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Hotels with Swimming Pools in Ashland

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Check availability on Ashland Hotels with Swimming Pools

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 cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.
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.
S$183
includes taxes & fees
8 Nov - 9 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 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.

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.
S$166
includes taxes & fees
19 Oct - 20 Oct
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 compact living space with a kitchen, dining area, and seating.
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
S$234
includes taxes & fees
1 Nov - 2 Nov
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 restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.

4. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
S$330
includes taxes & fees
29 Oct - 30 Oct
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 covered porch with outdoor seating, a staircase, and potted plants.
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.
S$106
includes taxes & fees
15 Nov - 16 Nov
The Colonial Motel
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 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.

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.
S$269
includes taxes & fees
15 Nov - 16 Nov
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 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.

7. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
S$204
includes taxes & fees
8 Nov - 9 Nov
Shandaken Inn
A log cabin with a tower, a swimming pool, and lounge chairs.
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.
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.

8. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Seasonal outdoor pool beckons with shady umbrellas in the heart of Catskill Mountains.
S$236
includes taxes & fees
8 Nov - 9 Nov
Emerson Resort & Spa
A pool area with a wooden deck, benches, and umbrellas.
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.
A corridor with white walls, wooden slats, and a concrete floor.

9. 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.
S$224
includes taxes & fees
11 Nov - 12 Nov
The Graham & Co.
A swimming pool with lounge chairs and a building in the background.
A kitchen with a stove, kettle, toaster, and utensils on the counter.
A hotel room with two single beds, a nightstand with a lamp, and a dark blue accent wall.
A bathroom with a toilet, a bathtub, and a shower.

10. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Serene seasonal pool oasis nestled in the Catskill Mountains offers perfect summer refreshment.
S$249
includes taxes & fees
19 Oct - 20 Oct
Catskill Seasons Inn
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Clean room and helpful staff, good location."
Hongtao 1-night trip
Posted less than an hour ago
Hotel Vienna
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 19 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.

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