Title: Reserve Wintergreen Vacation Packages for 2026 | Expedia.com [Wintergreen Travel Guide](https://expedia.com/Wintergreen.dx10811)[Hotels in Wintergreen](https://expedia.com/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Vacation Rentals in Wintergreen](https://expedia.com/Wintergreen-Vacation-Rentals.d10811.Travel-Guide-VacationRentals)[Flights to Wintergreen](https://expedia.com/Cheap-Flights-To-Wintergreen.d10811.Travel-Guide-Flights)[Things to do in Wintergreen](https://expedia.com/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities)[Car Rentals in Wintergreen](https://expedia.com/Car-Rentals-In-Wintergreen.d10811.Car-Rental-Guide) ![](https://images.trvl-media.com/place/10811/a4bc0982-5dff-46b1-a292-2fab7a458561.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Wintergreen Vacations from $521 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Your Wintergreen Vacation When a break in the city is calling, answer it with a Wintergreen vacation package. The neighborhood of Laurel Ridge, which is good for skiing, adventure sports and mountain biking, makes a fantastic base for your adventures. Fill your days with visits to [Bold Rock Hard Cider Nellysford Cidery](https://www.expedia.com/Bold-Rock-Hard-Cider-Nellysford-Cidery-Nellysford.d553248635974658802.Vacation-Attraction), [Stoney Creek Golf Course](https://www.expedia.com/Stoney-Creek-Golf-Course-Nellysford.d553248621587587057.Vacation-Attraction) and [Hill Top Berry Farm & Winery](https://www.expedia.com/Hill-Top-Berry-Farm-Winery-Nellysford.d553248621532658165.Vacation-Attraction), some of the things you simply have to see during a trip to Wintergreen. Don't delay exploring this city any longer. Your dream Wintergreen vacation is only a few clicks away with Expedia. ## The Latest Wintergreen vacation packages Price found within the past 48 hours. Click for updated prices. ![Holiday Inn Charlottesville-Univ Area by IHG](https://images.trvl-media.com/lodging/1000000/20000/12300/12207/a427b24f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Charlottesville-Univ Area by IHG The Meadows $521 per person Mar 18 - Mar 22 found 1 day ago Roundtrip non-stop flight included Miami (MIA) to Charlottesville (CHO) 8/10 Very Good! (1,004 reviews) Very clean and updated rooms. Reviewed on Feb 14, 2026 ![Little Mod Hotel at the University](https://images.trvl-media.com/lodging/96000000/95560000/95551300/95551238/469a42a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Little Mod Hotel at the University Venable $675 per person Mar 18 - Mar 22 found 1 day ago Roundtrip non-stop flight included Miami (MIA) to Charlottesville (CHO) 9.2/10 Wonderful! (281 reviews) Very kind staff, clean and fun hotel. Great location with lots within walking distance right on UVA Campus. It is about $20 per night for parking at an affiliated garage very close by. They have no vending, but there is a food truck parked out front which seems to have a good menu. It was not open when I visited, so it might be seasonal. Thankfully there are plenty of food options right outside the door. Would stay again! Reviewed on Feb 5, 2026 ![ Oakhurst Inn at the University](https://images.trvl-media.com/lodging/9000000/8060000/8057300/8057244/c8114faf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oakhurst Inn at the University Jefferson Park Avenue $730 per person Mar 18 - Mar 22 found 1 day ago Roundtrip non-stop flight included Miami (MIA) to Charlottesville (CHO) 9.2/10 Wonderful! (517 reviews) Beautiful artistic room and friendly service Reviewed on Feb 14, 2026 ![The Draftsman, Charlottesville, University, Autograph Collection Hotel](https://images.trvl-media.com/lodging/22000000/21500000/21490500/21490417/0d9fbbcb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Draftsman, Charlottesville, University, Autograph Collection Hotel 10th and Page $878 per person Mar 18 - Mar 22 found 1 day ago Roundtrip non-stop flight included Miami (MIA) to Charlottesville (CHO) 9.4/10 Exceptional! (323 reviews) Perfect corner spot! Reviewed on Sep 17, 2025 ![The Doyle