Chat n Chill on the Hill - Wintergreen, VA

Chat n Chill on the Hill

Wintergreen Resort, VA, United States
11
4
3.5

About

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! - 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
  • TV
  • Washing Machine
  • 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
  • TV
  • Washing Machine
  • 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

Michelle
April 2026
What a beautiful and peaceful location! The drive up the mountain is curvy and has majestic views along the way. Definitely recommend all wheel drive or four wheel drive for peace of mind. The home is exactly as shown; there is so much space and we appreciated the design. We are already planning on reserving the house again and bringing our friends and family; and definitely in the winter to do some skiing. The owls are amazing in the late evening and early in the morning. We drove to waterfalls and hiked and our little fur baby settled right in. Lovely place and you can tell it is well cared for
Carrie
April 2026
Our family recently stayed at Chat & Chill to celebrate Easter with our family. Upon arrival the house was amazing! We were very pleased! The house was very clean with many amenities. The host was very quick to respond. We did stay an extra night that was added on during our stay that transaction happened with ease. The beds were very comfortable on all three floor floors. The house was very peaceful, relaxing, we all felt like we were at home, and it felt very clean and comfortable to be in. We will most definitely be booking a future stay at chat and chill! Thank you!!!
Carlos Alberto
April 2026
We had an amazing stay at Chat n' Chill on the Hill and couldn’t have asked for a better experience. The property was exactly as described—clean, well-maintained, and very comfortable. The kitchen was incredibly well stocked with more than everything we needed, which made our stay even more enjoyable. The location was perfect for us—quiet, private, and ideal for disconnecting while still being close to great hiking trails. The views, the sense of privacy, and the overall space really made this place special. Communication with the host was excellent—fast, clear, and very helpful throughout our stay. Everything about this trip felt smooth and well thought out, and honestly, the entire experience was a pleasant surprise. It was also a great value for what you get. We highly recommend this place and would absolutely stay here again!
Charlene
March 2026
This is such a beautiful and cozy house! It had everything we wanted! We were able to enjoy coffee on the deck. The entire house was clean! Whenever we had a question, we always received an answer immediately!!! We will definitely be staying at this house again! Thank you for having such a wonderful place for guests to stay!!!!
Sonia
March 2026
We loved our stay! The views out the front windows are breathtaking in the winter. There was plenty to keep our kids happy in the basement, while the adults got to enjoy the peaceful scenery upstairs. It was a quick drive to get to the slopes and a short drive down the mountain to some great restaurants. I’d definitely recommend staying here. The hosts were friendly and helpful.
Laura
January 2026
It's a lovely house right in the Wintergreen resort area. We were a family group with 6 adults and two kids. The layout was great, as there were two different living room places--the main living room and the downstairs play room, which was great for the kids. The one thing to know is that the mattresses are very firm. Five out of six of the adults found them to be too firm for our liking. But, if you like a firm mattress, it would be perfect!
Laura
January 2026
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.

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