Title: Book the Best Hotels with POOL in Chestnut Springs in 2025 | Expedia.ca [Chestnut Springs Travel Guide](https://expedia.ca/Roseland-Chestnut-Springs.dx553248635976481526)[Vacation Rentals in Roseland](https://expedia.ca/Roseland-Vacation-Rentals.d6361484.Travel-Guide-VacationRentals)[Things to do in Roseland](https://expedia.ca/Things-To-Do-In-Roseland.d6361484.Travel-Guide-Activities)[Chestnut Springs Car Rentals](https://expedia.ca/Car-Rentals-In-Chestnut-Springs.d553248635976481526.Car-Rental-Guide)[Chestnut Springs Vacations](https://expedia.ca/Chestnut-Springs.d553248635976481526.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 Chestnut Springs, VA from CA $499 ![](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 Chestnut Springs Hotels with a Pool Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-30&endDate=2025-10-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestnut Springs Hotels with a Pool ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/448c50fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/52e5512c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/4e7f6a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/b5ed2b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Retreat: Cabin with Hot Tub, Nestled in Woods, Hiking, Game Room Chestnut Springs 10/10 Exceptional (13) "We enjoyed the space, amenities and location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) eric r. CA $224 CA $641 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Roseland-Hotels-Wintergreen-Retreat-Cozy-Cabin-With-Hot-Tub.h101916242.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/add548d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/57b1d668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/264d8a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/05a5f823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 BR cabin mins to trails & breweries pets welcome Chestnut Springs 9.6/10 Exceptional (28) "Perfect location and a great house " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan M. CA $270 CA $823 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Nellysford-Hotels-4-BR-Cabin-Mins-To-Trails-Breweries-Pets-Welcome.h77100132.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/a13f8427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/aed55363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/d27b0647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/3500e79c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Court 24 with Wintergreen Advantage Chestnut Springs 8.0/10 Very good (1) "Nice place with a great view. Take your own Keurig machine though." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James C. CA $284 CA $499 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-24-With-Wintergreen-Advantage.h102441532.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/0cbe3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/cd4f8621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/ede09bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/820fcb7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Ridges 64 With Wintergreen Advantage Chestnut Springs CA $284 CA $593 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Nellysford-Hotels-Three-Ridges-64-With-Wintergreen-Advantage.h119543302.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441541/78f4d01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441541/83a20360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441541/48894831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441541/4d1ea9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Place 43 with Wintergreen Advantage Chestnut Springs CA $284 CA $499 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Place-43-With-Wintergreen-Advantage.h102441541.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/108000000/107700000/107695200/107695197/44607272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107700000/107695200/107695197/d7b5f1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107700000/107695200/107695197/1114b345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107700000/107695200/107695197/72d49fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Court 08 with Wintergreen Advantage Chestnut Springs CA $417 CA $701 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-08-With-Wintergreen-Advantage.h107695197.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/120000000/119240000/119231300/119231246/5c18adf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/120000000/119240000/119231300/119231246/b50ed825.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/120000000/119240000/119231300/119231246/f93d63a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119240000/119231300/119231246/a128f5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Ridges 05 With Wintergreen Advantage Chestnut Springs CA $417 CA $701 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Roseland-Hotels-Three-Ridges-05-With-Wintergreen-Advantage.h119231246.