Hotel](https://images.trvl-media.com/lodging/47000000/46230000/46221600/46221543/d28782d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Doyle Hotel Starr Hill $656 per person Mar 18 - Mar 22 found 1 day ago Roundtrip non-stop flight included Miami (MIA) to Charlottesville (CHO) 8.6/10 Excellent! (944 reviews) Everything was perfect 5 stars no doubt. Reviewed on Jan 27, 2026 Don't see what you're looking for? See all available trips from Phoenix to Wintergreen [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-15/2026-03-22/?FromAirport=Phoenix,%20Arizona,%20United%20States%20of%20America&Destination=CHO&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_10811) ## Where to stay in Wintergreen Find the best Wintergreen areas and neighborhoods for the activities you enjoy most. [Learn more about Wintergreen](https://expedia.com/Wintergreen.dx10811) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Treeloft When in Treeloft, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area. [Find hotel + flight trips in Treeloft](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Phoenix,%20Phoenix,%20Arizona,%20United%20States%20of%20America&Destination=Treeloft&DestID=553248635976480861&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Pedlars Edge 1 out of top 10 points of interest in this area If you're looking for some top things to see and do in Pedlars Edge and surrounding area, you can visit Wintergreen Resort and Raven's Roost Overlook. [Find hotel + flight trips in Pedlars Edge](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Phoenix,%20Phoenix,%20Arizona,%20United%20States%20of%20America&Destination=Pedlars%20Edge&DestID=553248635976471592&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Chestnut Springs Though Chestnut Springs might not have many top sights, you can venture to the surrounding area to see attractions like Wintergreen Resort and Raven's Roost Overlook. [Find hotel + flight trips in Chestnut Springs](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Phoenix,%20Phoenix,%20Arizona,%20United%20States%20of%20America&Destination=Chestnut%20Springs&DestID=553248635976481526&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Laurel Ridge When in Laurel Ridge, you can plan a visit to Wintergreen Resort and Reids Gap Trailhead, some noteworthy sights in the nearby area. [Find hotel + flight trips in Laurel Ridge](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Phoenix,%20Phoenix,%20Arizona,%20United%20States%20of%20America&Destination=Laurel%20Ridge&DestID=553248635976482248&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Mountain view from Three Ridges overlook along the Blue Ridge Parkway near Wintergreen Resort in west-central Virginia](https://images.trvl-media.com/place/553248635976470298/c5a02e88-ae17-4ab9-9900-f77acc8e7829.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Deer Springs 5/5(3 area reviews) If you're looking for some top things to see and do in Deer Springs and surrounding area, you can visit Wintergreen Resort and Raven's Roost Overlook. [Find hotel + flight trips in Deer Springs](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Phoenix,%20Phoenix,%20Arizona,%20United%20States%20of%20America&Destination=Deer%20Springs&DestID=553248635976470298&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Wintergreen ![Everything is frozen over at Wintergreen Resort. ](https://images.trvl-media.com/place/553248635996625639/07d79deb-5cfc-4068-8e41-c17e7657b695.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wintergreen Resort Hit the slopes in Wintergreen with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area. [](https://expedia.com/Wintergreen-Resort-Pedlars-Edge.d6093285.Vacation-Attraction) #### Bold Rock Hard Cider Nellysford Cidery You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Wintergreen. Discover the mountain views in this family-friendly area, or seek out the ski slopes. [](https://expedia.com/Bold-Rock-Hard-Cider-Nellysford-Cidery-Nellysford.d553248635974658802.Vacation-Attraction) #### Stoney Creek Golf Course Enjoy a round of golf in Wintergreen at Stoney Creek Golf Course. Discover the mountain views and top-notch restaurants in this vibrant area. [](https://expedia.com/Stoney-Creek-Golf-Course-Nellysford.d553248621587587057.Vacation-Attraction) ### What to do in Wintergreen ![Shenandoah Lake](https://mediaim.expedia.com/localexpert/47415968/ffaf144c-664b-4d45-9bf0-3ac119bef216.