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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
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Ashland hotels with a pool

Indoor pool
View from room
Exterior
Exterior

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
NT$3,699
NT$4,545 total
includes taxes & fees
Aug 27 - Aug 28
Hotel Vienna
Outdoor pool
Meeting facility
Room, 2 Double Beds | WiFi (free)
Porch

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$3,823
NT$4,129 total
includes taxes & fees
Aug 25 - Aug 26
Moore's Motel
Seasonal outdoor pool, pool umbrellas, sun loungers
Exterior
Property entrance
Exterior

3. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
NT$2,839
NT$3,123 total
includes taxes & fees
Aug 25 - Aug 26
The Colonial Motel
Seasonal outdoor pool
Living area
Exterior
Living area

4. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
NT$5,306
NT$5,731 total
includes taxes & fees
Aug 25 - Aug 26
The Winwood Condominiums
Outdoor pool
Exterior
Exterior
32-inch TV with cable channels

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.
NT$5,853
NT$6,970 total
includes taxes & fees
Aug 26 - Aug 27
Kaatskill Mountain Club & Condos by Vail Resorts
Outdoor pool
Exterior
Restaurant
Hair dryer, bathrobes, towels

6. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
NT$6,952
NT$9,101 total
includes taxes & fees
Aug 26 - Aug 27
Wylder Hotel Windham
Seasonal outdoor pool
Exterior
Apartment, 3 Bedrooms | Living area | 30-inch flat-screen TV with cable channels, TV
Exterior

7. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Serene seasonal pool oasis nestled in the Catskill Mountains offers perfect summer refreshment.
NT$5,097
NT$5,709 total
includes taxes & fees
Aug 25 - Aug 26
Catskill Seasons Inn
Terrace/patio
Fireplace
Property grounds
Front of property - evening/night

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.
NT$5,127
NT$5,743 total
includes taxes & fees
Sep 8 - Sep 9
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

Catskill Seasons Inn

Catskill Seasons Inn

10/10 Excellent
"Easy self check-in, clean room, nice pool, nice fire pit, plenty of parking."
Christian 2-night trip
Posted 20 hours ago
Catskill Seasons Inn
The Graham & Co.

The Graham & Co.

10/10 Excellent
"This recently renovated hotel is delightfully retro chic. Comfortable, clean, and well run. Three fire pits make for fun evenings with children eating s'mores. Coffee ready every morning (with real milk and cream) in the reception area and continental breakfasts delivered to your door on weekends. Lovely pool area. Short walk to downtown Phoenicia shops and restaurants. We enjoyed our stay!"
Linda 4-night trip
Posted 2 days ago
The Graham & Co.

Frequently asked questions

What are some hotels with pools in Ashland?
Hunter Lodge, a Bluebird by Lark: 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: 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 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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