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Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Photo gallery for Hilltop Hideaway - Wintergreen 5BR with Hot Tub

A hot tub on a wooden deck with outdoor seating and a view of trees. - Hilltop Hideaway - Wintergreen 5BR with Hot Tub (Wintergreen Resort)
Property video
A spacious living room with a large brown leather sofa, a coffee table, and a dining area with a chandelier. - Hilltop Hideaway - Wintergreen 5BR with Hot Tub (Wintergreen Resort)
A spacious living area with large windows, a dining table set for six, and a wooden staircase. - Hilltop Hideaway - Wintergreen 5BR with Hot Tub (Wintergreen Resort)
A spacious interior with a wooden staircase, a dining area, and large windows offering a view of trees. - Hilltop Hideaway - Wintergreen 5BR with Hot Tub (Wintergreen Resort)
Near Wintergreen Resort, Hilltop Hideaway - Wintergreen 5BR with Hot Tub provides a firepit, an arcade/games room and laundry facilities. For some rest and relaxation, visit the hot tub. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

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About this property

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

  • Welcome to Hilltop Hideaway! Located in the heart of Wintergreen, Hilltop Hideaway features a hot tub, 2 propane firepits with seating, and covered outdoor dining. Inside, you'll love the soaring ceiling with a light-drenched open concept living room / dining / kitchen, plus a separate living room / game room downstairs. With 5 bedrooms, the house sleeps 12 comfortably. Zero steps to enter the home. Plus, pet friendly! Managed by Chris at New School Hosting.

    Hilltop Hideaway is located in the heart of beautiful Wintergreen in Virginia, which has tons to do for all ages, year-round. We are just a few minutes’ drive to the slopes and all the dining and entertainment at Wintergreen. Some of the best hiking trails in the state are off the Blue Ridge Parkway (15 minutes from the home), plus there are other great trails just down the street. Also nearby are two sandy-beach-entrance lakes plus a community pool for swimming, and over dozen wineries, breweries, and distilleries- all within a 30 minute drive.

    The house has 5 bedrooms and 3 bathrooms, with the layout as follows:

    Main level (note: zero steps required to enter home from driveway):

    - Main level deck features covered dining for 6, propane firepit with 4 adirondack chairs, and gas grill (propane provided for firepit and grill)
    - Living room with wood-burning fireplace (wood provided) and big screen smart TV
    - Dining area for 8, plus room for 4 more at the kitchen bar
    - Fully stocked kitchen with brand new counters, stainless appliances, island with bar seating
    - BR1: King bedroom with workspace area and bathroom access
    - Full bath with dual entry (BR1 and hallway)- double vanity and shower/tub combo
    - Laundry room with washer / dryer

    Upper level:

    - Loft area overlooking living room with desk
    - BR2: King bedroom with workspace area
    - BR3: Small bedroom with sofa bed and smart TV
    - Full hall bath with shower

    Lower level:

    - Lower level deck features hot tub and propane firepit with seating for 8
    - Additional living room / game room with pool table, shuffleboard, arcade machine, large smart TV, and multiple seating areas
    - BR4: Queen bedroom
    - BR5: Bunk bedroom with twin-over-full bunk bed plus twin-over-twin bunk bed, and smart TV
    - Full hall bath with shower/tub combo
    - Laundry room with full size washer and dryer

    Other things to note:

    - Hilltop Hideaway is pet friendly! We allow up to 2 dogs with a $100 pet fee (total, not per pet or per night).
    - Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more.
    - Motorcycles are not permitted at Wintergreen Resort
    - The driveway can easily fit 5-6 vehicles. There is an overflow parking lot nearby if needed.
    - Wifi is fast with a strong signal throughout the house and decks.
    - The living room, downstairs living room/game room, and 2 of the bedrooms have smart TVs where you can access whatever streaming services you subscribe to. We do not subscribe to cable.
    - We provide a fully stocked coffee bar with multiple coffee drip and Keurig options
    - Linens and towels provided
    - Guests can enjoy free community pool access in the summer season (though the HOA rules stipulate no more than 6 guests at a time, and the permitted hours are 2-6pm).
    - Pack n play, high chair, and kid dishes provided
    - We do require a separate rental agreement, which we will send a link to e-sign after you book. There are no additional fees beyond those listed here.

