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Ashland Hotels with Swimming Pool

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Check availability on Ashland Hotels with Swimming Pools

Tonight
28 Sept - 29 Sept
Tomorrow
29 Sept - 30 Sept
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 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.
A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
RM473
RM581 total
includes taxes & fees
1 Oct - 2 Oct
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 building with a large front porch, a chimney, and a balcony.
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.
RM489
RM528 total
includes taxes & fees
29 Sept - 30 Sept
Moore's Motel
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 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".

3. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
RM363
RM399 total
includes taxes & fees
29 Sept - 30 Sept
The Colonial 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 compact living space with a kitchen, dining area, and seating.
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

4. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
RM608
RM657 total
includes taxes & fees
29 Sept - 30 Sept
The Winwood Condominiums
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 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.

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.
RM803
RM957 total
includes taxes & fees
27 Oct - 28 Oct
Kaatskill Mountain Club & Condos by Vail Resorts
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.
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.

6. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
RM1,091
RM1,382 total
includes taxes & fees
29 Oct - 30 Oct
Wylder Hotel Windham
A swimming pool with clear blue water, surrounded by trees and equipped with lounge chairs.
A compact kitchen with a central island, a microwave, a stove, a refrigerator, and a cabinet with glass doors.
A kitchen with a wooden shelf holding mugs and a toaster oven.
A cozy room with a fireplace, a wooden table with books and glasses, and a blue sofa.

7. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Serene seasonal pool oasis nestled in the Catskill Mountains offers perfect summer refreshment.
RM652
RM730 total
includes taxes & fees
29 Sept - 30 Sept
Catskill Seasons Inn
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 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.

8. 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.
RM695
RM778 total
includes taxes & fees
29 Sept - 30 Sept
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Very nice property with very nice rooms and great staff. Would definitely recommend!"
Paul 1-night trip
Posted 3 days ago
Hotel Vienna

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. Features 2 hot tubs, an outdoor pool and a sauna. Kaatskill Mountain Club & Condos by Vail Resorts: Features a snack bar/deli, a seasonal outdoor pool and on-the-go. Urban Cowboy Lodge: 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 18Β°C, while the coldest months are January and February, with an average of -3Β°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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