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Where the Trail Ends

Condo near Wintergreen Resort in Wintergreen

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Photo gallery for Where the Trail Ends

A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.
A wooden coffee table with playing cards and a lantern in a living room.
A cabin with a sloped roof, wooden exterior, and a stack of firewood in front.
A compact kitchen with white cabinets, a black countertop, and two wooden chairs.
A bedroom with a white bed, two bedside tables with lamps, a grey sofa, and a wall-mounted TV.

Reviews

10 out of 10
Exceptional

Entire condo

1 bedroom1 bathroomSleeps 6700 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Wintergreen Resort, VA
  • Place, Wintergreen Resort
    ‪1 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪17 min drive‬
  • Place, University of Virginia
    ‪58 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪62 min drive‬

Room options

About the neighborhood

Wintergreen

In Wintergreen .Within half a mile (1 km) of this Wintergreen condo, you'll find Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead is within 6 miles (10 km) and Raven's Roost Overlook is within 9 miles (15 km).
View more Condo Rentals in WintergreenOpens in a new window

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 miles
  • Bold Rock Hard Cider Nellysford Cidery - 17 min drive - 11.6 miles
  • Rockfish Gap Entrance Shenandoah - 36 min drive - 27.3 miles
  • University of Virginia - 58 min drive - 49.2 miles
  • John Paul Jones Arena - 60 min drive - 50.7 miles

Getting around

  • Staunton Station - 46 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 55 min drive

Restaurants

  • ‪Hill Top Berry Farm & Winery - ‬20 min drive
  • ‪Belties - ‬16 min drive
  • ‪The Edge - ‬4 min walk
  • ‪The Market - ‬2 min walk
  • ‪Devils Backbone Brewing Company - ‬11 min drive

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Where the Trail Ends

Some trips are about doing everything. This one's about slowing down.

Nestled inside Wintergreen Resort, this updated mountain retreat puts hiking trails, ski slopes, wineries, and breweries at your door - then gives you a warm space to come home to. Curl up by the fireplace, cook a real meal in a full kitchen, or take the morning slow on your private patio with mountain views.

When you're ready to explore, everything is close. When you're not, the community pool and quiet will keep you busy.

Similar properties

Exterior
Best Western Plus Waynesboro Inn & Suites Conference Center
Waynesboro
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
4.3 out of 5, Excellent, 1,000 reviews
$95 nightly
The price is $106
Jul 2 - Jul 3
Total with taxes and fees
Best Western Plus Waynesboro Inn & Suites Conference Center

Property amenities

Pool/Spa

  • Communal pool
  • Fenced private pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • Bedroom
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Unit size: 700 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited.

Frequently asked questions

How close is Where the Trail Ends to the airport?

This condo is 41.1 mi (55-min drive) away from the Weyers Cave, VA (SHD-Shenandoah Valley Regional) airport, the closest popular airport to the property.

How much does it cost to stay at Where the Trail Ends?

As of Jun 30, 2026, prices found for a 1-night stay for 2 adults at Where the Trail Ends on Jul 14, 2026 start from $212, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does Where the Trail Ends have an airport shuttle?

Airport shuttle services are not available at this condo.

Does Where the Trail Ends offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Where the Trail Ends?

No, there is no casino at this condo.

What time is check-in at Where the Trail Ends?

Check-in begins at 4:00 PM.

Is there free parking at Where the Trail Ends?

Free parking is not available at this condo.

Does Where the Trail Ends have a pool?

Yes, there's a pool.

Does Where the Trail Ends have a spa?

There are no spa services available at this condo.

How close is Where the Trail Ends to downtown Wintergreen?

This condo is 3.1 mi away from Wintergreen.

Where the Trail Ends Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 51 out of 55 reviews
Rating 8 - Good. 3 out of 55 reviews
Rating 6 - Okay. 1 out of 55 reviews
Rating 4 - Poor. 0 out of 55 reviews
Rating 2 - Terrible. 0 out of 55 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Daniel T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was an amazing cozy place for the weekend. Everything is near by and easy to get to. The kit hen is well stocked for cooking, and the back porch was lovely to sit on.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Meredith T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Dennis M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place for a quick trip with a small to medium sized family!! Plenty of sleeping spots despite only 1BR
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Joyce B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Kim B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was excellent with communication. Our stay was very comfortable!
Stayed 5 nights in Jan 2026
Verified

10/10 Excellent

dorothy c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home that made the perfect mountain ski weekend. The host was great at communicating and made our trip wonderful and stress free!
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Steve W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host communicated well, kept us in the loop. The condo was very comfortable and well appointed and clean.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

George P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location, walked right over to the top of the slopes and about 30 yards from the market. Everything was clean, in good working order and perfect for our party of three
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Susan

Liked: Cleanliness, check-in, communication, listing accuracy
The property was just as described and the communication was a breeze. The view from the unit’s deck was beautiful.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Julie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet, one-night stay while in the area for an event.
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Chris C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice! Great place.
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Mark R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wintergreen resort is outstanding and great for kids. The condo was perfect and centrally located to many fun activities and hiking.
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Ashok G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Ideal location for skiing at Wintergreen.
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Ace B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect. Very welcoming, responsive, and clean.
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Jason L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute rental with stellar heat and hot water! The host was very responsive throughout my trip. I would definitely recommend!
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

Canden L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host is quick to respond. Condo is cozy, quiet and very clean. Bed is super comfortable. Walking distance from Exxon Market, which has really good food options beyond gas station fare. Great getaway even when it's not snowing.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

jackie p.

Liked: Cleanliness, check-in, communication, location, listing accuracy
I have been coming to Wintergreen since 1999 and this is by far the best condo I’ve ever stayed in! Absolutely loved it! So clean, well apportioned, cozy, comfortable, absolutely adorable, and Keith was an extremely responsive, kind host. Can’t wait to book our next trip back to this exceptional condo!
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Amy Sara H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo was lovely and very clean. The host is communicative and helpful, with excellent, simple instructions. It is very convenient being next to the market. We really enjoyed hanging out in the area.
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

trina b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Keith was amazing. He responded in minutes to every question I had. The condo itself was perfect. Across the street from the ski lifts, spotless and every amenity you might need or want for your stay. I can’t say enough about it and plan on going back again very soon!!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Brett D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great little condo for a quick getaway for a wedding. Spent very little time in the unit, but convenient, affordable and very clean!
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Richard H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

Location of place was perfect for the wineries and distilleries we visited
Stayed 1 night in Aug 2024
Verified

10/10 Excellent

Amanda E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great for families

We loved the proximity to the little market store (which we went to several times) and the slopes, as well as the flexible sleeping options for the kids.
Stayed 2 nights in Dec 2024
Verified

10/10 Excellent

Baylee E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place, close to slopes

We had a great stay, the place is a good size for four friends, and the couch bed is super comfortable. Easy walk to skiing, convenient check in, and those host was communicative.
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Joshua F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Overnight ski trip

Comfortable stay for a father son ski trip.
Stayed 1 night in Feb 2025
Verified

10/10 Excellent

Kelsey N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future!
Stayed 1 night in Jul 2025

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