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About the area

Wintergreen is home to this holiday home. Zeus Digital Theater and Wayne Theatre are cultural highlights, and some of the area's activities can be experienced at Wintergreen Resort and Sherando Lake Recreation Area. Travelling with kids? Consider Wildlife Center of Virginia and Shenandoah Valley Art Center. Visit our Wintergreen travel guide
View more Holiday homes in Wintergreen
Map
Wintergreen Resort, VA

What's nearby

  • A mountainous landscape with dense green forests and rocky outcrops.
    George Washington National Forest
    1 min walk - 0.0 km
  • A waterfall in a forest with autumn leaves.
    Wintergreen Resort
    3 min walk - 0.3 km
  • A lone tree on rocky terrain with a mountainous landscape in the background.
    Raven's Roost Overlook
    6 min drive - 3.8 km
  • A classical building with a dome, surrounded by lush green trees and a well-maintained lawn.
    University of Virginia
    56 min drive - 77.3 km
  • Bold Rock Hard Cider Nellysford Cidery
    21 min drive - 22.1 km

Getting around

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

Restaurants

  • Belties
    20 min drive
  • Devils Backbone Brewing Company
    16 min drive
  • Iron & Ale At Wintergreen Resort
    23 min drive
  • Margarita's The Flavor of Mexican
    20 min drive
  • The Edge
    6 min drive

Frequently asked questions

Does Hilltop Hideaway - Wintergreen 5BR with Hot Tub have a pool?

Yes, this property has a pool.

Is Hilltop Hideaway - Wintergreen 5BR with Hot Tub pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Hilltop Hideaway - Wintergreen 5BR with Hot Tub?

On-site parking is available at the property.

What time is check-in at Hilltop Hideaway - Wintergreen 5BR with Hot Tub?

Check-in begins at 4:00 PM.

What time is check-out at Hilltop Hideaway - Wintergreen 5BR with Hot Tub?

Checkout is at 10:00 AM.

Where is Hilltop Hideaway - Wintergreen 5BR with Hot Tub located?

This family-friendly Wintergreen holiday home is steps away from George Washington National Forest and Wintergreen Resort. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 miles (15 km).

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Reviews

Hilltop Hideaway - Wintergreen 5BR with Hot Tub Reviews

10

Exceptional

10

Cleanliness

10

Location

10

Property conditions & facilities
Rating 10 - Excellent. 8 out of 8 reviews
Rating 8 - Good. 0 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Beautiful home, very comfortable and close to the rest of Wintergreen.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was exactly as pictured and the hosts were very responsive both before and during our trip. The house was warm, cozy and full of small touches carefully selected to make our stay enjoyable. From special towels for the hot tub and cozy blankets on the couch, we loved all the extra amenities that made Hilltop Hideaway feel special. One of the best perks were the supplies we didn't have to bring along - paper towels, coffee pods, hand soap, laundry & dishwasher detergent - the showers were even stocked with body wash and shampoo/conditioner. It made packing and preparing for the trip a lot easier and gave us more time to relax. The kids snowboarded for two days - just a short 5 minute drive to the resort. The adults loved the fireplaces (inside and out) and the incredible views from all the windows. We would definitely love to come back again. The perfect start to our new year!
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for a family vacation. Very clean and comfortable stay.
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was wonderful, the host was incredible and very responsive. I would for sure recommend this to a friend.
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a lovely, spacious, clean, and comfortable home in the mountains! Hilltop Hideaway has a well-stocked and equipped kitchen, bedrooms with comfortable beds, bathrooms that had plenty of shampoo, conditioner, body wash, etc., a terrific game room that kept the kids entertained, and an overall setting that was perfect for a fun, relaxing New Year’s Eve weekend. Our host, Mary, was extremely responsive. We loved every bit of our stay!
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
We had an absolutely fantastic stay at Hilltop Hideaway in Wintergreen Resort. From the moment we arrived, it was clear this property is something special. The home is beautifully maintained, exceptionally clean, and thoughtfully designed for both comfort and relaxation. Every detail feels intentional—from the cozy living spaces to the well-appointed kitchen—making it easy to settle in and immediately feel at home. The views are stunning and truly elevate the entire experience, especially in the mornings and evenings. What really sets Hilltop Hideaway apart is how seamless and stress-free the stay feels. Everything you could need is already there, and the layout works perfectly whether you're looking for a quiet getaway or time with family. It strikes that rare balance of feeling like a luxury retreat while still being warm and inviting. The location within Wintergreen Resort is ideal—peaceful and private, yet close to everything the resort has to offer. It made for the perfect base to relax, explore, and unwind. This was one of those stays where everything just exceeded expectations. We would absolutely return and highly recommend Hilltop Hideaway to anyone looking for a top-tier Wintergreen experience.
Stayed 4 nights in Apr 2026