Shady Holiday Rentals, Bearsville: Private House Rentals

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Our top choices for Shady hotels

A wooden deck with outdoor seating, a wooden deck with a view of the interior, and a wooden deck with a view of the exterior.

A modern living room with a grey sofa, a small round table, and a hanging light fixture.

A modern bedroom with a wooden bed, a desk, and large windows.

A two-story wooden house with a stone retaining wall, a stone pathway, and a small garden with various plants.

1. Woodstock Way Hotel

Woodstock

Vannetta

฿11,033

฿13,673 total

includes taxes & fees

2 Nov - 3 Nov

A living room with a fireplace, green sofa, and a leopard print armchair.

A hallway with a patterned floor, a potted plant, a chandelier, and a door with a decorative mirror.

A wooden deck with outdoor seating and a house in the background.

A modern bedroom with a large bed, a bedside table with a lamp, a view of greenery outside, and a checkered rug.

2. Twin Gables of Woodstock

Woodstock

Barbara

฿5,200

฿5,824 total

includes taxes & fees

9 Nov - 10 Nov

A white house with a porch, surrounded by lush greenery and two green Adirondack chairs.

A bedroom with a large bed, a fireplace, a TV, and a painting on the wall.

A picnic setup with a table, food, drinks, and binoculars by a stream.

A cozy living room with a fireplace, comfortable seating, and a dining area with a table set for four.

3. The Woodstock Inn on the Millstream

Woodstock

Carolyn

฿7,732

฿8,660 total

includes taxes & fees

27 Oct - 28 Oct

A hotel with a covered entrance, stone facade, and a sign indicating it is a Holiday Inn Express & Suites.

A hotel lobby with a reception desk, seating area, and a refrigerator stocked with beverages.

A buffet with various food items, including omelets and baked goods, served in metal containers.

A row of refrigerators with shelves stocked with beverages and condiments.

4. Holiday Inn Express & Suites Kingston-Ulster by IHG

Lake Katrine

Timothy

฿4,389

฿4,916 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with a fire pit, seating, and a building in the background.

A modern cafe with a wooden counter, bar stools, and a menu board above the counter.

A modern hotel room with a grey sofa, an orange armchair, a small wooden table, and a large window with sheer curtains.

A hotel room with two beds, a desk, a chair, and a large window with curtains.

5. Courtyard by Marriott Kingston

Kingston

Yvette

฿3,989

฿4,468 total

includes taxes & fees

1 Nov - 2 Nov

A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.

A spacious living area with a sofa, armchairs, and a coffee table. There is a dining area with chairs and a table, and a stone fireplace.

A Hampton Inn hotel with a modern facade, multiple entry points, and a well-lit entrance.

An indoor swimming pool with clear water, a 5 feet deep sign, and a tiled floor.

6. Hampton Inn Kingston

Kingston

Jennifer

฿4,125

฿4,620 total

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a fireplace, comfortable seating, and large windows.

A multi-story hotel with a well-lit entrance, a flag, and a sign indicating it is a Marriott Residence Inn.

An outdoor patio with a fire pit, wicker furniture, and a red building in the background.

A breakfast buffet setup with a variety of food items, including bread, cereal, and fruits, in a modern hotel dining area with striped chairs and a large window.

7. Residence Inn by Marriott Kingston

Kingston

Kathy Reilly

฿4,524

฿5,067 total

includes taxes & fees

1 Nov - 2 Nov

A lodge with a registration area, a covered porch, and a pond with a bridge.

A well-maintained garden with a red bridge, a welcome sign, and a building with a gabled roof.

A couple standing on a wooden deck overlooking a landscaped garden with a river view.

A hallway with intricate carvings on the walls and a large vase in the center.

8. Emerson Resort & Spa

Mount Tremper

Jeremy

฿6,044

฿6,769 total

includes taxes & fees

1 Nov - 2 Nov

A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.

A modern house with a sloped roof, large windows, and a well-maintained lawn.

A modern house with a large garage and a vintage camper parked in the driveway.

A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.

9. AutoCamp Catskills

Saugerties

Raquel

฿4,714

฿6,604 total

includes taxes & fees

4 Nov - 5 Nov

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

A modern hotel lobby with a wooden floor, a reception desk, two patterned armchairs, a chandelier, and a view of the outdoors through a glass door.

A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

A wooden-paneled bedroom with a bed, bedside tables, and a hanging light fixture.

10. Hotel Mountain Brook

Tannersville

Kim

฿8,238

฿8,897 total

includes taxes & fees

17 Nov - 18 Nov

An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

A Howard Johnson Inn with a beige facade, red trim, and a clear blue sky with clouds.

A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.

A hotel room with two beds, a TV, a dresser, and a door leading to another room.

11. Howard Johnson by Wyndham Saugerties

Saugerties

Shirley

฿3,707

฿4,152 total

includes taxes & fees

2 Nov - 3 Nov

A wooden table with a bottle of wine, two glasses, and a lit fire pit.

A bedroom with a large window offering a view of a forested mountain.

A modern living room with a large window, a blue sofa, a wooden coffee table, and a rustic wooden wall.

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

12. Hunter Lodge, a Bluebird by Lark

Hunter

Marina

฿3,989

฿5,038 total

includes taxes & fees

8 Nov - 9 Nov

A serene garden with a stone pathway, a small bridge, and a bench.

A hallway with a framed portrait on the wall, a door to the right, and a window on the left.

A room with a large tapestry, two wicker chairs, a small table, and a globe lamp.

A dining area with a wooden table, chairs, a chandelier, and a view of the outdoors through large windows.

13. Morning Glory B n B Woodstock NY

Woodstock

Lucian

฿7,394

฿8,282 total

includes taxes & fees

2 Nov - 3 Nov

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

A Holiday Inn Express & Suites sign with a clear view of the hotel building in the background.

A modern lobby with a reception desk, seating area, and a dining section.

A modern breakfast area with a coffee machine, cereal, and bakery options.

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

Saugerties

Jacqueline

฿4,119

฿4,614 total

includes taxes & fees

8 Nov - 9 Nov

A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.

A historic hotel with a prominent tower and a brick facade.

A bar with a patterned floor, bar stools, and a bar counter with taps.

15. Diamond Mills Resort

Saugerties

luping

฿8,974

฿10,895 total

includes taxes & fees

27 Oct - 28 Oct

An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.

A buffet area with various food items, a coffee machine, and a refrigerator.

A hotel room with a bed, a desk, a sofa, and two lamps.

A hotel room with a bed, desk, chair, TV, and kitchenette.

16. Comfort Inn Saugerties

Saugerties

Tevfik

฿4,832

฿5,411 total

includes taxes & fees

1 Nov - 2 Nov

A cozy living room with a wood-burning stove, wicker furniture, and a bookshelf.

A restaurant with orange seating, white tablecloths, and potted plants.

A room with a red accent wall, a large potted plant, and a small stool.

A living room with a red patterned rug, a blue armchair, a yellow sofa, and a black coffee table.

17. Hotel Kinsley

Stockade District

David

฿8,007

฿10,427 total

includes taxes & fees

24 Nov - 25 Nov

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

A multi-story hotel with a flat roof, large windows, and a brick facade.

A hotel lobby with a reception desk, two armchairs, a small table, and a lamp.

A bathroom with a walk-in shower, grab bars, and a white tiled wall.

18. Super 8 by Wyndham Kingston

Kingston

David

฿2,841

฿3,182 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with a glass ceiling, indoor seating, and a brick wall.

A restaurant with booths, tables, and a bar area.

A hotel room with a sofa, ottoman, desk, chair, television, and a mirror.

A hotel room with two beds, a desk, and a large window.

19. Kingston Regency Inn

Kingston

Colleen

฿4,221

฿5,186 total

includes taxes & fees

12 Nov - 13 Nov

A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

A pool area with a wooden deck, benches, and umbrellas.

A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.

A corridor with white walls, wooden slats, and a concrete floor.

20. The Graham & Co.

Phoenicia

Cindy

฿5,274

฿5,907 total

includes taxes & fees

2 Nov - 3 Nov

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Top Shady Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent

"Nice weekend stay. The hotel had everything that we needed."

Super 8 by Wyndham Kingston

8/10 Good

"Great location, clean just outdated and thin walls."

Howard Johnson by Wyndham Saugerties

10/10 Excellent

"No complaints"

Hotel Vienna

10/10 Excellent

"Very clean and cozy. Close to many attractions. The staff was friendly, would recommend."

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

10/10 Excellent

"Excellent hotel all around. Pleasant and accomodating staff - everyone we dealt with was professional, helpful and polite. The hotel is recently updated and very clean - lobby, hallways, staircases, bathrooms, our room. It was actually THE cleanest hotel we ever stayed at. Breakfast very nice, 2 protein choices, fresh fruit, etc. Location is great too - close to everything. Definetly recommend."

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"Good getaway from the city"

Courtyard by Marriott Kingston

8/10 Good

"Hotel was as expected. No complaints. Staff was friendly. Location is OK if you're passing through. It's not in town but in a large parking lot/retail area, with a few chain restaurants and stores like Target nearby. It took about a 10 minute drive to get to a local restaurant."

Kingston Regency Inn

8/10 Good

"Good stay for the price."

Hotel Kinsley

8/10 Good

"The breakfast could have been better."