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Find Hotels with a Pool in Ashland, NY

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Check availability on Ashland Hotels with a Pool

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

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 cabin with a deck, large windows, and a mountain backdrop.
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.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
NT$3,734
NT$4,588 total
includes taxes & fees
Nov 8 - Nov 9
Hotel Vienna
A swimming pool with lounge chairs and potted plants.
A two-story building with a large front porch, a chimney, and a balcony.
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

Moore's Motel
Prattsville
  • Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
NT$3,859
NT$4,168 total
includes taxes & fees
Oct 19 - Oct 20
Moore's Motel
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
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.
A compact living space with a kitchen, dining area, and seating.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
NT$5,435
NT$5,870 total
includes taxes & fees
Nov 2 - Nov 3
The Winwood Condominiums
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.

4. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
NT$6,152
NT$8,253 total
includes taxes & fees
Oct 29 - Oct 30
Wylder Hotel Windham
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
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".

5. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
NT$2,866
NT$3,152 total
includes taxes & fees
Oct 19 - Oct 20
The Colonial Motel
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 lounge area with leather sofas, a fireplace, and a large window overlooking a garden.
A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

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.
NT$5,776
NT$6,878 total
includes taxes & fees
Nov 15 - Nov 16
Kaatskill Mountain Club & Condos by Vail Resorts
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
A stone building with a chimney, a pool, and a sign for Shandaken Inn.
A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.
A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.

7. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
NT$4,573
NT$5,122 total
includes taxes & fees
Nov 12 - Nov 13
Shandaken Inn
A log cabin with a tower, a swimming pool, and lounge chairs.
A hallway with intricate carvings on the walls and a large vase in the center.
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.

8. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Seasonal outdoor pool beckons with shady umbrellas in the heart of Catskill Mountains.
NT$5,757
NT$6,448 total
includes taxes & fees
Nov 8 - Nov 9
Emerson Resort & Spa
A swimming pool with lounge chairs and umbrellas.
A cozy living room with a plaid sofa, a fireplace, and various decorative items on shelves above the fireplace.
A buffet table with various food items and a painting on the wall.
A wooden lodge with a welcoming sign, a bear statue, and two flags.

9. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
NT$7,013
NT$7,574 total
includes taxes & fees
Oct 30 - Oct 31
Crystal Brook Resort & Mountain Brauhaus
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 campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.
A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

10. The Graham & Co.

The Graham & Co.
Phoenicia
  • Splash into poolside fun at this Catskill Mountains motel, where seasonal swimming meets adventure in a charming outdoor oasis.
NT$5,024
NT$5,627 total
includes taxes & fees
Nov 12 - Nov 13
The Graham & Co.
View all properties

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 setting 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 into account the local weather in Ashland is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Ashland are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

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