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/874fe033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/c8287959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/d3789b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/0d82e1fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Build! Log Cabin with Hot Tub in Wintergreen Chestnut Springs 10/10 Exceptional (2) "Well appointed kitchen, beautiful cabin!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Curtis [](https://www.expedia.ca/Nellysford-Hotels-New-Build-Log-Cabin-With-Hot-Tub-In-Wintergreen.h119318633.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441537/6e8cb0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441537/70db5b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441537/4842df3a.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/103000000/102450000/102441600/102441537/f4b06443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Court 30 with Wintergreen Advantage Chestnut Springs CA $284 CA $500 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-30-With-Wintergreen-Advantage.h102441537.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441739/354c5d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441739/176dfcfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441739/2478b44d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441739/c5f602f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Place 42 with Wintergreen Advantage Chestnut Springs CA $417 CA $703 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Place-42-With-Wintergreen-Advantage.h102441739.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=2025-11-13&endDate=2025-11-14®ionId=553248635976481526&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chestnut Springs Hotel Reviews ![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 "I always stay here when visiting family in Staunton. The main reason? Because of the service!! They are so nice and accommodating! Yes, it is older and dated a bit, but they recently gave the place a fresh paint job and are doing their best. Thank you" [](https://expedia.ca/Staunton-Hotels-Howard-Johnson-By-Wyndham-Staunton.h663617.Hotel-Information) ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Beautiful downtown location. We loved the charm of the area." [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Best Western Staunton Inn](//images.trvl-media.com/lodging/1000000/20000/18500/18431/5e29fbfa_y.jpg) ### Best Western Staunton Inn 10/10 Excellent "Always a comfortable place to stay when we come home. " [](https://expedia.ca/Staunton-Hotels-Best-Western-Staunton-Inn.h18431.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) ![Comfort Inn](//images.trvl-media.com/lodging/1000000/70000/64100/64084/2a69aac3_y.jpg) ### Comfort Inn 10/10 Excellent "Breakfast is good." [](https://expedia.ca/Staunton-Hotels-Comfort-Inn.h64084.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) ![Comfort Inn & Suites Staunton](//images.trvl-media.com/lodging/1000000/10000/4300/4272/f4b37015_y.jpg) ### Comfort Inn & Suites Staunton 10/10 Excellent "Really clean . Rooky room" [](https://expedia.ca/Staunton-Hotels-Comfort-Inn-Suites.h4272.Hotel-Information) ![Days Inn by Wyndham Staunton](//images.trvl-media.com/lodging/1000000/30000/20600/20577/f55abd3f_y.jpg) ### Days Inn by Wyndham Staunton 10/10 Excellent "Was a bit nervous upon arrival because the building itself reminded me of the Days Inn in my Hometown, which is " [](https://expedia.ca/Staunton-Hotels-Days-Inn-By-Wyndham-Staunton.h20577.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Chestnut Springs? > [New Build! Log Cabin with Hot Tub in Wintergreen](https://www.expedia.ca/Nellysford-Hotels-New-Build-Log-Cabin-With-Hot-Tub-In-Wintergreen.h119318633.Hotel-Information): Features complimentary wireless internet access, a communal pool, and kitchens. [4 BR cabin mins to trails & breweries pets welcome](https://www.expedia.ca/Nellysford-Hotels-4-BR-Cabin-Mins-To-Trails-Breweries-Pets-Welcome.h77100132.Hotel-Information): Vacation home, 1-minute walk from Wintergreen Resort. Offers kitchens, a communal pool, and Smart TVs. [Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly](https://www.expedia.ca/Roseland-Hotels-Luxury-5Bd-4Ba-Sleeps-16-Hot-TubDog-Friendly.h99504525.Hotel-Information): Vacation home, 12-minute walk from Wintergreen Resort. Provides complimentary wireless internet access, a communal pool, and kitchens. [Sleep Inn Staunton](https://www.expedia.ca/Staunton-Hotels-Sleep-Inn-Staunton.h168389.Hotel-Information): Offers daily, a seasonal outdoor pool, and free self parking. [Howard Johnson by Wyndham Staunton](https://www.expedia.ca/Staunton-Hotels-Howard-Johnson-By-Wyndham-Staunton.h663617.Hotel-Information): Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. ### What is there to see and do in Chestnut Springs? > Make a point to visit attractions like Sherando Lake Recreation Area and Wildlife Center of Virginia. Discover sights such as Wintergreen Resort during your stay. ### When is the best time to book a hotel with a pool in Chestnut Springs? > You may want to consider a place to stay that has an outdoor pool if you're planning to visit in the hottest months of July, August, or June when the average temperature is 73°F. 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