Title: Book the Best BOUTIQUE Hotels 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 Boutique Hotels in Chestnut Springs, VA from CA $491 ![](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 Boutique Hotels Tonight [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-18&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-19&endDate=2025-10-20&adults=2&propertyStyle=BOUTIQUE&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&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976481526&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestnut Springs Boutique Hotels We don't have any properties that match your exact search [See all properties in Chestnut Springs](https://expedia.ca/Hotel-Search?startDate=2025-11-01&endDate=2025-11-02®ionId=553248635976481526&adults=2) ## Recommended hotels in Chestnut Springs ![Exterior](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/30daf106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/f4ae5de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/a1d8182f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/870c116d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Ridge Retreat Chestnut Springs 9.0/10 Wonderful (4) "Enjoyed our stay, the property was very nice, communicated with property manager regarding a few issues and they were responsive. Accommodated the number of guests we had. Could use a bigger parking area for amount of guests that could be accommodated. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy N. CA $379 CA $805 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Roseland-Hotels-New-Hot-Tub-Wintergreen-Resort-Ski-Spa.h108916763.Hotel-Information) ![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/102000000/101920000/101916300/101916242/4e7f6a35.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) ![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) ### 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 $228 CA $651 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) ![Dining](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/05a5f823.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) ### 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 $315 CA $883 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-4-BR-Cabin-Mins-To-Trails-Breweries-Pets-Welcome.h77100132.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/ede09bc5.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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/820fcb7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/0cbe3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Ridges 64 With Wintergreen Advantage Chestnut Springs CA $286 CA $596 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-Three-Ridges-64-With-Wintergreen-Advantage.h119543302.Hotel-Information) ![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) ![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) ### Highridge Place 43 with Wintergreen Advantage Chestnut Springs CA $286 CA $503 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Place-43-With-Wintergreen-Advantage.h102441541.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/3500e79c.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/9206cfcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441532/a13f8427.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 $287 CA $491 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-24-With-Wintergreen-Advantage.h102441532.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107700000/107695200/107695197/72d49fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Highridge Court 08 with Wintergreen Advantage Chestnut Springs CA $419 CA $705 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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119240000/119231300/119231246/17949524.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) ![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) ### Three Ridges 05 With Wintergreen Advantage Chestnut Springs CA $419 CA $705 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Roseland-Hotels-Three-Ridges-05-With-Wintergreen-Advantage.h119231246.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102441600/102441537/d9f781e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 $287 CA $504 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Nellysford-Hotels-Highridge-Court-30-With-Wintergreen-Advantage.h102441537.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441739/2478b44d.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) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441739/d981fc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441739/354c5d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Highridge Place 42 with Wintergreen Advantage Chestnut Springs CA $419 CA $702 total includes taxes & fees Oct 30 - Oct 31 [](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=2025-11-01&endDate=2025-11-02®ionId=553248635976481526&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chestnut Springs Hotel Reviews ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Awesome" [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Chestnut Springs? > After you've decided where to stay, figure out some fun things to do on your trip. Activities and attractions to experience around Chestnut Springs include Wintergreen Resort, Frontier Culture Museum, and Shenandoah Valley Art Center. You might also like to explore more of the area and take in additional sights like Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course, and Wayne Theatre while you're here. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Deer Springs](https://www.expedia.ca/2Star-Deer-Springs-Nellysford-Hotels.s20-n553248635976470298-0.Travel-Guide-Filter-Hotels) - [Apartments in Afton](https://www.expedia.ca/Afton-Apartments.d6056907-aaApartments.Travel-Guide-Accommodation) - [Cheap Hotels in Afton](https://www.expedia.ca/Afton-Hotels-Cheap-Hotels.0-0-d6056907-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Afton](https://www.expedia.ca/Afton-Hotels-Hotels-With-Bar.0-0-d6056907-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Afton](https://www.expedia.ca/Afton-Hotels-Mountain-Hotels.0-0-d6056907-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Afton](https://www.expedia.ca/Afton-Hotels-Pet-Friendly-Hotel.0-0-d6056907-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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