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Blue Ridge Parkway Virginia Self-Guided Audio Tour $13 per traveler [](https://expedia.com/things-to-do/blue-ridge-parkway-virginia-self-guided-audio-tour.a47415968.activity-details) [See all activities in Wintergreen](https://expedia.com/things-to-do/search?rid=10811) ## Wintergreen Hotel Deals ![2br/2ba: Million Dollar View from Luxury Condo on the Ridge. ](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. Roseland VA $228 nightly $256 total Feb 19 - Feb 20 Total with taxes and fees 9/10 Wonderful! (300 reviews) Excellent view. Great location Reviewed on Jan 21, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=27767679&PinnedHotelID=27767679&HadPinnedHotel=true®ionId=10811) ![The Modern Mountain Condo ](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Modern Mountain Condo Wintergreen Resort VA $215 nightly $242 total Feb 17 - Feb 18 Total with taxes and fees 9.8/10 Exceptional! (42 reviews) Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go! Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F17%2F2026&endDate=2%2F18%2F2026&selected=77096798&PinnedHotelID=77096798&HadPinnedHotel=true®ionId=10811) ![Cozy Cabin with private HOT TUB!](https://images.trvl-media.com/lodging/59000000/58990000/58985800/58985753/90-636eaa8c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Cabin with private HOT TUB! Nellysford VA 10/10 Exceptional! (34 reviews) Charming cabin with a rustic vibe amidst otherwise uninspired housing. Compact yet laid out well with a bonus sleeping loft and en suite master. Enormous hot tub was a highlight on our frigid weekend. Open floor plan for gathering. fireplace, porches, private, trails right outside. Reviewed on Jan 28, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=58985753&PinnedHotelID=58985753&HadPinnedHotel=true®ionId=10811) [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=58985753&PinnedHotelID=58985753&HadPinnedHotel=true®ionId=10811) [See all 671 properties in Wintergreen](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F16%2F2026&endDate=2%2F17%2F2026®ionId=10811) 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. ## Find the Best Wintergreen Vacation Packages ### Things to do near Wintergreen Wintergreen offers an exciting blend of outdoor adventures and sports, making it a perfect vacation spot. Visitors can enjoy skiing on the ski fields, take scenic chairlift rides, or engage in mountain biking. For family-friendly fun, mini golf and disc golf are available. Don't forget to make activity reservations at the resort to fully experience all that Wintergreen has to offer. **Shopping** In Wintergreen, you can shop at local boutiques and gift shops for unique souvenirs. If you're up for a drive, Windmill Square is 13 miles away, offering a variety of shops. Staunton Mall and Orchard Hill Square Shopping Center, both 19 miles away, provide a wider selection for your shopping needs. **Recreation** At [Stoney Creek Golf Course](https://www.expedia.com/Stoney-Creek-Golf-Course-Nellysford.d553248621587587057.Vacation-Attraction), enjoy a round of golf surrounded by scenic landscapes and outdoor vibes, located 1 mile from Wintergreen. For relaxation, head to [Sherando Lake Recreation Area](https://www.expedia.com/Sherando-Lake-Recreation-Area-Lyndhurst.d553248621587527660.Vacation-Attraction), 7 miles away, where you can unwind amidst nature's tranquility. Experience culture and entertainment at [Wayne Theatre](https://www.expedia.com/Wayne-Theatre-Waynesboro.d553248621561864342.Vacation-Attraction), 13 miles from Wintergreen. **Adventure** At [Wintergreen Resort](https://www.expedia.com/Wintergreen-Resort-Pedlars-Edge.d6093285.Vacation-Attraction), enjoy skiing on pristine slopes with breathtaking views, just 