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.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
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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
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
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
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.
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
Iron & Ale At Wintergreen Resort - 23 min drive
The Edge - 6 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 24 Apr 2026, prices found for a 1-night stay for 2 adults at Hilltop Hideaway - Wintergreen 5BR with Hot Tub on 17 June 2026 start from AU$680, 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 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).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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!
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!