Title: Chestnut Springs Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $2,305 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 ## Top Holiday Package Deals in Chestnut Springs Price found within the past 48 hours. Click for updated prices. ![Basecamp151](https://images.trvl-media.com/lodging/120000000/119790000/119781400/119781362/f6de3776_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Basecamp151 CA $2,305 per person May 13 - May 16 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Charlottesville (CHO) 9/10 Wonderful! (8 reviews) Great room. Convenient. Reviewed on Nov 29, 2025 ## 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! (10 reviews) We had a great experience! The host was extremely responsive and the house was amazing. We loved the hot tub, the views and that the house had everything we needed plus more. We even had an issue on my end that we had to very last minute add a pet that they were understanding about. Would definitely ... Reviewed on Mar 1, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=119318633&PinnedHotelID=119318633&HadPinnedHotel=true®ionId=553248635976481526) [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=119318633&PinnedHotelID=119318633&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! (86 reviews) Della was amazing and allowed for an early check in once the condo was cleaned and ready for us, which was much appreciated after traveling with a toddler. She was very responsive and helpful throughout our stay. Place has everything you need and gorgeous views. The deer even came up to our window ... Reviewed on Apr 6, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=48830715&PinnedHotelID=48830715&HadPinnedHotel=true®ionId=553248635976481526) [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=48830715&PinnedHotelID=48830715&HadPinnedHotel=true®ionId=553248635976481526) ![Hotel 24 South](https://images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel 24 South 24 South Market Street Staunton VA Fully refundableReserve now, pay when you stay CA $159 CA $178 total May 3 - May 4 includes taxes & fees 9.6/10 Exceptional! (1,108 reviews) Nice hotel. Convenient location easy to walk to downtown restaurants and shops. Free parking. Bathroom could use a fan and a door hook for towels and toiletry bags. We’ve stayed here 3 times Easter weekends when visiting our DD at JMU. Reviewed on Apr 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=1311324&PinnedHotelID=1311324&HadPinnedHotel=true®ionId=553248635976481526) [See all 1,281 properties in Chestnut Springs](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F04%2F2026&endDate=10%2F04%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.