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Search Hotels with Swimming Pool in Ashland

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Check availability on Ashland Hotels with Swimming Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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.

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (898 reviews)
  • cleanliness
    Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
The price is ₹10,701
₹13,201 total
includes taxes & fees
2 Nov - 3 Nov
Hotel Vienna
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

2. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (134 reviews)
  • cleanliness
    Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
The price is ₹13,612
₹19,456 total
includes taxes & fees
31 Oct - 1 Nov
Wylder Hotel Windham
A swimming pool with lounge chairs and potted plants.

3. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (183 reviews)
  • cleanliness
    Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
The price is ₹11,414
₹12,327 total
includes taxes & fees
30 Oct - 31 Oct
Moore's Motel
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

4. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (372 reviews)
  • cleanliness
    Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
The price is ₹16,075
₹17,361 total
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

5. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (443 reviews)
  • cleanliness
    Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
The price is ₹16,180
₹19,267 total
includes taxes & fees
22 Nov - 23 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with a fenced deck, lounge chairs, and umbrellas.

6. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (501 reviews)
  • cleanliness
    Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
The price is ₹7,628
₹8,390 total
includes taxes & fees
3 Nov - 4 Nov
The Colonial Motel
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.

7. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (331 reviews)
  • cleanliness
    Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
The price is ₹13,536
₹15,161 total
includes taxes & fees
2 Nov - 3 Nov
Shandaken Inn
A log cabin with a tower, a swimming pool, and lounge chairs.

8. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.2 out of 10, Wonderful, (110 reviews)
  • cleanliness
    Seasonal outdoor pool beckons with shady umbrellas in the heart of Catskill Mountains.
The price is ₹15,040
₹16,845 total
includes taxes & fees
29 Oct - 30 Oct
Emerson Resort & Spa
A swimming pool with lounge chairs and umbrellas.

9. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
2.5 star property
Round Top
9.0 out of 10, Wonderful, (102 reviews)
The price is ₹20,736
₹22,395 total
includes taxes & fees
30 Oct - 31 Oct
Crystal Brook Resort & Mountain Brauhaus
A pool area with a wooden deck, benches, and umbrellas.

10. The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.6 out of 10, Exceptional, (67 reviews)
  • cleanliness
    Splash into poolside fun at this Catskill Mountains motel, where seasonal swimming meets adventure in a charming outdoor oasis.
The price is ₹14,858
₹16,641 total
includes taxes & fees
2 Nov - 3 Nov
The Graham & Co.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Ashland

Breakfast included
4 stars

Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

8/10 Good
"The breakfast choice is very limited."
Isaac 1-night trip
Posted 2 days ago
Hotel Vienna
The Graham & Co.

The Graham & Co.

10/10 Excellent
"My friend and I enjoyed staying at the bunk house a lot. We didn't spend a lot of time in town or around the property but it was very charming! Everyone was really friendly and helpful with any question we had. We will definitely be interested in coming back to stay again."
Karly 2-night trip
Posted 9 days 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.