Entire home

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Family-friendly vacation home in Wintergreen with a hot tub

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

Terrace/patio
Lobby
Terrace/patio
Fridge, microwave, oven, stovetop
Dining
Near Wintergreen Resort, Hilltop Hideaway - Wintergreen 5BR with Hot Tub provides a firepit, an arcade/game room, and laundry facilities. For some rest and relaxation, visit the hot tub. Guests can connect to free in-room WiFi.

Entire home

5 bedrooms3 bathrooms

Popular amenities

  • Parking available
  • Hot Tub
  • Pool
  • Dryer
  • Pet friendly
  • Washer

Add dates for prices

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 transportation

  • Wheelchair-accessible parking and van parking available

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • 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.
  • 1 accessible parking space
  • Front entrance ramp
  • Wheelchair-accessible parking
  • Wheelchair-accessible van parking
  • Smoking not allowed

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 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

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

About the neighborhood

Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 3 min walk - 0.2 miles
  • Bold Rock Hard Cider Nellysford Cidery - 13 min drive - 10.4 miles
  • Shenandoah National Park - 18 min drive - 13.7 miles
  • University of Virginia - 37 min drive - 37.8 miles
  • Monticello - 44 min drive - 43.0 miles

Getting around

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

Restaurants

  • ‪Trager Bros Coffee Shop - ‬25 min drive
  • ‪Devils Backbone Brewing Company - ‬16 min drive
  • ‪Hill Top Berry Farm & Winery - ‬24 min drive
  • ‪Belties - ‬20 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.

How much does it cost to stay at Hilltop Hideaway - Wintergreen 5BR with Hot Tub?

As of Nov 27, 2025, prices found for a 1-night stay for 2 adults at Hilltop Hideaway - Wintergreen 5BR with Hot Tub on Dec 17, 2025 start from $525.0, excluding 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 Hilltop Hideaway - Wintergreen 5BR with Hot Tub pet-friendly?

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

How much is parking?

Onsite 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?

Check-out is at 10:00 AM.

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

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

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Hilltop Hideaway - Wintergreen 5BR with Hot Tub Reviews