Search Hotels with Pool in Ashland

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Check availability on Ashland Hotels with Pool

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Ashland hotels with a pool

Seasonal outdoor pool
The Graham & Co.

The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.6 out of 10, Exceptional, (22)
"Great place to stay when in the area, lovely staff would definitely stay here again."
United States
Paul
The price is ฿4,819
฿5,397 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Graham & Co.
Indoor pool
Hotel Vienna

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (728)
"Great service, nice and clean hotel."
United States
Mary
Hotel Vienna
Seasonal outdoor pool, pool umbrellas, pool loungers
The Colonial Motel

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.4 out of 10, Exceptional, (406)
"Comfortable, quiet and good value vs other options in the region. "
United States
Karl
The price is ฿2,769
฿3,045 total
includes taxes & fees
20 Jan - 21 Jan 2026
The Colonial Motel
Seasonal outdoor pool
Catskill Seasons Inn

Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.2 out of 10, Very good, (241)
"Great Stay would definitely recommend "
United States
Jay
The price is ฿4,630
฿5,185 total
includes taxes & fees
7 Jan - 8 Jan 2026
Catskill Seasons Inn
Outdoor pool
Moore's Motel

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (158)
"Stay here every time we are in the area. And its always a great stay and a good time down the street at the prattsville tavern. Moores is excellent"
United States
John
The price is ฿3,729
฿4,027 total
includes taxes & fees
1 Jan - 2 Jan 2026
Moore's Motel
Seasonal outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas
Emerson Resort & Spa

Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.2 out of 10, Wonderful, (46)
"Very clean and cozy "
United States
Robert
The price is ฿7,429
฿9,153 total
includes taxes & fees
5 Jan - 6 Jan 2026
Emerson Resort & Spa
Outdoor pool
Kaatskill Mountain Club & Condos by Vail Resorts

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, (324)
"Beautiful resort. "
United States
Kelly
The price is ฿6,806
฿8,105 total
includes taxes & fees
6 Jan - 7 Jan 2026
Kaatskill Mountain Club & Condos by Vail Resorts
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

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, 2-minute walk from Hunter Mountain. Provides 2 hot tubs, an outdoor pool and a sauna. Kaatskill Mountain Club & Condos by Vail Resorts: Hotel located near Catskill Mountains. Offers a full-service spa, a seasonal outdoor pool and complimentary bicycles. Urban Cowboy Lodge: Hotel located near Windham Mountain Resort. Provides free self parking, a seasonal outdoor pool and complimentary bicycles. Eastwind Windham: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Ashland?
Explore places such as Hunter Mountain while you're in the area. Make a point to visit attractions such as Mountain Top Arboretum and Hobart Book Village.
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.