Entire home

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

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

Exterior
Property video
Terrace/patio
Living area
Property grounds

Reviews

10 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 12

Popular amenities

  • Swimming pool
  • Hot tub on site
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine

Explore the area

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

Rooms & beds

5 bedrooms (sleeps 12)

BR1: Main level king

1 King Bed

BR2: Upper level king

1 King Bed

BR3: Upper level sofa bed

1 Double Sofa Bed

BR4: Lower level queen

1 Queen Bed

BR5: Lower level bunk room

2 Single Bunk Beds

3 bathrooms

Lower level full bath

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Main level full bath

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Upper level full bath

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Balcony
Dining area

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.
- 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.
Our prices include all fees. No hidden fees.

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About the area

Wintergreen

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 War Fields.
Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 3 min walk - 0.3 km
  • Bold Rock Hard Cider Nellysford Cidery - 21 min drive - 22.1 km
  • Blue Ridge Parkway North Entrance - 31 min drive - 37.4 km
  • University of Virginia - 59 min drive - 76.6 km
  • John Paul Jones Arena - 64 min drive - 79.0 km

Getting around

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

Restaurants

  • ‪Belties - ‬20 min drive
  • ‪Hill Top Berry Farm & Winery - ‬24 min drive
  • ‪The Edge - ‬6 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬23 min drive
  • ‪The Market - ‬5 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Alyssa C.

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

10/10 Excellent

David R.

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

10/10 Excellent

Adam S.

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

10/10 Excellent

Yvonne G.

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

10/10 Excellent

Susan M.

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
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