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Ashland Hotels with Swimming Pool

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Check availability on Ashland Hotels with Swimming Pools

Tonight
12 Aug - 13 Aug
Tomorrow
13 Aug - 14 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Ashland hotels with a pool

1. 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.
RM491
RM530 total
includes taxes & fees
13 Aug - 14 Aug
Moore's Motel

2. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
RM545
RM659 total
includes taxes & fees
7 Sept - 8 Sept
Hotel Vienna

3. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
RM365
RM401 total
includes taxes & fees
16 Aug - 17 Aug
The Colonial Motel

4. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
RM682
RM736 total
includes taxes & fees
16 Aug - 17 Aug
The Winwood Condominiums

5. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
RM893
RM1,169 total
includes taxes & fees
24 Aug - 25 Aug
Wylder Hotel Windham

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.
RM849
RM1,011 total
includes taxes & fees
24 Aug - 25 Aug
Kaatskill Mountain Club & Condos by Vail Resorts

7. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Serene seasonal pool oasis nestled in the Catskill Mountains offers perfect summer refreshment.
RM655
RM733 total
includes taxes & fees
13 Aug - 14 Aug
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
"the back decks and the path"
Bradford 2-night trip
Posted 4 hours ago
Hotel Vienna
The Graham & Co.

The Graham & Co.

10/10 Excellent
"This was my family’s third time staying at the Graham & Co. and every single stay has been wonderful. My family has grown a lot since our first stay 10 years ago, so staying in the bungalow gave everyone enough space while keeping us close. The room and grounds are very clean and well kept. The staff were so attentive. We arrived very late and they were great about giving us an option of seamless access to our room. We will certainly be back soon."
Lakesha 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: Offers a full-service spa, a seasonal outdoor pool and complimentary bicycles. Emerson Resort & Spa: Hotel located near Windham Mountain Resort. Provides free self parking, a seasonal outdoor pool and complimentary bicycles. Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Offers daily, an indoor pool and free self parking. Urban Cowboy Lodge: Hotel, 1-minute walk from Hunter Mountain. Features 2 hot tubs, an outdoor pool and a sauna. Hotel Vienna: 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 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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