Hilltop Hideaway - Wintergreen, VA

Hilltop Hideaway

Wintergreen Resort, VA, United States
12
5
3

About

New listing- welcome to Hilltop Hideaway! Located in the heart of Wintergreen, Hilltop Hideaway features a brand new 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. Managed by Chris at New School Hosting- click my profile for more reviews. Plus, pet friendly!

Good to know

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 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/tub combo 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 Details 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.

Availability

What this place offers

Amenities

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Dryer In the building, free or for a fee
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Hot tub
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • Pool Private or Shared
  • TV
  • Washing Machine In the building, free or for a fee
  • Wifi

Outdoors

  • Alfresco dining
  • BBQ
  • Fire pit
  • Outdoor seating
  • Patio

Entertainment

  • Arcade machine
  • Pool table

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Dryer In the building, free or for a fee
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Hot tub
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • Pool Private or Shared
  • TV
  • Washing Machine In the building, free or for a fee
  • Wifi

Outdoors

  • Alfresco dining
  • BBQ
  • Fire pit
  • Outdoor seating
  • Patio

Entertainment

  • Arcade machine
  • Pool table

Kitchen and dining

  • Baking sheet
  • Barbecue utensils
  • Coffee
  • Coffee maker
  • Dining table
  • Dishwasher
  • Freezer
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Wine glasses

Bathroom

  • Bathtub
  • Body soap
  • Conditioner
  • Hot Water
  • Shampoo
  • Shower gel

Bedroom and laundry

  • Bed linens
  • Hangers
  • Iron
  • Clothing storage

Home safety

  • Carbon monoxide detector
  • Fire extinguisher
  • First aid kit
  • Smoke detector

Heating and cooling

  • Ceiling fan
  • Indoor fireplace

Family

  • Children's tableware
  • High chair
  • Travel crib

Parking and facilities

  • Free parking on premises
  • Private living room

Location features

  • Private entrance Separate street or building entrance

House 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 firepits) - No refunds due to bad weather

Accessibility

Neighborhood

Guest Access

Reviews

Tim
February 2026 · Airbnb
Beautifully appointed home, by far the cleanest property that we have ever experienced. Well furnished game room and very enjoyable hot tub. The hosts were excellent in providing information in a timely manner and responsive to any questions that we had during our stay. We look forward to staying at this property again!
Anna
February 2026 · Airbnb
The house was great! We visit Wintergreen every year for some skiing and winter fun, this was our first time at this house and we will definitely be back! It was perfect for our 1 year old and our dogs. We really enjoyed the location; beautiful view and not far from resort! Highly recommend for big families or groups. Hot tub was a plus after being outside in the cold!
Enid
December 2025 · Airbnb
We had a wonderful family stay! The home was cozy yet spacious enough to comfortably accommodate our family of 11 plus our pet. Everything was very clean and well maintained, which made us feel at home right away. Chris was an excellent host—very responsive, helpful, and attentive from start to finish. The instructions were clear, and check-in and check-out were smooth and easy. We truly enjoyed our time here and would absolutely recommend this home to other families looking for a comfortable and welcoming place to stay. Thank you for a great experience!

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Approximate location. Full address will be provided on booking.