Title: Book the Best Hotels with POOL in Wintergreen in 2025 | Expedia.ca [Hotels in Wintergreen](https://expedia.ca/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Vacation Rentals in Wintergreen](https://expedia.ca/Wintergreen-Vacation-Rentals.d10811.Travel-Guide-VacationRentals)[Things to do in Wintergreen](https://expedia.ca/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities)[Wintergreen Car Rentals](https://expedia.ca/Car-Rentals-In-Wintergreen.d10811.Car-Rental-Guide)[Wintergreen Vacation Packages](https://expedia.ca/Wintergreen.d10811.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/30888d0dcbd6b56a6c3164112bdde6d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rebecca Brent # Find Hotels with a Pool in Wintergreen, VA from CA $340 ![](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 Wintergreen Hotels with a Pool Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10811&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=10811&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=10811&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=10811&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wintergreen Hotels with a Pool ![Property grounds](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/29fa29ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/f81462f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/w1273h849x4y3-b64d948a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Modern Mountain Condo Wintergreen Resort 10/10 Exceptional (30) "Ideal location for skiing at Wintergreen. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashok G. CA $140 CA $340 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/eb46d699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/55159b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/c3acb08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/1b7442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Condo -Steps to Ski and restaurants Wintergreen Resort 9.8/10 Exceptional (26) "We had a great time and the place was just right." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula T. CA $160 CA $374 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Condo-Steps-To-Ski-And-Restaurants.h102325315.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/a67ce0ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/e8897717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/110502b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/b3014a69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers Lodge 26 with Wintergreen Advantage Wintergreen 10/10 Exceptional (2) "Love staying here! It’s so close to the slope and the staff is great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $237 CA $415 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Lodge-26-With-Wintergreen-Advantage.h107695259.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/41c181e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/5c8096d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/c1861718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/7b8c9b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers Studio 46 with Wintergreen Advantage Wintergreen 10/10 Exceptional (2) "We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madison D. CA $223 CA $377 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Studio-46-With-Wintergreen-Advantage.h102442095.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441971/39a5b118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441971/9ae27fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441971/9d3b42af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441971/ae5aa12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Inn Lodge 79 with Wintergreen Advantage Wintergreen 10/10 Exceptional (1) "The Wintergreen resort is beautiful, and this rented condo more than met our expectations. It was very clean and well-stocked with dishes/cookware/utensils/Keurig coffee machine, towels, hair dryers (2), and toiletries. The unit has two TVs complete with 123 cable channels. The bed in the loft is very comfortable. We plan to stay there again in the future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marlena E B. CA $237 CA $415 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Lodge-79-With-Wintergreen-Advantage.h102441971.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/c23d20f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/6e121a5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/8ed802b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/5a21de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Inn Studio 96 with Wintergreen Advantage Wintergreen 10/10 Exceptional (1) "A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lana CA $223 CA $379 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Studio-96-With-Wintergreen-Advantage.h102442025.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/b22c0c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/9f22b636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/580cf170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/2dc42b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers Lodge 54 with Wintergreen Advantage Wintergreen 8.0/10 Very good (1) CA $237 CA $415 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Lodge-54-With-Wintergreen-Advantage.h102442005.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/78b8767e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/81a26004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/81343878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/3c52de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Laurelwood Hollow: Walk to Ski & Swim Wintergreen Resort CA $133 CA $391 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/1751da82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/38271547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/67669396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/204d5911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Diamond Hill Studio 09 with Wintergreen Advantage Wintergreen CA $265 CA $437 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Diamond-Hill-Studio-09-With-Wintergreen-Advantage.h102442100.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441500/102441464/9260a936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441500/102441464/07de35eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/103000000/102450000/102441500/102441464/071dc69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102441500/102441464/1bc8b3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Ridges 74 with Wintergreen Advantage Wintergreen CA $286 CA $502 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Three-Ridges-74-With-Wintergreen-Advantage.h102441464.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=10811&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Wintergreen Hotel Reviews ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "The room was well prepared, clean and all amenities worked flawlessly." [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Holiday Inn Staunton Conference Center by IHG](//images.trvl-media.com/lodging/1000000/20000/19200/19125/c184cf6d_y.jpg) ### Holiday Inn Staunton Conference Center by IHG 10/10 Excellent "I have not had breakfast yet " [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.Hotel-Information) ![Days Inn by Wyndham Waynesboro](//images.trvl-media.com/lodging/1000000/20000/13100/13044/b02f560b_y.jpg) ### Days Inn by Wyndham Waynesboro 10/10 Excellent "I really enjoyed my stay." [](https://expedia.ca/Staunton-Hotels-Days-Inn-By-Wyndham-Waynesboro.h13044.Hotel-Information) ![avid hotel Staunton by IHG](//images.trvl-media.com/lodging/1000000/20000/17600/17558/3f6256d5_y.jpg) ### avid hotel Staunton by IHG 10/10 Excellent "The location, hotel, and staff were great. Parking was always convenient and the staff was always friendly and helpful! We will definitely stay there again. " [](https://expedia.ca/Staunton-Hotels-Avid-Hotels-Staunton.h17558.Hotel-Information) ![Howard Johnson by Wyndham Staunton](//images.trvl-media.com/lodging/1000000/670000/663700/663617/99b5e75e_y.jpg) ### Howard Johnson by Wyndham Staunton 10/10 Excellent "Front desk people were very helpful " [](https://expedia.ca/Staunton-Hotels-Howard-Johnson-By-Wyndham-Staunton.h663617.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Wintergreen? > [Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes](https://www.expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information): Condo, 1-minute walk from Wintergreen Resort. Features an indoor pool, an outdoor pool, and a full-service spa. [NEW! Warren's Woods! Cozy 5-bedroom house in fantastic Wintergreen Resort](https://www.expedia.ca/Nellysford-Hotels-NEW-Warrens-Woods-Spacious-5-Bedroom-House-In-Fantastic-Wintergreen-Resort.h118927334.Hotel-Information): Condo, 1-minute walk from Wintergreen Resort. Offers complimentary wireless internet access, a communal pool, and kitchens. [The Modern Mountain Condo](https://www.expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information): Condo, 1-minute walk from Wintergreen Resort. Features complimentary wireless internet access, a communal pool, and kitchens. [Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!](https://www.expedia.ca/Nellysford-Hotels-Modern-Luxe-Treetop-Retreat-WGas-Fire-Pit.h71969999.Hotel-Information): Vacation home, 1-minute walk from Wintergreen Resort. Offers complimentary wireless internet access, a communal pool, and kitchens. [Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK](https://www.expedia.ca/Nellysford-Hotels-Walk-To-SlopesLuxury-LivingSunset-Mountain-Views-And-Same-Day-Arrival-OK.h33563291.Hotel-Information): Vacation home, 1-minute walk from Wintergreen Resort. Features kitchens, a communal pool, and televisions. ### What is there to see and do in Wintergreen? > Spend some time experiencing the great outdoors at George Washington National Forest. Discover sights such as Wintergreen Resort during your stay. The mountain views and skiing are just some of the things to enjoy while you're in the area. ### When is the best time to book a hotel with a pool in Wintergreen? > You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Wintergreen in the warmest months of July, August, or June when the average temperature is 73°F. 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