The Best Canaan, NY Chalets from $76

Check prices for these dates

In two weeks

In two months

In three months

In four months

No exact matches found, but these alternatives could be just right

Recommended hotels in Canaan

1. Inn at Silver Maple Farm

East Chatham

Erdem

$139 nightly

Sep 1 - Sep 2

Total with taxes and fees

2. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Jermaine

$115 nightly

Sep 20 - Sep 21

Total with taxes and fees

3. The Yankee Inn

Lenox

Karen

$86 nightly

Sep 28 - Sep 29

Total with taxes and fees

4. Berkshire Travel Lodge

Austerlitz

Kris

$67 nightly

Sep 27 - Sep 28

Total with taxes and fees

5. Howard Johnson by Wyndham Lenox

Lenox

Sheila

$78 nightly

Sep 13 - Sep 14

Total with taxes and fees

6. Berkshire Mountain Lodge

Pittsfield

Robert

$108 nightly

Oct 1 - Oct 2

Total with taxes and fees

7. Shaker Mill Inn

West Stockbridge

Mervin

$153 nightly

Sep 8 - Sep 9

Total with taxes and fees

8. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

$123 nightly

Sep 13 - Sep 14

Total with taxes and fees

9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Steve

$118 nightly

Sep 8 - Sep 9

Total with taxes and fees

10. Chatham Travel Lodge

Old Chatham

Andrew

$112 nightly

Sep 8 - Sep 9

Total with taxes and fees

11. Pleasant Valley Motel West Stockbridge

West Stockbridge

Peter

$72 nightly

Sep 1 - Sep 2

Total with taxes and fees

12. Berkshires Untold

Lenox

Christine

$145 nightly

Sep 28 - Sep 29

Total with taxes and fees

13. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Rinat

$128 nightly

Sep 21 - Sep 22

Total with taxes and fees

Hypo-allergenic bedding available, desk, laptop workspace

14. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

$118 nightly

Sep 7 - Sep 8

Total with taxes and fees

15. The Red Lion Inn

Stockbridge

Patricia

$212 nightly

Sep 8 - Sep 9

Total with taxes and fees

16. Berkshire Inn

Pittsfield

Adriana

$86 nightly

Sep 1 - Sep 2

Total with taxes and fees

17. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

$148 nightly

Sep 13 - Sep 14

Total with taxes and fees

18. Quality Inn Lee - Lenox South

Lee

Christine

$110 nightly

Sep 20 - Sep 21

Total with taxes and fees

19. Courtyard by Marriott Lenox Berkshires

Lenox

Laura

$178 nightly

Sep 7 - Sep 8

Total with taxes and fees

Premium bedding, pillowtop beds, in-room safe, desk

20. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

BJORN

$115 nightly

Sep 7 - Sep 8

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Canaan Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Clean & comfortable stay"

Vacation Village in the Berkshires

10/10 Excellent

"STOP your search now. Vacation Village is THE place to stay if you're visiting the Berkshires, any time of year. The staff are all absolutely wonderful and dedicated to making sure all guests are 100% satisfied. Brad, the manager is kind and incredibly efficient, always on top of things. The rooms, are all spacious, and the porch/balcony are great and really set the property apart from others. Beds, Couches, linens, all comfortable, kitchen well stocked, parking is always a breeze. Pools are always clean, grounds clean and well maintained. I wouldnt stay anywhere else. It definitely feels like a village 😄Easy access to fun and necessities. Dont forget to hop over the line into New York, its worth a slow morning drive."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Pocketbook Hotel and Bath

8/10 Good

"Gorgeous stay - need to work out some kinks. Had to ask for a steamer 3 times to never get one. 3 times for extra pillows. The valet parking situation is a bit off. Hotel staff talking loudly with non guests how they wouldn’t spend the money to stay here. Our room had a window that was directly in the way of morning light with a window that had NO shade - brought this up and nothing was done nor apologized. The rooms are LOUD - yes the property is old and they make note but when you have old and steel tubs you need to add rugs in the room minimum. The aesthetic is beautiful and the design firm did great but if you want to charge these prices that I’m sure will climb you need to fix these small details. The restaurant was the star out our trip absolutely incredible food and lovely staff. Overall a good stay but again - some changes need to be made as you know the crowd you are attracting."

Quality Inn Lee - Lenox South

8/10 Good

"Very nice and clean motel...better than I thought it would be, so we felt a lot better about staying there. We were a bit disappointed about the breakfast portion of the day so went out for brunch instead. The breakfast sandwiches weren't that great and not many tables to sit at. But overall, the rooms and bathrooms were very clean and modern."

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

Find out more about Canaan

Canaan Chalets information

Number of reviews	11,200
Accommodation	6 Chalets
Lowest Price	$76
Highest Price	$198

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Recommended hotels in Canaan

1. Inn at Silver Maple Farm

2. Best Western Plus Berkshire Hills Inn & Suites

3. The Yankee Inn

4. Berkshire Travel Lodge

5. Howard Johnson by Wyndham Lenox

6. Berkshire Mountain Lodge

7. Shaker Mill Inn

8. Hampton Inn & Suites Berkshires-Lenox

9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10. Chatham Travel Lodge

11. Pleasant Valley Motel West Stockbridge

12. Berkshires Untold

13. The Black Swan Lee - Lenox, an Ascend Collection Hotel

14. Holiday Inn & Suites Pittsfield-Berkshires by IHG

15. The Red Lion Inn

16. Berkshire Inn

17. Hilton Garden Inn Lenox Pittsfield

18. Quality Inn Lee - Lenox South

19. Courtyard by Marriott Lenox Berkshires

20. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find vacation rentals that suit your style

Top Canaan Hotel Reviews

Berkshire Mountain Lodge

Vacation Village in the Berkshires

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Pocketbook Hotel and Bath

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jiminy Peak Mountain Resort

Berkshires Untold

Find out more about Canaan

Canaan Chalets information

Explore a world of travel with Expedia