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://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 Chestnut Springs, VA from CA $490 ![](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 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-13&endDate=2025-10-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-14&endDate=2025-10-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-24&endDate=2025-10-26&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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/8c44b91f.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!" CA $225 CA $632 total includes taxes & fees Oct 15 - Oct 16 [](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/f9b08921.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) ![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) ### 4 BR cabin mins to trails & breweries pets welcome Chestnut Springs 9.6/10 Exceptional (28) "Perfect location and a great house " CA $315 CA $865 total includes taxes & fees Oct 14 - Oct 15 [](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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/9206cfcc.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." CA $286 CA $490 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-24-With-Wintergreen-Advantage.h102441532.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) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441541/63329b2d.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441541/48894831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Place 43 with Wintergreen Advantage Chestnut Springs CA $286 CA $502 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Place-43-With-Wintergreen-Advantage.h102441541.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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/820fcb7f.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) ### Three Ridges 64 With Wintergreen Advantage Chestnut Springs CA $286 CA $595 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-Three-Ridges-64-With-Wintergreen-Advantage.h119543302.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) ![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) ![Dining](https://images.trvl-media.com/lodging/108000000/107700000/107695200/107695197/e2095d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Court 08 with Wintergreen Advantage Chestnut Springs CA $419 CA $704 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-08-With-Wintergreen-Advantage.h107695197.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116440000/116437600/116437516/bef48694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/117000000/116440000/116437600/116437516/c9926640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116440000/116437600/116437516/9b6d737c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116440000/116437600/116437516/8a505fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen 5BR with Hot Tub, Sauna, Firepit Chestnut Springs 10/10 Exceptional (4) "Loved that everything was provided! We were very appreciative of the shampoo, soap, body wash, paper towels and toilet paper provided. It was all good quality and sufficient for our entire stay. We had a great stay!" CA $735 CA $1,516 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Roseland-Hotels-Wintergreen-5BR-With-Hot-Tub.h116437516.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) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119240000/119231300/119231246/a128f5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119240000/119231300/119231246/17949524.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) ### Three Ridges 05 With Wintergreen Advantage Chestnut Springs CA $419 CA $704 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Interior](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/4f311398.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) ![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) ### New Build! Log Cabin with Hot Tub in Wintergreen Chestnut Springs 10/10 Exceptional (2) "Well appointed kitchen, beautiful cabin!" CA $993 CA $1,799 total includes taxes & fees Oct 16 - Oct 17 [](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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441537/4842df3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441537/d9f781e4.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) ### Highridge Court 30 with Wintergreen Advantage Chestnut Springs CA $286 CA $502 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-30-With-Wintergreen-Advantage.h102441537.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=2025-10-27&endDate=2025-10-28®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/1000000/670000/663700/663617/932add2a_y.jpg) ### Howard Johnson by Wyndham Staunton 10/10 Excellent "good location" [](https://expedia.ca/Staunton-Hotels-Howard-Johnson-By-Wyndham-Staunton.h663617.Hotel-Information) ![Comfort Inn](//images.trvl-media.com/lodging/1000000/70000/64100/64084/2a69aac3_y.jpg) ### Comfort Inn 10/10 Excellent "Was very clean" [](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 "Quiet location. Minutes from downtown " [](https://expedia.ca/Staunton-Hotels-Avid-Hotels-Staunton.h17558.Hotel-Information) ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Terrific location. The room was very clean and comfortable. " [](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 "Very ckean" [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.Hotel-Information) ![Quality Inn Waynesboro - Skyline Drive](//images.trvl-media.com/lodging/1000000/30000/22300/22261/dedaf9e2_y.jpg) ### Quality Inn Waynesboro - Skyline Drive 10/10 Excellent "The staff were very helpful and friendly. They provided recommendations for local attractions and events. Rooms were quite and clean and the beds were comfortable. Breakfast was adequate. Check in and check out was quick and easy. Staff were very responsive to a room maintenance need. Would recommend and will stay there again." [](https://expedia.ca/Staunton-Hotels-Quality-Inn-Waynesboro.h22261.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 "The staff was amazing! So friendly and knowledgeable. Room comfortable and really well kept. " [](https://expedia.ca/Staunton-Hotels-Best-Western-Staunton-Inn.h18431.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 "Good location, clean rooms, very comfortable beds! The staff was extremely friendly and went so far as to make sure we had a great stay. " [](https://expedia.ca/Staunton-Hotels-Days-Inn-By-Wyndham-Waynesboro.h13044.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. [Modern Luxury Mountain Home within Wintergreen Retreat Collection](https://www.expedia.ca/Nellysford-Hotels-Modern-Luxury-Mountain-Home-Within-Wintergreen-Retreat-Collection.h60606685.Hotel-Information): Vacation home, 1-minute walk from Wintergreen Resort. Offers 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. Provides kitchens, a communal pool, and Smart TVs. [Hotel 24 South](https://www.expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information): Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. [Motel 6 Staunton, VA](https://www.expedia.ca/Staunton-Hotels-Motel-6-Staunton.h8977.Hotel-Information): Features daily, a seasonal outdoor pool, and free self parking. ### 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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