Find Hotels with a Pool in Ashland, NY

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Check availability on Ashland Hotels with a Pool

Top Ashland Hotels with a Pool

Indoor pool
Hotel Vienna

Hotel Vienna

2.5 star property
Windham
  • Indoor pool
9.4 out of 10, Exceptional, (699)
Crystal-clear waters beckon at the indoor aquatic sanctuary, perfect for unwinding after mountain adventures. Complimentary bicycles await outside while spotless rooms offer balconies overlooking breathtaking woodland scenery and nearby ski slopes.
Hotel Vienna
Seasonal outdoor pool
The Graham & Co.

The Graham & Co.

3.0 star property
Phoenicia
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.6 out of 10, Exceptional, (20)
Mountain adventures begin poolside at this charming Catskills retreat. Seasonal swimming pairs perfectly with complimentary bicycle rentals for exploring nearby hiking trails. Evenings transform with the glow of the firepit and entertainment in the arcade room.
The price is NT$4,254
NT$4,765 total
includes taxes & fees
Dec 15 - Dec 16
The Graham & Co.
Seasonal outdoor pool, pool umbrellas, sun loungers
The Colonial Motel

The Colonial Motel

2.5 star property
Grand Gorge
  • Pool loungers
9.4 out of 10, Exceptional, (402)
Surrounded by outdoor adventures from Mine Kill State Park to ski resorts, this motel offers a pristine seasonal pool complete with sun loungers and umbrellas. Clean, individually decorated rooms provide a cozy mountain retreat.
The price is NT$2,768
NT$3,044 total
includes taxes & fees
Dec 15 - Dec 16
The Colonial Motel
Seasonal outdoor pool
Catskill Seasons Inn

Catskill Seasons Inn

2.5 star property
Shandaken
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.2 out of 10, Very Good, (236)
Sparkling seasonal pool waters invite summer relaxation amid picturesque mountain surroundings. Guests appreciate the peaceful grounds, complimentary continental breakfast featuring fresh bagels, and modern, spacious accommodations with premium bedding.
The price is NT$3,697
NT$4,140 total
includes taxes & fees
Dec 15 - Dec 16
Catskill Seasons Inn
Outdoor pool
Moore's Motel

Moore's Motel

2.5 star property
Prattsville
  • Outdoor pool
8.6 out of 10, Excellent, (158)
Crystal-clear waters beckon at the outdoor pool, where guests relish tranquil swims amid landscaped gardens. Barbecue grills nearby create opportunities for alfresco dining, complementing this exceptionally clean, comfortable retreat.
The price is NT$3,728
NT$4,026 total
includes taxes & fees
Nov 19 - Nov 20
Moore's Motel
Outdoor pool
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2.0 star property
Hunter
  • Outdoor pool
9.2 out of 10, Wonderful, (314)
Heated pool waters invite swimmers for a refreshing mountain escape with stunning views. Beyond aquatic amenities, this hotel offers a sauna, steam room, and access to Van Winkle's restaurant serving outstanding American cuisine.
The price is NT$6,139
NT$7,310 total
includes taxes & fees
Nov 17 - Nov 18
Kaatskill Mountain Club at Hunter Mountain
Outdoor pool
Wylder Hotel Windham

Wylder Hotel Windham

3.5 star property
Windham
  • Outdoor pool
8.8 out of 10, Excellent, (79)
Seasonal outdoor pool creates a refreshing summer sanctuary after exploring nearby mountain trails. Beyond swimming, guests enjoy complimentary bicycles, an on-site restaurant with happy hour, and cozy rooms equipped with bathrobes and modern comforts.
The price is NT$4,729
NT$6,661 total
includes taxes & fees
Nov 16 - Nov 17
Wylder Hotel Windham
Seasonal outdoor pool
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3.0 star property
Windham
  • Pool
  • Parking included
  • Free WiFi
  • Game room
  • Laundry
  • Housekeeping
8.8 out of 10, Excellent, (343)
Mountainside relaxation awaits at the seasonal outdoor pool, perfect for summer splashes between skiing adventures. With ski shuttle service, passes, and nearby hiking trails, this hotel balances aquatic refreshment with alpine exploration.
The price is NT$5,250
NT$5,670 total
includes taxes & fees
Nov 16 - Nov 17
Winwood Condominiums by Windham Mountain Club
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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Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Room was nice and clean. The staff was beyond friendly and made me feel comfortable and welcomed. Would definitely stay here again!"
Jessica 2-night trip
Posted 6 days ago
Hotel Vienna

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Frequently asked questions

What are some hotels with pools in Ashland?
Hunter Lodge, a Bluebird by Lark: Hotel located near Windham Mountain Resort. Offers daily, an indoor pool, and free self parking. Hotel Vienna: Hotel, 13-minute walk from Hunter Mountain. Provides a sauna, an outdoor pool, and complimentary wireless internet access. Kaatskill Mountain Club at Hunter Mountain: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool, and complimentary bicycles. Urban Cowboy Lodge: Hotel located near Catskill Mountains. Offers continental, a seasonal outdoor pool, and free self parking. Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access.
What is there to see and do in Ashland?
Explore places like Hunter Mountain while you're in the area. Make a point to visit attractions like Mountain Top Arboretum and Hobart Book Village.
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.