceptional Suite
Beach nearby, sun-loungers, beach towels

4. 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 AU$432
includes taxes & fees
8 Sept - 9 Sept
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
2 bedrooms, free WiFi, 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 AU$328
includes taxes & fees
24 Aug - 25 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

6. 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 AU$451
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
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 AU$609
includes taxes & fees
12 Aug - 13 Aug
Art House 3 Beds Close to Warner Theater
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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$437
includes taxes & fees
3 Sept - 4 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

9. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (130 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AU$751
includes taxes & fees
13 Aug - 14 Aug
Gorgeous Mountain Views Retreat: Family & Nature
TV

10. 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 AU$873
includes taxes & fees
2 Sept - 3 Sept
Treetop Hideaway in Tyringham
Desk, iron/ironing board, WiFi, bed sheets

11. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (6 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 AU$287
includes taxes & fees
12 Aug - 13 Aug
The Brooks Motel: Exceptional Suite
Dining

12. 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$720
includes taxes & fees
12 Aug - 13 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
3 bedrooms, iron/ironing board, WiFi, bed sheets

13. 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 AU$930
includes taxes & fees
8 Sept - 9 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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, (2 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 AU$983
includes taxes & fees
19 Aug - 20 Aug
NEW: Chic Modern Barn Style Home in Fun Area
TV, fireplace, printers

15. 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 AU$1,829
includes taxes & fees
13 Aug - 14 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor dining

16. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is AU$871
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Coffee/tea maker, fridge, microwave, oven

17. 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 AU$2,028
includes taxes & fees
17 Aug - 18 Aug
A Country Lodge Straight Out of the Pages of a Great Novel
Interior

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

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is AU$472
includes taxes & fees
31 Aug - 1 Sept
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"The Holiday Inn Resort in Lee, MA was a GREAT VALUE compared to the five other lodging options in which I've stayed that were proximal to Tanglewood. I'd gladly stay here again, but would try a different location in the resort. Benefits: a well-provisioned kitchen, generously-sized balcony, pleasant and helpful staff, nice pools and other activities, free laundry, convenient parking and private jacuzzi. The unit's approx. 880 sq ft 2 bedroom, 2 bath space was quiet and comfortable for two people over our 9-night stay and the 2-flight walk-up was OK for two fairly fit 70-year-olds. Bedroom storage was on the low side but OK for us. One of us found the beds a bit too soft, for the other they were fine. Decor was modest & well-maintained. Unlike other reviews, we were on the lookout but didn't see any bears! Good to know: We didn't realize until our arrival that bedding and towels are only changed every 10 days. However, on arrival extra towels and one change of sheets were already provided, which were more than adequate for our needs. Drawbacks: if you want high-end decor, maybe try the Presidential Suites. There was evidence of insect damage on the exterior wood stairs, unattractive but not unsafe. The low-lying property is near water and a bit damp. Our lodging in building 24 was near the maintenance yard, trash disposal and ongoing bridge repair (about which we weren't forewarned). Since we were out during most days, none of these drawbacks affected us."
Loreen 9-night trip
Posted 4 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

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$328 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 kitchenware, 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 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.