Title: Book the Best Hotels with POOL in Highland Lake in 2025 | Expedia.ca [Hotels in Highland Lake](https://expedia.ca/Highland-Lake-Hotels.d553248635975854126.Travel-Guide-Hotels)[Vacation Rentals in Highland Lake](https://expedia.ca/Highland-Lake-Vacation-Rentals.d553248635975854126.Travel-Guide-VacationRentals)[Highland Lake Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Lake.d553248635975854126.Car-Rental-Guide)[Highland Lake Vacation Packages](https://expedia.ca/Highland-Lake.d553248635975854126.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Highland Lake, NY from CA $145 ![](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 Highland Lake Hotels with a Pool Tonight [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635975854126&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975854126&startDate=2025-10-27&endDate=2025-10-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975854126&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975854126&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Highland Lake Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/3b40d2ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/4070f19d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/41b49dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/5214096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Monticello Monticello 9.4/10 Exceptional (600) "My mini vacation was excellent,staff was nice and friendly,clean room,very comfortable bed and breakfast good. Highly recommend that hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ZHANNA CA $206 CA $233 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Monticello-Hotels-Hampton-Inn-Monticello.h75030626.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/08fad23e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/0feb1084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/e1440092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/59ea02f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Matamoras/Milford Matamoras 8.8/10 Excellent (1002) "Love staying here" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jo-Ann CA $139 CA $151 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Matamoras-Hotels-Hampton-Inn-Matamoras-Milford.h2774574.Hotel-Information) ![Indoor pool, open 7 AM to 10 PM, free cabanas, sun loungers](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/95ef3af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/d6b9765c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/90e1f183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resorts World Catskills Casino Monticello 8.6/10 Excellent (1082) "It is a great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caonabo CA $205 CA $267 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 9:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/16000000/15760000/15750100/15750019/7a5792d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15760000/15750100/15750019/03ebbf02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15760000/15750100/15750019/d60340c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/16000000/15760000/15750100/15750019/c0d8ba6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Birches Hawley 8.6/10 Excellent (277) "Very nice accommodations with a beautiful lake. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelley CA $199 CA $282 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Hawley-Hotels-Silver-Birches.h15750019.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/1ff4f5d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/fc920cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/262d6215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Hunt's Landing Hotel Matamoras/Milford Matamoras 8.4/10 Very good (1005) "Great staff&great area for touring. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $133 CA $145 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Waterslide](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/w966h620x25y37-6819803f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/89050c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/w963h620x26y37-b83c1234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kartrite Resort & Indoor Waterpark Monticello 8.2/10 Very good (1772) "Nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana CA $167 CA $278 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/88000000/87420000/87410200/87410153/8caa80fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87420000/87410200/87410153/de035b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/88000000/87420000/87410200/87410153/720d2fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner and brunch served, alfresco dining ](https://images.trvl-media.com/lodging/88000000/87420000/87410200/87410153/a17bcc8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bradstan Boutique Hotel Eldred 9.8/10 Exceptional (99) "Lovely property to spend a weekend at. It’s secluded from the main area but the charm it has and the restaurant that’s present makes no need to leave the property. The breakfast and ambiance to spend during the fall and winter months make it cozy and warm" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $544 CA $636 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Eldred-Hotels-The-Eldred-Preserve.h87410153.