Title: Chestnut Springs Vacation Packages | Holiday Packages & Trips 2026/2027 from Expedia.ca [Chestnut Springs Travel Guide](https://expedia.ca/Roseland-Chestnut-Springs.dx553248635976481526)[Hotels in Chestnut Springs](https://expedia.ca/Chestnut-Springs-Roseland-Hotels.0-n553248635976481526-0.Travel-Guide-Filter-Hotels)[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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestnut Springs Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Chestnut Springs Hotel Deals ![New Build! Log Cabin with Hot Tub in Wintergreen](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/874fe033_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Build! Log Cabin with Hot Tub in Wintergreen Wintergreen Resort VA 10/10 Exceptional! (9 reviews) Troy was the best! Reviewed on Feb 8, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F03%2F2026&endDate=22%2F03%2F2026&selected=119318633&PinnedHotelID=119318633&HadPinnedHotel=true®ionId=553248635976481526) [](https://expedia.ca/Hotel-Search?startDate=21%2F03%2F2026&endDate=22%2F03%2F2026&selected=119318633&PinnedHotelID=119318633&HadPinnedHotel=true®ionId=553248635976481526) ![4 BR cabin mins to trails & breweries pets welcome](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/w1021h678x3y3-264d8a13_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 4 BR cabin mins to trails & breweries pets welcome Roseland VA CA $263 CA $802 total Mar 8 - Mar 9 includes taxes & fees 9.4/10 Exceptional! (31 reviews) We enjoyed the house. It had plenty of space for all of us. The ping pong table was a hit! Reviewed on Feb 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=77100132&PinnedHotelID=77100132&HadPinnedHotel=true®ionId=553248635976481526) ![WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS](https://images.trvl-media.com/lodging/49000000/48840000/48830800/48830715/2a174ad4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS Wintergreen Resort VA 10/10 Exceptional! (85 reviews) Very clean, gorgeous views Reviewed on Mar 4, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F03%2F2026&endDate=22%2F03%2F2026&selected=48830715&PinnedHotelID=48830715&HadPinnedHotel=true®ionId=553248635976481526) [](https://expedia.ca/Hotel-Search?startDate=21%2F03%2F2026&endDate=22%2F03%2F2026&selected=48830715&PinnedHotelID=48830715&HadPinnedHotel=true®ionId=553248635976481526) [See all 1,272 properties in Chestnut Springs](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F03%2F2026&endDate=09%2F03%2F2026®ionId=553248635976481526) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Chestnut Springs vacation package cost? ### How do I get a cheap travel package to Chestnut Springs? ### Where should I stay in Chestnut Springs? ### What are the top hotels in Chestnut Springs? ### How far in advance should I book my Chestnut Springs vacation? ### What does an Expedia Chestnut Springs travel package include? ### What should I know before booking a Chestnut Springs travel package? ### Can I choose my airline with a Chestnut Springs Expedia vacation package? ### If I'm not able to travel, can I cancel my Chestnut Springs vacation package? ### Things to do ![Blue Ridge Parkway Bundle](https://mediaim.expedia.com/localexpert/47424635/e747fbdf-9fe0-482b-911d-12645246395c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Blue Ridge Parkway Self-Guided Audio Tour Bundle CA $33 per traveller [](https://expedia.ca/things-to-do/blue-ridge-parkway-self-guided-audio-tour-bundle.a47424635.activity-details) ![Shenandoah National Park Self-Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/5066297/ad8bf26c-4486-4473-a66d-7bf5f687ae3f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Shenandoah National Park Self-Guided Driving Audio Tour CA $23 per traveller **100%** of travellers recommend [](https://expedia.ca/things-to-do/shenandoah-national-park-self-guided-driving-audio-tour.a5066297.activity-details) [See all activities in Roseland](https://expedia.ca/things-to-do/search?rid=553248635976481526) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.