The Best Craryville, NY Chalets from $74

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Recommended hotels in Craryville

A covered porch with a wooden floor, white railings, and hanging flower baskets.

1. Changing Times Boutique Country Lodging

Craryville

Thomas

$200 nightly

Nov 6 - Nov 7

Total with taxes and fees

A Quality Inn sign, a brick building, and a parking lot with cars.

2. Quality Inn Great Barrington

Downtown Great Barrington

Lynne

$76 nightly

Nov 29 - Nov 30

Total with taxes and fees

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

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

Great Barrington

Cynthia

$90 nightly

Nov 30 - Dec 1

Total with taxes and fees

A house with a stone patio and wooden stools.

4. Little Cat Lodge

Copake Falls

Stacy

$147 nightly

Dec 6 - Dec 7

Total with taxes and fees

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

5. the Alander

Copake

Luis

$165 nightly

Nov 20 - Nov 21

Total with taxes and fees

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

6. Monument Mountain Motel

Great Barrington

Andrea

$67 nightly

Nov 8 - Nov 9

Total with taxes and fees

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Md

$161 nightly

Nov 10 - Nov 11

Total with taxes and fees

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

8. Prospect Berkshires

Egremont

Sunny

$295 nightly

Nov 30 - Dec 1

Total with taxes and fees

A wooden deck with two chairs and a table, overlooking a lush green landscape and a golf course.

9. Micosta Leisure Inn

Hudson

George

$113 nightly

Nov 9 - Nov 10

Total with taxes and fees

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

10. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Sherry

$79 nightly

Nov 6 - Nov 7

Total with taxes and fees

A two-story building with a gabled roof and a chimney.

11. The Little Lion

Great Barrington

David

$86 nightly

Nov 8 - Nov 9

Total with taxes and fees

A two-story building with a brick facade and a flat roof.

12. Howard Hotel

Hudson

zehava

$114 nightly

Dec 6 - Dec 7

Total with taxes and fees

A large brick building with multiple arched windows and a central chimney.

13. Pocketbook Hotel and Bath

Hudson

Judith and Robert

$240 nightly

Dec 6 - Dec 7

Total with taxes and fees

A balcony with two white chairs and a blue and white striped rug.

14. Nautical Nest

Hudson

Christina

$118 nightly

Dec 6 - Dec 7

Total with taxes and fees

A motel with a gravel driveway leading to a parking area, surrounded by lush green trees and a clear blue sky.

15. East Rock Inn

Great Barrington

Sharon

$116 nightly

Dec 6 - Dec 7

Total with taxes and fees

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

16. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Saugerties

Jacqueline

$127 nightly

Nov 9 - Nov 10

Total with taxes and fees

A covered porch with a white door and windows, a small mailbox, and a number '330' on the wall.

17. The Nest Hudson

Hudson

Lisa

$117 nightly

Nov 16 - Nov 17

Total with taxes and fees

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

18. The Red Lion Inn

Stockbridge

Mallory

$195 nightly

Nov 12 - Nov 13

Total with taxes and fees

A red cabin with a screened porch, a small deck, and a barbecue grill in a wooded area.

19. Ideal location for summer and winter activities with plenty of outdoor space.

Hillsdale

Richard M.

$307 nightly

Nov 8 - Nov 9

Total with taxes and fees

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

Gustavo

$108 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Learn more about Craryville

Escape to Craryville! Enjoy its wildlife and food.

See all hotels in Craryville

A misty forest landscape with a hill in the background.

Top reviews in Craryville

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

Changing Times Boutique Country Lodging

Craryville

10/10 Excellent

Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.

Kathleen

Quality Inn Great Barrington

Downtown Great Barrington

10/10 Excellent

Andrew

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

Monument Mountain Motel

Great Barrington

10/10 Excellent

We have stayed here a half dozen times, and if you are simply looking for a clean place to lay your head for the night with no frills, then this place is perfect! The rooms have always been clean and everything in good working order. So what that they don't have breakfast...there is an AMAZING breakfast spot right across the street. Take HALF the money you saved by avoiding big name hotels and you'll get a much better breakfast! We've never had noise issues, never felt "unsafe", and the staff is...

Anthony

The Nest Hudson

Hudson

10/10 Excellent

The Nest Hotel is a lovely place that is well situated within walking distance to shops, restaurants, and the river. The room was very comfortable and well appointed and they had a small, but well stocked kitchen with coffee, espresso, and small snacks. Hudson is a beautiful area and perfect for a fall weekend. My sister and I appreciated the hotel's recommendations and the self check-in/check-out instructions were easy to follow. The only downside was that the house next door was under...

Felicia

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe