Ashland Holiday Rentals, New York: Private House Rentals

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Our top choices for Ashland hotels

A log cabin with a deck, outdoor seating, and a view of a forest.

A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

A cozy cabin interior with a stone fireplace, wooden walls, a dining area with a red and black checkered tablecloth, and a television mounted above the fireplace.

A wooden covered bridge in a forested area with a paved path leading to it.

1. Hotel Vienna

Windham

john

Rp2.068.670

Rp2.542.057 total

includes taxes & fees

1 Oct - 2 Oct

A swimming pool with lounge chairs and potted plants.

A hotel room with two beds, a desk, a chair, and a TV on a stand.

A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.

A two-story motel with a central staircase, balconies, and a grassy front yard.

2. Moore's Motel

Prattsville

Cory

Rp2.138.160

Rp2.309.213 total

includes taxes & fees

25 Sept - 26 Sept

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

A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.

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

A cozy lounge area with a sofa, armchairs, a coffee table, and a bookshelf.

3. Hunter Lodge, a Bluebird by Lark

Hunter

Shubhangi

Rp2.408.103

Rp2.985.620 total

includes taxes & fees

25 Oct - 26 Oct

A covered porch with outdoor seating, a staircase, and potted plants.

A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

A cozy room with a white sofa, a wooden table with a lamp, and a chair with a patterned cushion. There's a reception desk with a computer and a sign that says "Welcome".

A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

4. The Colonial Motel

Grand Gorge

Eric

Rp1.587.584

Rp1.746.164 total

includes taxes & fees

27 Sept - 28 Sept

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

A bathroom with three sinks, a trash can, and a chair.

A large tree in a grassy area with a small white building in the background.

A park with picnic tables and chairs, a tall cylindrical structure, and autumn-colored trees.

5. SunView Motel

Tannersville

Victoria

Rp1.857.527

Rp2.006.129 total

includes taxes & fees

1 Oct - 2 Oct

A two-story building with a balcony, surrounded by well-maintained lawns and trees.

A compact living space with a kitchen, dining area, and seating.

A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

6. The Winwood Condominiums

Windham

Abdul

Rp2.659.337

Rp2.872.083 total

includes taxes & fees

27 Sept - 28 Sept

A multi-story building with outdoor seating and a stone-paved patio.

A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

7. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Nuria

Rp3.521.193

Rp4.192.932 total

includes taxes & fees

28 Sept - 29 Sept

A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

A pool table with balls and a cue stick.

A wooden room with a bed, a nightstand with a lamp, and a wall with tree decorations.

8. Jimmy OConnors Windham Mountain Inn

Windham

James

Rp2.645.973

Rp2.857.651 total

includes taxes & fees

27 Sept - 28 Sept

A large, two-story house with multiple porches and string lights.

A building with a porch and outdoor seating area.

A grassy field with a wooden structure overhead, possibly a gazebo or pavilion.

A room with a wooden floor, a chair, a lamp, and a view through a window with a decorative frame.

9. Albergo Allegria Hotel

Windham

Roy

Rp3.095.878

Rp3.343.548 total

includes taxes & fees

27 Sept - 28 Sept

A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

A covered outdoor seating area with wicker chairs and a table, surrounded by white railings and hanging planters.

A garden with blooming pink flowers and green grass.

A wooden staircase leading to a second floor, a red sofa with floral cushions, and a wooden floor.

10. Antique Rose Inn Windham

Windham

David

Rp2.405.430

Rp2.597.864 total

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

A reception desk with a mirror, potted plants, a welcome sign, and a bench with patterned cushions.

A person walking towards a yellow door with stone walls and a bench to the left.

A covered outdoor seating area with picnic tables and umbrellas, surrounded by a forest.

11. Starlite Motel

Big Indian

Sarah

Rp2.227.250

Rp2.494.520 total

includes taxes & fees

28 Sept - 29 Sept

A wooden cabin with a triangular roof, a wooden door, and a bench outside.

A wooden cabin with a balcony, surrounded by snow-covered trees.

A round wooden table with a hanging light fixture, surrounded by four stools, set against a backdrop of a large window with a view of trees and a wooden deck.

A triangular wooden room with a bed and pillows, a window, and a view of a forested hill.

12. Eastwind Windham

Windham

Sharon

Rp4.218.055

Rp5.088.108 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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 bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.

