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Hotels with Swimming Pools in Ashland

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Check availability on Ashland Hotels with Swimming Pools

Tonight
31 Aug - 1 Sept
Tomorrow
1 Sept - 2 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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 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.
A cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
S$181
includes taxes & fees
14 Sept - 15 Sept
Hotel Vienna
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A covered porch with outdoor seating, a staircase, and potted plants.
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.

2. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
S$121
includes taxes & fees
7 Sept - 8 Sept
The Colonial Motel
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 hotel room with two beds, a desk, a chair, and a TV on a stand.

3. 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$165
includes taxes & fees
1 Sept - 2 Sept
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 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.

4. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
S$246
includes taxes & fees
1 Sept - 2 Sept
The Winwood Condominiums
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 cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.

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.
S$285
includes taxes & fees
30 Sept - 1 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 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.
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.
S$416
includes taxes & fees
2 Sept - 3 Sept
Wylder Hotel Windham
A two-story building with a dark exterior, surrounded by a grassy area with picnic tables.
A room with a bed, a wooden dining table, chairs, a chandelier, a fireplace, and a television.
A modern bathroom with a freestanding bathtub, a towel rack, and a wooden cabinet.
A hotel room with two beds, a nightstand, a lamp, and a window with blinds.

7. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Serene seasonal pool oasis nestled in the Catskill Mountains offers perfect summer refreshment.
S$228
includes taxes & fees
1 Sept - 2 Sept
Catskill Seasons Inn
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 stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.

8. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
S$289
includes taxes & fees
1 Oct - 2 Oct
Shandaken Inn
A pool area with a wooden deck, benches, and umbrellas.
A corridor with white walls, wooden slats, and a concrete floor.
A campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.
A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.

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$230
includes taxes & fees
8 Sept - 9 Sept
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"We really enjoyed the experience."
David 2-night trip
Posted 9 hours ago
Hotel Vienna
The Graham & Co.

The Graham & Co.

10/10 Excellent
"Wonderful Stay"
Daniel 2-night trip
Posted 6 days ago
The Graham & Co.

Frequently asked questions

What are some hotels with pools in Ashland?
Hunter Lodge, a Bluebird by Lark: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool and complimentary bicycles. Wylder Hotel Windham: Provides a full-service spa, a seasonal outdoor pool and complimentary bicycles. Emerson Resort & Spa: Hotel, 1-minute walk from Hunter Mountain. Features 2 hot tubs, an outdoor pool and a sauna. Kaatskill Mountain Club & Condos by Vail Resorts: Hotel located near Windham Mountain Resort. Features daily, an indoor pool and free self parking. Urban Cowboy Lodge: Offers a snack bar/deli, a seasonal outdoor pool and on-the-go.
What is there to see and do in Ashland?
The picturesque settings of Belleayre Beach and East Branch Delaware River 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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