Canann Village Historic District Holiday Rentals from NZ$277: Search Short-Term Rentals

Q: 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.

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Our top choices for Canann Village Historic District holiday rentals

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

bob i.

includes taxes & fees

8 Sept - 9 Sept

2. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

22 Sept - 23 Sept

3. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted

Steve

includes taxes & fees

1 Sept - 2 Sept

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

Winchester

includes taxes & fees

1 Sept - 2 Sept

5. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

3 Sept - 4 Sept

Desk, iron/ironing board, WiFi, bed sheets

6. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

1 Sept - 2 Sept

7. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

9 Sept - 10 Sept

Beach nearby, sun-loungers, beach towels

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

Great Barrington

Kristin O.

includes taxes & fees

14 Sept - 15 Sept

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

Housatonic

Peter S.

includes taxes & fees

3 Sept - 4 Sept

10. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

includes taxes & fees

15 Sept - 16 Sept

3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Great Barrington

Mary R.

includes taxes & fees

8 Sept - 9 Sept

12. Treetop Hideaway in Tyringham

Monterey

"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!! "

Samantha G.

includes taxes & fees

21 Sept - 22 Sept

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

Otis

includes taxes & fees

7 Sept - 8 Sept

14. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

includes taxes & fees

30 Aug - 31 Aug

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

Hillsdale

includes taxes & fees

30 Aug - 31 Aug

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

Torrington

Jaimie S.

includes taxes & fees

22 Sept - 23 Sept

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

Pine Plains

Estefany G.

includes taxes & fees

22 Sept - 23 Sept

18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Rebecca K.

includes taxes & fees

30 Aug - 31 Aug

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

Stockbridge

Anonymous traveller

includes taxes & fees

28 Sept - 29 Sept

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

Pine Plains

Hessie S.

includes taxes & fees

9 Sept - 10 Sept

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Top Canann Village Historic District Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Amazing time. Stayed in the Presidential units. Worth it."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"It was much better than expected. Subtle lighting in the room was a nice touch. Clean and very comfortable bedding and bathroom. Everything in the fitness room was was clean and operational. The breakfast was superb. A very enjoyable stay."

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 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 NZ$277 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?

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.

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Check prices for these dates

Our top choices for Canann Village Historic District holiday rentals

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

2. Cheerful 3-bedroom cottage with woodstove

3. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

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

5. Home in Great Barrington

6. The Brooks Motel: Exceptional Suite

7. Cozy Riverside Berkshires Retreat

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

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

10. Art House 3 Beds Close to Warner Theater

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

12. Treetop Hideaway in Tyringham

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

14. The Brooks Motel: Exceptional Suite

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

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

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

18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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

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

Find holiday rentals that suit your style

Top Canann Village Historic District Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Red Lion Inn

Hitching Post Country Motel

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Little Lion

Holiday Inn Express Hotel & Suites Great Barrington by IHG

the Alander

Blackberry River Inn

Locust Tree Bed and Breakfast LLC

Find out more about Canann Village Historic District

Frequently asked questions

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