Entire home·Private host

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Family-friendly holiday home with Hot tub, steps from Wintergreen Resort

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Terrace/patio - Hilltop Hideaway - Wintergreen 5BR with Hot Tub (Wintergreen Resort)
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Smart TV, fireplace, video games, computer monitors - Hilltop Hideaway - Wintergreen 5BR with Hot Tub (Wintergreen Resort)
Lobby - Hilltop Hideaway - Wintergreen 5BR with Hot Tub (Wintergreen Resort)
Terrace/patio - 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

Entire home

5 bedrooms3 bathrooms

Popular amenities

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

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About this property

Entire place

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

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

New listing- 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. 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).
- We provide our guests $1500 of coverage for accidental damage to the property or its contents. There is no additional cost for this.
- 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.

Property amenities

Pool/Spa

  • Communal pool
  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Wheelchair-accessible parking and van parking available

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Smart TV
  • Video games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Accessible parking space
  • Front entrance ramp
  • Wheelchair-accessible parking
  • Wheelchair-accessible van parking
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Arcade/game room
  • Billiards/pool table

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 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

Rules

Please respect our neighbors! If you are disrespectful / loud and asked to vacate, there will be no refund. Also, quiet hours are from 10PM to 8AM.
No candles, fireworks, or open fires (except at the provided firepit, if applicable)
No refunds due to weather

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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
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

About the area

Wintergreen is home to this holiday home. Zeus Digital Theater and Shenandoah Valley Art Center 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. Visit our Wintergreen travel guide
View more Holiday homes in Wintergreen
Map
Wintergreen Resort, VA

What's nearby

  • Upper Shamokin Falls in the Blue Ridge Mountains, Virginia - Wintergreen Resort, Nellysford
    Wintergreen Resort
    3 min walk - 0.3 km
  • Shenandoah National Park featuring forest scenes and a river or creek as well as a couple
    Shenandoah National Park
    18 min drive - 22.1 km
  • Nighttime view of the Rotunda at the University of Virginia
    University of Virginia
    37 min drive - 60.8 km
  • Monticello featuring a memorial and heritage architecture
    Monticello
    44 min drive - 69.1 km
  • Bold Rock Hard Cider Nellysford Cidery
    13 min drive - 16.7 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
  • Iron & Ale At Wintergreen Resort
    23 min drive
  • Devils Backbone Brewing Company
    16 min drive
  • The Market
    5 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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Hilltop Hideaway - Wintergreen 5BR with Hot Tub Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10

Cleanliness

10

Location

Reviews

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

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

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

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