Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Wintergreen Resort, Virginia
$567 avg/night
Minimum Stay 1 Nights
Bed 5

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Night 1 nights

Min Stay

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 locatedin 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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Kitchen Island Lobster/crab Pot Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Wheelchair-accessible Parking And Van Parking Available
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Firepit Outdoor Furniture
  • POOL/SPA

    Hot Tub Shared/communal Pool
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Computer Monitor Desk Desk Chair
  • LANGS SPOKEN

    English
  • ENTERTAINMENT

    Arcade/game Room Pool Or Billiards Table Video Games Smart TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware Highchair Travel Crib
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces Front Entrance Ramp If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Stair-free Path To Entrance Wheelchair-accessible Parking Wheelchair-accessible Van Parking

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Availability

Review Review

  • Adam S.

    Submitted Jan 30, 2026

    Stayed Jan 16, 2026

    Everything was wonderful, the host was incredible and very responsive. I would for sure recommend this to a friend.

  • David R.

    Submitted Jan 25, 2026

    Stayed Jan 22, 2026

    Perfect for a family vacation. Very clean and comfortable stay.

  • Susan M.

    Submitted Jan 25, 2026

    Stayed Jan 1, 2026

    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!

  • Yvonne G.

    Submitted Jan 2, 2026

    Stayed Dec 28, 2025

    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!

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Total

Includes taxes and fees
$567+
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