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Ashland Hotel Guide - Hotels with Pool in Ashland, New York

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Check availability on Ashland Hotels with Pool

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Ashland hotels with a pool

A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.
A log cabin with a deck, outdoor seating, and a view of a forest.
A cabin with a deck, large windows, and a mountain backdrop.
A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
€127
includes taxes & fees
10 Nov - 11 Nov
Hotel Vienna
A swimming pool with lounge chairs and potted plants.
A two-story motel with a central staircase, balconies, and a grassy front yard.
A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.
A two-story building with a large front porch, a chimney, and a balcony.

2. Moore's Motel

Moore's Motel
Prattsville
  • Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
€116
includes taxes & fees
18 Oct - 19 Oct
Moore's Motel
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
A compact living space with a kitchen, dining area, and seating.
A two-story building with a balcony, surrounded by well-maintained lawns and trees.
A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
€163
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
A covered porch with outdoor seating, a staircase, and potted plants.

4. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
€88
includes taxes & fees
20 Oct - 21 Oct
The Colonial Motel
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
A modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.

5. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
€230
includes taxes & fees
29 Oct - 30 Oct
Wylder Hotel Windham
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
A multi-story building with outdoor seating and a stone-paved patio.
A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.
A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

6. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
  • Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
€191
includes taxes & fees
15 Nov - 16 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
An indoor swimming pool area with a hot tub, seating, and a caution sign.
A modern building with large windows, a covered outdoor area with seating, and a pool.
A spacious living area with a wooden staircase, a kitchen in the background, and a large window providing a view of the outdoors.
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

7. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
€444
includes taxes & fees
3 Nov - 4 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.
A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

8. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
€142
includes taxes & fees
27 Oct - 28 Oct
Shandaken Inn
A log cabin with a porch, a staircase, and a garage.
A bathroom with a white sink, a shower curtain, and a tiled wall.
A kitchen with dark green cabinets, a tiled backsplash, a stainless steel sink, and a decorative Buddha head.
A living room with a flat-screen TV on a wooden stand, a fireplace, a clock, and two framed artworks on the wall.

9. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
€204
includes taxes & fees
18 Oct - 19 Oct
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A log cabin with a tower, a swimming pool, and lounge chairs.
A spacious dining area with wooden beams, large windows, and a central island with tables and chairs.
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.
A couple standing on a wooden deck overlooking a landscaped garden with a river view.

10. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Seasonal outdoor pool beckons with shady umbrellas in the heart of Catskill Mountains.
€179
includes taxes & fees
15 Nov - 16 Nov
Emerson Resort & Spa
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Choose what matters most at hotels with a pool in Ashland

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Ashland Hotel Reviews

The Graham & Co.

The Graham & Co.

10/10 Excellent
"I had a pleasant stay! The place was nice and comfortable, and everything was good. Thank you for your hospitality. I would definitely recommend it!"
Emir 1-night trip
Posted 18 hours ago
The Graham & Co.

Frequently asked questions

What are some hotels with pools in Ashland?
Hunter Lodge, a Bluebird by Lark: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli. Emerson Resort & Spa: Hotel located near Windham Mountain Resort. Provides daily, an indoor pool and free self parking. Hotel Vienna: Hotel, 1-minute walk from Hunter Mountain. Offers 2 hot tubs, an outdoor pool and a sauna. Urban Cowboy Lodge: Features a snack bar/deli, a seasonal outdoor pool and on-the-go. Kaatskill Mountain Club & Condos by Vail Resorts: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool and complimentary bicycles.
What is there to see and do in Ashland?
The picturesque settings of Mountain Top Arboretum and Belleayre Beach showcase the area's natural beauty. Discover sights such as Ashland Town Hall during your stay.
When is the best time to book a hotel with a pool in Ashland?
Taking the local weather in Ashland into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Ashland are January, March, December and November, with each month seeing an average of 18 cm of snowfall.