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Hotels with Swimming Pool in Ashland, New York

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Check availability on Ashland Hotels with Swimming 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 cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.
A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.
A cabin with a deck, large windows, and a mountain backdrop.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
P7,291
P8,959 total
includes taxes & fees
Nov 8 - Nov 9
Hotel Vienna
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 two-story motel with a central staircase, balconies, and a grassy front yard.
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.
P7,536
P8,139 total
includes taxes & fees
Oct 16 - Oct 17
Moore's Motel
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.
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 two-story building with a balcony, surrounded by well-maintained lawns and trees.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
P10,628
P11,478 total
includes taxes & fees
Nov 1 - Nov 2
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 modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

4. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
P12,010
P16,111 total
includes taxes & fees
Oct 29 - Oct 30
Wylder Hotel Windham
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
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 building with outdoor seating and a stone-paved patio.

5. 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.
P11,291
P13,445 total
includes taxes & fees
Nov 15 - Nov 16
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
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 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.

6. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
P5,595
P6,154 total
includes taxes & fees
Oct 20 - Oct 21
The Colonial Motel
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.
A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

7. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
P8,942
P10,016 total
includes taxes & fees
Oct 27 - Oct 28
Shandaken Inn
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 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

Emerson Resort & Spa
Mount Tremper
  • Seasonal outdoor pool beckons with shady umbrellas in the heart of Catskill Mountains.
P11,256
P12,607 total
includes taxes & fees
Nov 1 - Nov 2
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 sign for Crystal Brook Resort surrounded by red tulips.
A buffet table with various food items and a painting on the wall.

9. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
P13,690
P14,785 total
includes taxes & fees
Oct 30 - Oct 31
Crystal Brook Resort & Mountain Brauhaus
A pool area with a wooden deck, benches, and umbrellas.
A corridor with white walls, wooden slats, and a concrete floor.
A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.
A campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.

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.
P9,809
P10,987 total
includes taxes & fees
Nov 2 - Nov 3
The Graham & Co.
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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 17 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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