13. Hotel Mountain Brook

Tannersville

Kristen

Rp3.634.872

Rp3.925.662 total

includes taxes & fees

30 Sept - 1 Oct

14. The Wheelhouse Inn

Pine Hill

Allen

Rp3.029.060

Rp3.392.547 total

includes taxes & fees

26 Sept - 27 Sept

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

A cozy living room with a fireplace, two sofas, a coffee table, and a dining area with chairs and a table.

An aerial view of a motel with a long, single-story building, a parking lot, and a road in the foreground.

A wooden desk with a brochure, a lamp, and a mirror reflecting a bed and a ceiling fan.

15. Margaretville Motel

Margaretville

Dianna

Rp1.514.530

Rp1.951.071 total

includes taxes & fees

27 Sept - 28 Sept

A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

A hotel room with a bed, white curtains, and wall-mounted light fixtures.

A room with a curved wooden ceiling, large windows with wooden frames, two upholstered armchairs, a round table, and a potted plant.

A bathroom with a blue-tiled shower enclosure, a shelf with toiletries, and a handheld showerhead.

16. Shadowcrest

Fleischmanns

Margo

Rp2.351.976

Rp2.587.174 total

includes taxes & fees

27 Sept - 28 Sept

A river flowing through a forested area with rocks and autumn-colored trees.

A front door with a WiFi sign, a Christmas wreath, and a bear statue.

A wooden sign for Black Bear Lodge with a phone number.

Two white Adirondack chairs in a forest with fallen leaves.

17. Black Bear Lodge

Prattsville

Gerald

Rp2.654.882

Rp2.867.273 total

includes taxes & fees

27 Sept - 28 Sept

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.

18. Wylder Hotel Windham

Windham

Yousung

Rp4.590.859

Rp5.849.027 total

includes taxes & fees

27 Sept - 28 Sept

A dining area with a stone fireplace, wooden beams, and large windows.

A spacious living room with a stone fireplace, wooden beams, and large windows.

A row of red buildings with a gravel driveway and a bench outside.

19. Phoenicia Lodge

Phoenicia

Thomas

Rp3.082.870

Rp3.452.772 total

includes taxes & fees

28 Sept - 29 Sept

A park with Adirondack chairs and a table, surrounded by trees.

A dining table set with breakfast items, a red mug, and a glass of orange juice.

A lamp post in a grassy area with autumn foliage in the background.

A vintage car parked in front of a house surrounded by trees.

20. Mountain Treasure B&B

Maplecrest

Daniel

Rp2.957.788

Rp3.194.411 total

includes taxes & fees

18 Oct - 19 Oct

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Top Ashland Hotel Reviews

Urban Cowboy Lodge

10/10 Excellent

"A fabulous establishment, lots to do on site!"

The Colonial Motel

10/10 Excellent

"Absolutely wonderful place to stay"

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"I love how rustic the decor is, the dog friendly policy was my ultimate favorite. My puppy, boyfriend and I had a marvelous time and stay. The staff was wonderful helped me with trails, the restaurant food was delightful and so was the bar. Will be coming back!!"

Jimmy OConnors Windham Mountain Inn

10/10 Excellent

"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."

Emerson Resort & Spa

10/10 Excellent

"If you are looking for a very peaceful, serene getaway to completely reset, book this place immediately. The quiet, beautiful atmosphere makes it a true sanctuary.The hospitality here is next level. Jackie was incredibly nice and welcoming from start to finish. Jonathan went out of his way to take gorgeous birthday pictures for me the second I asked. The absolute hero of my trip was Kristine, who literally saved me when I found myself stranded in the middle of nowhere!This team protects your peace of mind, I am telling everyone about this gem, and I am definitely coming back to the Emerson!"

SunView Motel

8/10 Good

"Quiet and comfortable! We would definitely stay here again."

Shandaken Inn

8/10 Good

"The hotel staff is very friendly and provides excellent service . The room is clean and comfortable. The breakfast is not really good. The potatoes are too spicy. We asked the waitress if we could change. She rejected directly and didn’t give us any choices. However, when we had the breakfast in second day morning, we required to change too spicy potatoes. The waitress was very nice and helped change to fruit after she talked with supervisor. If the breakfast could give more choices, the hotel would be more attractive."

Starlite Motel

10/10 Excellent

"Great place to get away for the weekend. Spent our first wedding anniversary here and couldn’t have been happier."

The Graham & Co.

8/10 Good

"The owners and staff are very friendly. Relaxing atmosphere. We stayed in the deluxe double room. The oven and refrigerator in the room could use some attention and cleaning. Bathroom well stocked but shower was basic. Could use a little refurbishing."