3 miles from Wintergreen. For hiking enthusiasts, the [Reids Gap Trailhead](https://www.expedia.com/Reids-Gap-Trailhead-Roseland.d553248621532658159.Vacation-Attraction) offers scenic trails and outdoor adventure, located 5 miles away. Don't miss a visit to [Caromont Farm](https://www.expedia.com/Caromont-Farm-Virginia.d553248635974660506.Vacation-Attraction), 15 miles away, for a unique farm experience. **Nightlife** Wintergreen offers a cozy nightlife with venues like The Edge Restaurant & Lounge, perfect for a relaxed dinner and drinks. For live music and entertainment, check out the nearby Wintergreen Resort. Enjoy the stunning mountain views while sipping cocktails and socializing with friends. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions near Wintergreen Wintergreen, Virginia, is an ideal destination for ski enthusiasts and adventure seekers. Explore a variety of attractions, including ski resorts, museums, and historic houses that offer a blend of culture and outdoor experiences. Whether you’re hitting the slopes or delving into local history, Wintergreen provides plenty of activities for every traveler. Don't miss out on the unique wintergreen attractions that enhance your visit to this charming area. - **[Wintergreen Resort: ](https://www.expedia.com/Wintergreen-Resort-Pedlars-Edge.d6093285.Vacation-Attraction)** Experience the thrill of skiing at Wintergreen Resort, a premier destination just 3 miles away. With its stunning slopes and outdoor adventure vibes, this resort promises fun for all skill levels, making it perfect for families and thrill-seekers alike. - **[Blue Ridge Parkway North Entrance: ](https://www.expedia.com/Blue-Ridge-Parkway-North-Entrance-Afton.d553248633992269464.Vacation-Attraction)** Located 10 miles away, this visitor center welcomes you with outdoor adventure and family-friendly activities. Enjoy breathtaking views and learn about the natural beauty of the Blue Ridge Mountains while soaking up the area's rich history. - **[Raven's Roost Overlook: ](https://www.expedia.com/Ravens-Roost-Overlook-Lyndhurst.d553248621561864282.Vacation-Attraction)** A scenic lookout just 4 miles from Wintergreen, Raven's Roost Overlook offers romantic vistas and adventure vibes. It's an ideal spot for couples to share a moment while taking in the stunning panoramic views of the surrounding landscape. ### Best time to go to Wintergreen The best time to visit Wintergreen is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 33.4°F (0.8°C) | Light Rain | Mostly Sunny | Moderately High | Slightly Low | | February | 37.2°F (2.9°C) | Light Rain | Mostly Sunny | Moderately High | Slightly Low | | March | 44.6°F (7.0°C) | Light Rain | Mostly Sunny | Average | Average | | April | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Average | | May | 64.0°F (17.8°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly High | | June | 72.1°F (22.3°C) | Light Rain | Mostly Sunny | Moderately Low | Average | | July | 76.6°F (24.8°C) | Light Rain | Mostly Sunny | Average | Average | | August | 74.3°F (23.5°C) | Light Rain | Mostly Sunny | Moderately Low | Average | | September | 68.0°F (20.0°C) | Light Rain | Mostly Sunny | Average | Average | | October | 56.8°F (13.8°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 44.8°F (7.1°C) | Light Rain | Mostly Sunny | Average | Slightly High | | December | 38.5°F (3.6°C) | Light Rain | Mostly Sunny | Moderately High | Slightly Low | ### Tips to save on your trip to Wintergreen - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Wintergreen. - Consider traveling to Wintergreen during the low season (December to February) for more affordable options. