Title: Book the Best Hotels with POOL in Chester Gap in 2025 | Expedia.ca [Chester Gap Travel Guide](https://expedia.ca/Chester-Gap.dx553248635975865285)[Hotels in Chester Gap](https://expedia.ca/Chester-Gap-Hotels.d553248635975865285.Travel-Guide-Hotels)[Vacation Rentals in Chester Gap](https://expedia.ca/Chester-Gap-Vacation-Rentals.d553248635975865285.Travel-Guide-VacationRentals)[Chester Gap Car Rentals](https://expedia.ca/Car-Rentals-In-Chester-Gap.d553248635975865285.Car-Rental-Guide)[Chester Gap Vacation Packages](https://expedia.ca/Chester-Gap.d553248635975865285.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/a636e33b71dd87047fd3a46ed8933b8f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brian V. Rowe # Find Hotels with a Pool in Chester Gap, VA from CA $89 ![](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 Chester Gap Hotels with a Pool Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&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=553248635975865285&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Gap Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b06f3533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/e0021d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/0f2ede5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA Winchester 8.8/10 Excellent (1006) "Our third stay here. Very nice and convenient to 81. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn CA $127 CA $139 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/2f833e8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ef7d5b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/71be8e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/4d102079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG Stephens City 8.2/10 Very good (784) "Very friendly staff, clean, would definitely stay again " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Christie CA $122 CA $132 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/64922bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows Front Royal 9.0/10 Wonderful (1002) "Nice place. Good bar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald CA $160 CA $180 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3837h2557x3y3-0ba96f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal Front Royal 9.0/10 Wonderful (1024) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irina CA $160 CA $178 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/dff66771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/0776aa15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/252865be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/055110cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Front Royal Front Royal 9.6/10 Exceptional (548) "Perfect for one night stay before Skyline Drive trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $165 CA $185 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/f4004e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/c5b2135d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/a2451115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/ff7a3bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Front Royal Near Shenandoah National Park Front Royal 6.4/10 (901) "nice for a great stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose CA $80 CA $89 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34060000/34056700/34056608/8d0e4bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/35000000/34060000/34056700/34056608/03a2dc43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mountain view](https://images.trvl-media.com/lodging/35000000/34060000/34056700/34056608/689bfb7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/35000000/34060000/34056700/34056608/b085c29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillside Luray 9.0/10 Wonderful (1002) "Clean rooms and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $140 CA $162 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Luray-Hotels-Hillside-Motel.h34056608.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/030e20be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/39d8617d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/2186fef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/08468627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twi-Lite Inn Front Royal 8.2/10 Very good (528) "Great pool and quiet area to stay in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $106 CA $118 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/29f2198e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/2df64736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/e8d6877f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/c77f2534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Strasburg Shenandoah Valley Strasburg 9.0/10 Wonderful (1001) "Great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $158 CA $176 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-Strasburg-Shenandoah-Valley.h2230885.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/dfc64d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/913756e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/f4aba607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4500/4419/9730f3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Stephens City - Winchester South Stephens City 8.0/10 Very good (614) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $108 CA $118 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn-Stephens-City-Winchester-South.h4419.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=2025-11-08&endDate=2025-11-09®ionId=553248635975865285&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Gap Hotel Reviews ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Our room was great and fresh. Dinner at the hotel restaurant was delicious and the staff was friendly and welcoming. " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Holiday Inn Express Winchester South-Stephens City by IHG](//images.trvl-media.com/lodging/1000000/40000/34400/34394/4d102079_y.jpg) ### Holiday Inn Express Winchester South-Stephens City by IHG 10/10 Excellent "It was good." [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Fairfield Inn & Suites Strasburg Shenandoah Valley](//images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/2df64736_y.jpg) ### Fairfield Inn & Suites Strasburg Shenandoah Valley 10/10 Excellent "Always a pleasure staying here " [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-Strasburg-Shenandoah-Valley.h2230885.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "Staff was friendly. Room was clean. Restaurant attached to hotel was tasty. Thumbs up." [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Baymont by Wyndham Front Royal Near Shenandoah National Park](//images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5_y.jpg) ### Baymont by Wyndham Front Royal Near Shenandoah National Park 10/10 Excellent "The staff was very friendly and helpful. The hotel is older but clean, quit and comfortable. The breakfast had a great variery and was well stocked. There was plenty of seating. We stayed for one night on our way to Shenandoah and Luray Caverns." [](https://expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "Very clean place. Wide variety of breakfast options. Decent options in the gym, not just a treadmill and elliptical. Clean pool. While the mattress was a little firmer than I would like (I like my mattresses soft), I would absolutely stay here again." [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Quality Inn Stephens City - Winchester South](//images.trvl-media.com/lodging/1000000/10000/4500/4419/9730f3d8_y.jpg) ### Quality Inn Stephens City - Winchester South 10/10 Excellent "Perfect" [](https://expedia.ca/Winchester-Hotels-Quality-Inn-Stephens-City-Winchester-South.h4419.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Always a great stay at this hotel. I highly recommend! " [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Twi-Lite Inn](//images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/39d8617d_y.jpg) ### Twi-Lite Inn 10/10 Excellent "Clean room , nice staff , comfortable beds . Great price . " [](https://expedia.ca/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chester Gap? > [Comfort Inn & Suites Winchester](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information): Offers buffet, an indoor pool, and complimentary wired internet access. [Country Inn & Suites by Radisson, Winchester, VA](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information): Provides a snack bar/deli, a pool, and daily. [Hampton Inn Front Royal](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information): Offers free self parking, an indoor pool, and complimentary wireless internet access. [Ramada by Wyndham Strasburg/Shenandoah Valley](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information): Offers daily, a seasonal outdoor pool, and free self parking. [DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information): Hotel located near Shenandoah National Park. Provides continental, a seasonal outdoor pool, and free self parking. ### What is there to see and do in Chester Gap? > Explore places like Shenandoah National Park while you're in Chester Gap. Make a point to visit attractions like Dinosaur Land and Secret Passage Ranch. ### When is the best time to book a hotel with a pool in Chester Gap? > You may want to think about an accommodation that offers an outdoor pool if you're planning to visit Chester Gap in the hottest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be what you want if you visit during the coldest months of January, February, or December when the average temperature is 37°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Hotels near Blue Ridge Shadows Golf Club](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Hotels.0-l553248621532661832-0.Travel-Guide-Filter-Hotels) - [Green Hotels in Virginia](https://www.expedia.ca/Destinations-In-Virginia-Green-Sustainable.0-0-d248-tGreenSustainable.Hotel-Filter-Destinations) - [Hotels with a Pool in Virginia](https://www.expedia.ca/Destinations-In-Virginia-Hotel-With-Pool.0-0-d248-tHotelwithPool.Hotel-Filter-Destinations) - [Hotels with Free Airport Shuttle in Virginia](https://www.expedia.ca/Destinations-In-Virginia-Hotels-With-Free-Airport-Shuttle.0-0-d248-tHotelswithFreeAirportShuttle.Hotel-Filter-Destinations) - [Hotels with Free Breakfast in Virginia](https://www.expedia.ca/Destinations-In-Virginia-Hotels-With-Free-Breakfast.0-0-d248-tHotelswithFreeBreakfast.Hotel-Filter-Destinations) - 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