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/cd3eed20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/91f35d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/399979ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Kitchenette (Living Room;with Sofabed)](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/2c9f1032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Monticello Monticello 8.2/10 Very good (1003) "Our go to spot when in Monticello NY.the staff was wonderful, Breakfast was terrific " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joe CA $159 CA $180 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/32000000/31880000/31874000/31873964/42d7329b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/32000000/31880000/31874000/31873964/1c6a7d13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31880000/31874000/31873964/341c200a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31880000/31874000/31873964/be5b65ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### YO1 Longevity & Health Resorts, Catskills Monticello 8.0/10 Very good (495) "Quick stay but wonderful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $467 CA $528 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Monticello-Hotels-YO1-Health-Resort.h31873964.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/a57b1b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/2696141a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bars/lounges](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/9db559da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/1bb15d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alder at Resorts World Catskills Monticello 8.2/10 Very good (188) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darshan CA $173 CA $231 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.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=2025-11-09&endDate=2025-11-10®ionId=553248635975854126&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Highland Lake Hotel Reviews ![Best Western Hunt's Landing Hotel Matamoras/Milford](//images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "Barbara does an excellent job with the breakfast! Plenty of hot food items and delirious options. She keeps it full and clean. She deserves a raise." [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Villa Roma Resort and Conference Center](//images.trvl-media.com/lodging/1000000/910000/902000/901998/2e43c618_y.jpg) ### Villa Roma Resort and Conference Center 10/10 Excellent "We had a great stay, large beautiful and well maintained area, lots of interesting activities, kids loved every moment" [](https://expedia.ca/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information) ![Hampton Inn Matamoras/Milford](//images.trvl-media.com/lodging/3000000/2780000/2774600/2774574/e1440092_y.jpg) ### Hampton Inn Matamoras/Milford 10/10 Excellent " Friendly" [](https://expedia.ca/Matamoras-Hotels-Hampton-Inn-Matamoras-Milford.h2774574.Hotel-Information) ![Days Inn by Wyndham Wurtsboro](//images.trvl-media.com/lodging/1000000/40000/34300/34237/3073e3e0_y.jpg) ### Days Inn by Wyndham Wurtsboro 10/10 Excellent "We had a great experience and very nice hotel staff. Very comfortable clean and we loved the complimentary breakfast. We will go back again when we visit New York. Thanks again to the hotel owners and staff!" [](https://expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) ![Days Inn by Wyndham Liberty](//images.trvl-media.com/lodging/1000000/20000/19400/19381/e60bb869_y.jpg) ### Days Inn by Wyndham Liberty 10/10 Excellent "Place was quiet, clean and safe" [](https://expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Liberty.h19381.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Highland Lake? > [The Kartrite Resort & Indoor Waterpark](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information): Hotel, 7-minute walk from Resorts World Catskills. Features a children's pool, an indoor pool, and a water park. [Resorts World Catskills Casino](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information): Hotel, 4-minute walk from Resorts World Catskills. Offers 6 restaurants, a pool, and a full-service spa. [Best Western Hunt's Landing Hotel Matamoras/Milford](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information): Provides buffet, an indoor pool, and free self parking. [Villa Roma Resort and Conference Center](https://www.expedia.ca/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information): Features a children's pool, a seasonal outdoor pool, and 3 restaurants. [Hampton Inn Matamoras/Milford](https://www.expedia.ca/Matamoras-Hotels-Hampton-Inn-Matamoras-Milford.h2774574.Hotel-Information): Offers buffet, an indoor pool, and complimentary wired internet access. ### What is there to see and do in Highland Lake? > Make a point to visit attractions like The Kartrite Resort & Indoor Waterpark and Costa's Family Fun Park. Discover sights such as Sidwell Lake during your stay. ### When is the best time to book a hotel with a pool in Highland Lake? > Taking into account the local weather in Highland Lake can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Highland Lake are January, February, December, and March, with each month seeing an average of 9 inches of snowfall. ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Beach Hotel Hotels in Barryville](https://www.expedia.ca/Barryville-Hotels-Beach-Hotel.0-0-d6069726-tBeachHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Barryville](https://www.expedia.ca/Barryville-Hotels-Casino-Hotel.0-0-d6069726-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Barryville](https://www.expedia.ca/Barryville-Hotels-Hotel-With-Pool.0-0-d6069726-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Barryville](https://www.expedia.ca/Barryville-Hotels-Luxury-Hotel.0-0-d6069726-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Barryville](https://www.expedia.ca/Barryville-Hotels-Spa-Hotel.0-0-d6069726-tSpaHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bethel](https://www.expedia.ca/Bethel-Hotels-Cheap-Hotels.0-0-d553248635077688906-tCheapHotels.Travel-Guide-Filter-Hotels) - 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