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Wintergreen Essential Information | Language | English | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Charlottesville-Albemarle Airport (CHO) | | Population | 170 | | Max Temp Winter | 45ºF | | Max Temp Summer | 85ºF | | Top Sights | [Bold Rock Hard Cider Nellysford Cidery](https://www.expedia.com/Bold-Rock-Hard-Cider-Nellysford-Cidery-Nellysford.d553248635974658802.Vacation-Attraction), [Hill Top Berry Farm & Winery](https://www.expedia.com/Hill-Top-Berry-Farm-Winery-Nellysford.d553248621532658165.Vacation-Attraction) and [Stoney Creek Golf Course](https://www.expedia.com/Stoney-Creek-Golf-Course-Nellysford.d553248621587587057.Vacation-Attraction) | ## More vacations you might like ![](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.com/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.com/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) Kid Friendly Vacations 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[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Wintergreen vacation package cost? ### What are the cheapest months to go to Wintergreen? ### How many days is enough for Wintergreen? ### How to find the best Wintergreen package deals? ### Is it cheaper to book a Wintergreen vacation as a package? ### When to book a vacation package to Wintergreen? ### How to plan a trip to Wintergreen? > 1. Choose when to go: Check your diary and get your bags packed. Your favorite season and the activities available will also help you decide when to escape to Wintergreen. > 2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Wintergreen. > 3. Use our [trip planning tool](https://www.expedia.com/why/trip-planning) to discover Wintergreen: Research every part of your trip to Wintergreen with this handy planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings. > 4. Decide how long to go away for: Now that you know more about Wintergreen, you can work out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do. > 5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Wintergreen vacation package. > 6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Wintergreen's best offerings. Find all the exciting [things to do in Wintergreen](https://www.expedia.com/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities) in Wintergreen with our dedicated travel guide. ### Does Expedia offer Book Now, Pay Later Wintergreen vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Bold Rock Hard Cider Nellysford Cidery ](https://www.expedia.com/Bold-Rock-Hard-Cider-Nellysford-Cidery-Hotels.0-l553248635974658802-0.Travel-Guide-Filter-Hotels) - [Hotels near Stoney Creek Golf Course ](https://www.expedia.com/Stoney-Creek-Golf-Course-Hotels.0-l553248621587587057-0.Travel-Guide-Filter-Hotels) - [Nellysford Hotels ](https://www.expedia.com/Nellysford-Hotels.d180913.Travel-Guide-Hotels) - [Cabin Rentals in Nellysford ](https://www.expedia.com/Nellysford-Cabins.d180913-aaCabins.Travel-Guide-Accommodation) - [B&B in Nellysford ](https://www.expedia.com/Nellysford-Bed-And-Breakfast.d180913-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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[Car rentals near Nellysford ](https://www.expedia.com/Car-Rentals-In-Nellysford.d180913.Car-Rental-Guide) - [Car rentals near Wintergreen Resort ](https://www.expedia.com/Car-Rentals-In-Wintergreen-Resort.d6093285.Car-Rental-Guide) - [Van Car Rentals near Wintergreen Resort ](https://www.expedia.com/Van-Car-Rentals-In-Wintergreen-Resort.d6093285-tVan.Car-Rental-Guide-Class) - [Car rentals near Tyro ](https://www.expedia.com/Car-Rentals-In-Tyro.d3000460704.Car-Rental-Guide) - [Car rentals near Sherando ](https://www.expedia.com/Car-Rentals-In-Sherando.d553248634999427295.Car-Rental-Guide) - [Car rentals near Lovingston ](https://www.expedia.com/Car-Rentals-In-Lovingston.d6051822.Car-Rental-Guide) - [Car rentals near Avon ](https://www.expedia.com/Car-Rentals-In-Avon.d553248635975855273.Car-Rental-Guide) - [Car rentals near Faber ](https://www.expedia.com/Car-Rentals-In-Faber.d6353692.Car-Rental-Guide) - [Nellysford Vacation Rentals ](https://www.expedia.com/Nellysford-Vacation-Rentals.d180913.Travel-Guide-VacationRentals) - [Tyro Vacation Rentals ](https://www.expedia.com/Tyro-Vacation-Rentals.d3000460704.Travel-Guide-VacationRentals) - [Faber Vacation Rentals ](https://www.expedia.com/Faber-Vacation-Rentals.d6353692.Travel-Guide-VacationRentals) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app