Title: Book the Best Hotels with POOL in Ashland in 2026 | Expedia.ca [Hotels in Ashland](https://expedia.ca/Ashland-Hotels.d3000422181.Travel-Guide-Hotels)[Vacation Rentals in Ashland](https://expedia.ca/Ashland-Vacation-Rentals.d3000422181.Travel-Guide-VacationRentals)[Ashland Car Rentals](https://expedia.ca/Car-Rentals-In-Ashland.d3000422181.Car-Rental-Guide)[Ashland Vacation Packages](https://expedia.ca/Ashland.d3000422181.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Ashland, NY from CA $135 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Ashland Hotels with a Pool Tonight [Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=3000422181&startDate=2025-12-08&endDate=2025-12-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=3000422181&startDate=2025-12-09&endDate=2025-12-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000422181&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000422181&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Ashland Hotels with a Pool ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/497f4120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bungalow | Private kitchen](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/b40da561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/274754e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/69ba57d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Graham & Co. Phoenicia 9.6/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $214 CA $240 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Phoenicia-Hotels-The-Graham-Co.h17412349.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/20000000/19340000/19335900/19335876/2cb998ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19340000/19335900/19335876/ccb15199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19340000/19335900/19335876/2878762c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 3 Bedrooms | Living area](https://images.trvl-media.com/lodging/20000000/19340000/19335900/19335876/d9f6397c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Catskill Seasons Inn Shandaken 8.2/10 Very good (240) "Great Stay would definitely recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $164 CA $184 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Kingston-Hotels-Catskill-Seasons-Inn.h19335876.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/c06d6be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/w750h561x0y0-3802df97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hiking](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/d446595a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vienna Windham 9.4/10 Exceptional (716) "Great place to stay with family room it's very clear 👌" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jaisson [](https://www.expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/213defa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/8751513e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/18664b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/daa928ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Motel Grand Gorge 9.4/10 Exceptional (405) "Comfortable, quiet and good value vs other options in the region. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karl CA $123 CA $135 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/cdf3c752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Paper towels](https://images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/c74e4dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/d9928411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57230000/57228600/57228597/02023cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kaatskill Mountain Club at Hunter Mountain Hunter 9.2/10 Wonderful (318) "Beautiful resort. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $273 CA $325 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Kingston-Hotels-Hunter-Mountain-Resort.h57228597.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/a20af6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/10cb851a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/effd9ea0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/0d893f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moore's Motel Prattsville 8.6/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $166 CA $179 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Prattsville-Hotels-Moores-Motel.h16545641.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/f9b90241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/72e324d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/593e8eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, books](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/256f5f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge Hunter Highlands 9.8/10 Exceptional (6) "Great stay! We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $137 CA $299 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Hunter-Hotels-Catskill-Oasis-II-The-Only-True-Ski-InOut-On-Mtn.h89604830.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/d6e9603b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/0e189703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/fbbd36bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, steam room, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/39000000/38030000/38029000/38028935/c60350a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Emerson Resort & Spa Mount Tremper 9.2/10 Wonderful (46) "Very clean and cozy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $330 CA $407 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Kingston-Hotels-Emerson-Resort-Spa.h38028935.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/114000000/113560000/113557300/113557289/941fa5de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113560000/113557300/113557289/575276c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113560000/113557300/113557289/f2135e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113560000/113557300/113557289/c7cbb269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Only Ski In Out on Hunter Mtn | Panoramic Views! Hike, Golf, Fish, Unwind! Lanesville 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin C. CA $151 CA $316 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Hunter-Hotels-Catskill-Oasis-III-Only-Ski-InSki-Out-Hunter-Mtn.h113557289.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/9a683bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/1ad206d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/5e7a20ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/ce5990b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winwood Condominiums by Windham Mountain Club Windham 8.8/10 Excellent (344) "convenient nice and clean residence with kitchen and market nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jatin CA $247 CA $267 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-22&endDate=2025-12-23®ionId=3000422181&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Ashland Hotel Reviews ![Catskill Seasons Inn](https://images.trvl-media.com/lodging/20000000/19340000/19335900/19335876/9f9d136f_y.jpg) ### Catskill Seasons Inn 10/10 Excellent "Clean room " [](https://expedia.ca/Kingston-Hotels-Catskill-Seasons-Inn.h19335876.Hotel-Information) ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Great place for local skiing. Very little local wifi coverage so make sure you have all your check-in details in advance. Nice spot." [](https://expedia.ca/Kingston-Hotels-Hotel-Vienna.h893228.Hotel-Information) ![The Graham & Co.](https://images.trvl-media.com/lodging/18000000/17420000/17412400/17412349/497f4120_y.jpg) ### The Graham & Co. 10/10 Excellent "Amazing rustic getaway. They go above and beyond to ensure you are taken care of. Absolutely great experience, highly recommend." [](https://expedia.ca/Phoenicia-Hotels-The-Graham-Co.h17412349.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Ashland? ### What is there to see and do in Ashland? ### When is the best time to book a hotel with a pool in Ashland? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Hensonville ](https://www.expedia.ca/4Star-Hensonville-Hotels.s40-0-d6023521.Travel-Guide-Filter-Hotels) - [Business Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany ](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Albany ](https://www.expedia.ca/Albany-Hotels-Hotels-With-Bar.0-0-d603260-tHotelswithBar.Travel-Guide-Filter-Hotels) - 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