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Condo

Where the Trail Ends

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 living room with a grey sofa, a wooden coffee table, a fireplace, and a TV mounted on the wall.
A modern living room with a fireplace, a mounted TV, and a cozy seating area.
A wooden coffee table with playing cards and a lantern in a living room.
A sofa with a 'Welcome' pillow and a patterned throw blanket.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Explore, experience, enjoy
    Guests like the location for activities and attractions nearby.
  • Discover nearby landmarks
    Walk to Wintergreen Resort
1 bedroom1 bathroomSleeps 6

Popular amenities

  • Swimming pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony or patio

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
    ‪56 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪62 min drive‬

Rooms & beds

1 bedroom (sleeps 6)

Bedroom 1

1 Queen Bed

Common area 1

1 Double Futon

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen

About this property

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.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 2759670vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Wintergreen

Located in Wintergreen, this condo is in the mountains. Shenandoah National Park and Rockfish Gap Entrance Shenandoah reflect the area's natural beauty and area attractions include Wildlife Center of Virginia and War Fields.
Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 km
  • Bold Rock Hard Cider Nellysford Cidery - 17 min drive - 18.7 km
  • Rockfish Gap Entrance Shenandoah - 36 min drive - 43.9 km
  • University of Virginia - 56 min drive - 79.8 km
  • John Paul Jones Arena - 60 min drive - 81.5 km

Getting around

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

Restaurants

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

Frequently asked questions

Does Where the Trail Ends have a pool?

Yes, this property has a pool.

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

As of 17 Jul 2026, prices found for a 1-night stay for 2 adults at Where the Trail Ends on 31 Jul 2026 start from £210, 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.

Is Where the Trail Ends pet-friendly?

No, pets are not allowed at this property.

How much is parking at Where the Trail Ends?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 11:00 AM.

Where is Where the Trail Ends located?

Situated in the mountains, this condo building is steps away from Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 miles (15 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 52 out of 57 reviews
Rating 8 - Good. 4 out of 57 reviews
Rating 6 - Okay. 1 out of 57 reviews
Rating 4 - Poor. 0 out of 57 reviews
Rating 2 - Terrible. 0 out of 57 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

6/10 Okay

Diana J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice resort
Stayed 2 nights in May 2026
Verified

10/10 Excellent

John L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo was impeccable and located just a short walk away from the pizza/pastry/wine shop. The surroundings in Wintegreen are lovely. We had a very nice, relaxing stay.
Stayed 4 nights in May 2026
Verified

10/10 Excellent

Carrie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My husband and I came for our anniversary. The place was perfect for the two of us. Enjoyed coffee each morning in the little deck. Very clean and we could walk to the Market and dinner. Keith communicated with us each day.
Stayed 2 nights in Jul 2026
Verified

10/10 Excellent

Aline L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice condo. Great location. Clean. Comfortable.
Stayed 1 night in May 2026
Verified

10/10 Excellent

April S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location. Wonderful host. We will be back!
Stayed 1 night in Apr 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

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

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

Caryn U.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Modern Mountain Condo was a great place to gather with friends, play games, watch movies and just relax. There was plenty of room and everything needed for a fun girls' night out.
Stayed 1 night in Apr 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

Amy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our first impression of Where the Trail Ends was excellent! The condo was exactly as described—clean, well-stocked, comfortable, and thoughtfully decorated. My husband and I stayed for two nights and thoroughly enjoyed our visit.During our stay, we hiked Crabtree Falls and explored several local breweries, making for a wonderful getaway. Since we now live in North Carolina, it was especially nice to return to our old stomping grounds and revisit an area we have always enjoyed.We were so pleased with our experience that we're already planning a return trip later this summer. We will definitely try to stay at Where the Trail Ends again and would highly recommend it to anyone looking for a relaxing and convenient place to stay in the area.
Stayed 2 nights in Jun 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

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

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

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

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

About the host

Hosted by Keith Weightman

Host profile image
Welcome to our condo. We hope you enjoy your stay and don't hesitate to reach out should you have any questions!

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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