Chat n Chill on the Hill - Wintergreen, VA

Chat n Chill on the Hill

Wintergreen Resort, VA, United States
11
4
3.5

About

New listing! Welcome to our cozy Wintergreen home, located on one of the most private lots in the area. You'll truly feel at peace with nature on the two levels of decks and seasonal views of the mountains. Sip wine by the two propane firepits or share a meal with outdoor dining for 10. Inside, you'll love the light-drenched living room with a wall of windows that brings the sense of nature inside. Managed by Chris at New School Hosting- check my profile for more reviews. Plus, pet friendly!

Good to know

We have named our home "Chat n Chill on the Hill," because it is the perfect setting to connect with loved ones in a peaceful setting. We are 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 is a great waterfall trail just down the street (see the photo in the listing). 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 4 bedrooms and 3.5 bathrooms, with the layout as follows: Main level: - Main level deck features two propane firepits with ample seating, outdoor dining table that seats 10, and gas grill (propane provided) - Living room with working propane fireplace and big screen smart TV - Dining area for 8, plus room for 4 more at the kitchen bar - Fully stocked kitchen with granite counters, stainless appliances, plus coffee bar (coffee provided) - BR1: Queen master bedroom with ensuite full bathroom - Half bath Upper level: - Loft area overlooking living room with Peleton exercise bike - BR2: King master bedroom with ensuite full bath featuring soaker tub and tile shower Lower level: - Additional living room / game room with pullout sofa, shuffleboard, darts, and arcade game - BR3: Queen bedroom - BR4: Bunk bedroom with queen bed on the bottom, twin on the top - Full hall bath with dual vanities - Laundry room with full size washer and dryer - Lower deck features additional seating Accessibility: - The distance from the parking area to the front door is 26 steps. - You must go up 8 steps to enter the house; there is no step-free entrance. - No bedrooms are accessible without using steps. - There are no grab bars by the toilet or bath. - The main entrance is wider than 32 inches.

Other Details to Note

- We allow one dog (50 lbs max) with a $100 pet fee. Also, the upper deck is entirely enclosed, so they can be outdoors off-leash on the back deck while you enjoy the firepits! - We provide our guests $1,500 of coverage for accidental damage to the property or its contents. The cost of this is already embedded in the cleaning fee. - Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more. - The driveway is flat and can accommodate 3 vehicles without double parking, and 6+ with double parking - Wifi is fast with a strong signal throughout the house and decks. - 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. - Please note that if you would like to send packages to the property, you do so at your own risk. USPS is particularly unreliable. We can not be held responsible for late or undelivered packages. Additionally, we charge $25 for any return services requested, in additional to actual postage.

Availability

What this place offers

Amenities

Common

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

Outdoors

  • Alfresco dining
  • BBQ
  • Fire pit

Entertainment

  • Arcade machine

Common

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

Outdoors

  • Alfresco dining
  • BBQ
  • Fire pit

Entertainment

  • Arcade machine

Kitchen and dining

  • Baking sheet
  • Barbecue utensils
  • Dining table
  • Hot water kettle
  • Oven
  • Refrigerator
  • Toaster
  • Wine glasses

Bathroom

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

Home safety

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

Family

  • Children's tableware
  • Stair gates

Bedroom and laundry

  • Extra pillows and blankets
  • Iron

Heating and cooling

  • Indoor fireplace

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 firepit, if applicable) - No refunds due to bad weather

Accessibility

Neighborhood

Guest Access

Guests have access to the entire home.

Reviews

Laura
January 2026 · Airbnb
The house was absolutely beautiful and our family enjoyed our stay. We loved that it was kid friendly and had gates already in place by stairs and gates on outside deck. The game room was a hit for everyone. We can’t wait to spend another family vacation at this house!! Chris was an excellent host and the online guidebook for the house was very useful.
Lydia
December 2025 · Airbnb
The house was just as described. The host was very communicative and detailed with instructions. My 2 year old and 5 year old loved playing shuffleboard and the arcade game. We hope to make it a tradition to come back yearly!
Sandra
October 2025 · Airbnb
Our family thoroughly enjoyed our stay at Chat and Chill! It is a beautiful house with a beautiful view! The wall of windows in the main living area made a world of difference! Besides letting in so much natural light, we were immersed in the beauty of the autumn leaves. There were also nice views in the main bedrooms. The house was very clean and well maintained. It was beautifully decorated with very nice and comfortable furniture. Since we had a large family, we enjoyed preparing meals to eat at the house. The kitchen was very well stocked with everything you would need! It was also wonderful to be able to all sit together at the large table to eat without being crowded. The outdoor seating area was nice as well with plenty of room for all. The host, Amy, was super responsive to any questions or needs we had which was very nice! I highly recommend Chat and Chill on the Hill!
Timothy
October 2025 · Airbnb
We could not have been happier with our stay. Everything was perfect. If you're looking for a place that all you need to do is pack clothes and show up this is the place. They have everything you need and if you want to pack light take advantage of the full size washer and drier! They are even so pet friendly they provide bowls for your furbabies. Our dog just enjoyed laying and staring out the hugh windows into the trees! Will be back

Find us

Sorry we're unable to show you the location for this property

Approximate location. Full address will be provided on booking.