Hotels with Pool & Resorts in Ashland from AU$146

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Check availability on Ashland Hotels with Pool

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

Our top choices for Ashland hotels with a pool

Terrace/patio
The Graham & Co.

The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.6 out of 10, Exceptional, (22)
"A beautiful and relaxing getaway in the Catskills. Highly recommended. The room and grounds are clean and well maintained. The staff is friendly and attentive without being intrusive."
United States
Brian
The price is AU$259
includes taxes & fees
4 Jan - 5 Jan 2026
The Graham & Co.
Indoor pool
Hotel Vienna

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (726)
"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 AU$146
includes taxes & fees
28 Dec - 29 Dec
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 AU$249
includes taxes & fees
4 Jan - 5 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 AU$193
includes taxes & fees
31 Dec - 1 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 AU$426
includes taxes & fees
4 Jan - 5 Jan 2026
Emerson Resort & Spa
Pool
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge

Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge

Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
Hunter Highlands
9.8 out of 10, Exceptional, (9)
"Great stay! We will be back!"
United States
Michael
The price is AU$333
includes taxes & fees
20 Jan - 21 Jan 2026
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
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, (323)
"Beautiful resort. "
United States
Kelly
The price is AU$389
includes taxes & fees
6 Jan - 7 Jan 2026
Kaatskill Mountain Club & Condos by Vail Resorts
Pool
Only Ski In Out on Hunter Mtn | Panoramic Views! Hike, Golf, Fish, Unwind!

Only Ski In Out on Hunter Mtn | Panoramic Views! Hike, Golf, Fish, Unwind!

Only Ski In Out on Hunter Mtn | Panoramic Views! Hike, Golf, Fish, Unwind!
Lanesville
10.0 out of 10, Exceptional, (1)
"Such a great one bedroom, ski in/out it was right on the Highlands trail. Place was newly done lots of fresh wood. The electric heater and fireplace is super cute! Nice big shower we really enjoyed it."
United States
Kristin C.
The price is AU$353
includes taxes & fees
21 Jan - 22 Jan 2026
Only Ski In Out on Hunter Mtn | Panoramic Views! Hike, Golf, Fish, Unwind!
Outdoor pool
Wylder Hotel Windham

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.6 out of 10, Excellent, (89)
"Spotless room and great staff "
United States
Josue
The price is AU$406
includes taxes & fees
25 Dec - 26 Dec
Wylder Hotel Windham
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
"Great Spacious Room. The Front Desk Staff were super welcoming and very helpful. Highly Recommended. "
Arthur 1-night trip
Posted 2 days ago
Hotel Vienna

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.