Craryville Holiday Rentals, New York: Private House Rentals

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Our top choices for Craryville hotels

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

A room with a white door, a window, and a wall with various framed pictures.

A two-story house with a porch, a front door, and a mailbox.

A traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

1. Changing Times Boutique Country Lodging

Craryville

Thomas

฿6,575

฿7,364 total

includes taxes & fees

31 Aug - 1 Sept

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

2. Little Cat Lodge

Copake Falls

Kees

฿5,888

฿6,594 total

includes taxes & fees

31 Aug - 1 Sept

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

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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

Great Barrington

Lisa

฿5,269

฿5,885 total

includes taxes & fees

8 Sept - 9 Sept

A modern hotel lobby with seating areas, tables, and a reception desk.

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

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

A hotel reception area with a check-in counter, a Holiday Inn Express sign, and a beverage refrigerator.

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

Great Barrington

฿3,780

฿4,223 total

includes taxes & fees

7 Sept - 8 Sept

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

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

5. the Alander

Copake

Phil

฿5,576

฿6,245 total

includes taxes & fees

2 Sept - 3 Sept

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

A dining area with a wooden table, chairs, and a colorful striped rug.

A snow-covered landscape with a house and a sign that reads "the brooks".

6. The Brooks Motel

Hillsdale

Nelson

฿4,793

฿5,368 total

includes taxes & fees

30 Aug - 31 Aug

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

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

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

7. Quality Inn Great Barrington

Great Barrington

Sisile

฿3,039

฿3,394 total

includes taxes & fees

24 Sept - 25 Sept

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

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

8. Prospect Berkshires

Egremont

Kellee

฿10,007

฿12,280 total

includes taxes & fees

27 Sept - 28 Sept

A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

A staircase with a wooden handrail and a wall with three framed paintings of forest scenes.

A room with two yellow armchairs, a small table with a lamp, a framed painting on the wall, and a window with curtains.

A cozy living room with a dark blue sofa, patterned armchair, and a wooden fireplace.

9. Inn at Pine Plains

Pine Plains

Mary

฿9,019

฿10,203 total

includes taxes & fees

30 Aug - 31 Aug

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

A wooden deck with a staircase leading to a covered porch.

A bedroom with a bed, a desk, a chair, a ceiling fan, and a view of the outdoors.

A cozy living room with a gray sofa, wooden ceiling beams, a black TV stand, and a dining area with a table and chairs.

10. Micosta Leisure Inn

Hudson

Andrea

฿4,253

฿4,764 total

includes taxes & fees

30 Aug - 31 Aug

A modern kitchen with a built-in oven, microwave, and stainless steel range hood.

A modern interior with a round mirror reflecting a dining area, a large vase, and a guitar.

A hallway with a staircase, a framed painting, a mirror, and a potted plant.

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

11. Howard Hotel

Hudson

Loretta

฿4,039

฿4,564 total

includes taxes & fees

9 Sept - 10 Sept

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A motel with a parking lot and several cars parked.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

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

12. Monument Mountain Motel

Great Barrington

John

฿2,811

฿3,139 total

includes taxes & fees

1 Sept - 2 Sept

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

13. Wilder House Berkshires

Sheffield

Jennifer

฿6,467

฿7,224 total

includes taxes & fees

1 Sept - 2 Sept

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

14. Granville House

Housatonic

Nicole

฿9,019

฿10,075 total

includes taxes & fees

10 Sept - 11 Sept

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

15. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Elspeth

฿2,597

฿2,901 total

includes taxes & fees

1 Sept - 2 Sept

A red building with a sign reading "Shaker Mill Inn."

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

16. Shaker Mill Inn

West Stockbridge

Mervin

฿5,786

฿6,347 total

includes taxes & fees

9 Sept - 10 Sept

17. Berkshire Travel Lodge

Austerlitz

Kris

฿2,214

฿2,479 total

includes taxes & fees

22 Sept - 23 Sept

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

18. Quality Inn Lee - Lenox South

Lee

Christine

฿3,605

฿4,026 total

includes taxes & fees

17 Sept - 18 Sept

A residential garden with a pathway leading to a house.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and flowers.

A residential property with a swimming pool, a covered patio area, and a well-maintained lawn.

A circular outdoor fire pit with a metal rim, surrounded by gravel.

19. The Amelia

Hudson

Kylene

฿12,012

฿13,574 total

includes taxes & fees

7 Sept - 8 Sept

A large house with a balcony and a grassy yard.

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

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

20. The Little Lion

Great Barrington

Anne

฿3,690

฿4,121 total

includes taxes & fees

1 Sept - 2 Sept

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Top Craryville Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"It is a safe place with friendly staff and clean accommodations; it is an excellent spot for traveling with children."

Quality Inn Lee - Lenox South

10/10 Excellent

"Friendly staff and clean comfortable room! Location is super"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."

St. Charles Hotel

8/10 Good

"Place was clean. Bed was comfortable. Air conditioning was very loud!!"

The Red Lion Inn

10/10 Excellent

"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."

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."

Howard Johnson by Wyndham Saugerties

8/10 Good

"good facility"

Residence Inn by Marriott Kingston

10/10 Excellent

"Amazing location and property. One of the best hotels we stayed in"

Mirbeau Inn & Spa

10/10 Excellent

"Terrific stay"

More cheap stays in Craryville