Default HTG hotel image

Hotels with Swimming Pool in Ashland, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Ashland Hotels with Swimming Pool

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

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.
P7,176
P8,826 total
includes taxes & fees
Sep 14 - Sep 15
Hotel Vienna
Seasonal outdoor pool, pool umbrellas, sun loungers
Property entrance
Exterior
Lobby sitting area

2. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
P5,548
P6,102 total
includes taxes & fees
Sep 1 - Sep 2
The Colonial Motel
Outdoor pool
WiFi (free)
Meeting facility
Porch

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.
P7,472
P8,069 total
includes taxes & fees
Sep 1 - Sep 2
Moore's Motel
Seasonal outdoor pool
Exterior
Blackout drapes, WiFi (free), bed sheets
Living area

4. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
P11,151
P12,043 total
includes taxes & fees
Sep 1 - Sep 2
The Winwood Condominiums
Outdoor pool
Exterior
32-inch TV with cable channels
Exterior

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.
P11,690
P13,920 total
includes taxes & fees
Sep 30 - Oct 1
Kaatskill Mountain Club & Condos by Vail Resorts
Outdoor pool
Restaurant
Exterior
Exterior

6. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
P15,932
P20,320 total
includes taxes & fees
Sep 2 - Sep 3
Wylder Hotel Windham
Property amenity
Premium bedding, down comforters, iron/ironing board (on request)
Bathroom
Premium bedding, down comforters, iron/ironing board (on request)

7. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Serene seasonal pool oasis nestled in the Catskill Mountains offers perfect summer refreshment.
P9,962
P11,158 total
includes taxes & fees
Sep 1 - Sep 2
Catskill Seasons Inn
Seasonal outdoor pool
Terrace/patio
Fireplace
Front of property

8. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
P12,608
P14,121 total
includes taxes & fees
Oct 1 - Oct 2
Shandaken Inn
Terrace/patio
Fireplace
Front of property - evening/night
Property grounds

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.
P10,020
P11,223 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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"We really enjoyed the experience."
David 2-night trip
Posted 7 hours ago
Hotel Vienna
The Graham & Co.

The Graham & Co.

10/10 Excellent
"Wonderful Stay"
Daniel 2-night trip
Posted 5 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 setting 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 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.

Explore a world of travel with Expedia