Entire home
Designer Home w/ Incredible Views, Sleeps 16
Family-friendly holiday home with sauna and Hot tub
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Reviews
9.2 out of 10 
Wonderful
6 bedrooms3+ bathroomsSleeps 16
Popular amenities
Explore the area
- Place, Wintergreen Resort
- Place, Raven's Roost Overlook
- Place, Bold Rock Hard Cider Nellysford Cidery
- Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
Rooms & beds
6 bedrooms (sleeps 16)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
2 Single Bunk Beds
Bedroom 5
1 King Bed
Bedroom 6
1 King Bed
Bedroom 7
1 Double Sofa Bed
3 bathrooms, 1 half bathroom
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Bathtub or shower · Toilet
Bathroom 3
Bathtub or shower · Toilet
Bathroom 4
Toilet
Spaces
Deck or patio
Kitchen
Balcony
Dining area
About this property
Designer Home w/ Incredible Views, Sleeps 16
Welcome to Highlands Overlook, a designer-decorated home in the heart of Wintergreen. The deck is second-to-none, complete with hot tub, cedar barrel sauna, fire table, dining for 10, grill, smoker, pizza oven, and views everywhere. The light-drenched interior is equally impressive. With 6 bedrooms plus a private game room with pullout sofa, the home sleeps 16 comfortably. Plus, pet friendly! Managed by Chris at New School Hosting.
There's a ton to do in the area! Highlands Overlook is about a mile to the slopes and a few minutes’ drive to 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). 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 home layout is as follows:
Main level:
(Note: just 1 small step required to enter main level from flat driveway)
- Grand living room with big screen TV
- Dining area for 10, plus room for 4 more at the kitchen bar
- Fully stocked kitchen with granite counters, stainless appliances, and gas range. Dining nook in kitchen features built-in booth seating.
- BR 1: Primary bedroom with king bed. Ensuite bathroom features double vanity and bath/shower combo.
- Game room with pullout sofa, oversized TV, electric fireplace, foosball, shuffleboard, 2 pinball machines, infinity board game table, and additional refrigerator
- Half bath
- Laundry room with full size washer and dryer
- Upper deck features dining table for 10, oversized propane grill, pellet smoker, and pizza oven
Lower level:
- BR 2: King bed with lower deck access
- BR 3: King bed with lower deck access
- Hall bath with shower/tub combo
- Workspace area at end of hallway
- Lower deck features hot tub, barrel sauna, seating area with propane firepit, and multiple places to sit and enjoy the view
Upper level:
- BR 4: King bed with views
- BR 5: King bed
- BR 6: Bunk room with 2 sets of twin-over-twin beds
- Hall bath with shower/tub combo
- Loft area with couch, rocking chair, and incredible views
- Highlands Overlook is pet friendly! We allow up to 4 pets with a $100 pet fee (total, not per pet or per night). We provide some helpful supplies for pet-owners.
- We provide our guests $1500 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 end of our flat gravel driveway can fit 3 vehicles side-by-side, plus another 3-4 vehicles parked single file down the driveway. So if you have 4 or more vehicles, be prepared to have to move cars around some if somebody is blocked in.
- Wifi is fast with a strong signal throughout the house and decks. Four of the six bedrooms, the living room and game room, feature smart TVs where you can access all the main streaming services.
- 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, baby monitor, 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.
There's a ton to do in the area! Highlands Overlook is about a mile to the slopes and a few minutes’ drive to 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). 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 home layout is as follows:
Main level:
(Note: just 1 small step required to enter main level from flat driveway)
- Grand living room with big screen TV
- Dining area for 10, plus room for 4 more at the kitchen bar
- Fully stocked kitchen with granite counters, stainless appliances, and gas range. Dining nook in kitchen features built-in booth seating.
- BR 1: Primary bedroom with king bed. Ensuite bathroom features double vanity and bath/shower combo.
- Game room with pullout sofa, oversized TV, electric fireplace, foosball, shuffleboard, 2 pinball machines, infinity board game table, and additional refrigerator
- Half bath
- Laundry room with full size washer and dryer
- Upper deck features dining table for 10, oversized propane grill, pellet smoker, and pizza oven
Lower level:
- BR 2: King bed with lower deck access
- BR 3: King bed with lower deck access
- Hall bath with shower/tub combo
- Workspace area at end of hallway
- Lower deck features hot tub, barrel sauna, seating area with propane firepit, and multiple places to sit and enjoy the view
Upper level:
- BR 4: King bed with views
- BR 5: King bed
- BR 6: Bunk room with 2 sets of twin-over-twin beds
- Hall bath with shower/tub combo
- Loft area with couch, rocking chair, and incredible views
- Highlands Overlook is pet friendly! We allow up to 4 pets with a $100 pet fee (total, not per pet or per night). We provide some helpful supplies for pet-owners.
- We provide our guests $1500 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 end of our flat gravel driveway can fit 3 vehicles side-by-side, plus another 3-4 vehicles parked single file down the driveway. So if you have 4 or more vehicles, be prepared to have to move cars around some if somebody is blocked in.
- Wifi is fast with a strong signal throughout the house and decks. Four of the six bedrooms, the living room and game room, feature smart TVs where you can access all the main streaming services.
- 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, baby monitor, 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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House Rules
Check in after 4:00 PM 
Minimum age to rent: 25 
Check out before 10:00 AM 
Children
Children allowed: ages 0–17 
Events
No events allowed 
Pets
Pets allowed: limit 4 total 
Smoking
Smoking is not permitted 
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 and a first aid kit 
We should mention
A car is recommended for transport to and from this property
About the area
Roseland
Roseland is home to this holiday home. Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Shenandoah National Park and Rockfish Gap Entrance Shenandoah. Travelling with kids? Consider Wildlife Center of Virginia and War Fields. Take the opportunity to explore the area for water adventures such as swimming. 
Wintergreen Resort, VA
What's nearby
- Wintergreen Resort - 1 min walk - 0.0 km
- Raven's Roost Overlook - 4 min drive - 2.4 km
- Bold Rock Hard Cider Nellysford Cidery - 14 min drive - 15.3 km
- Stoney Creek Golf Course - 20 min drive - 20.1 km
- Sherando Lake Recreation Area - 22 min drive - 13.6 km
Getting around
Restaurants
- Trager Bros Coffee Shop - 22 min drive
- Hill Top Berry Farm & Winery - 21 min drive
- Devils Backbone Brewing Company - 14 min drive
- Belties - 17 min drive
- The Market - 3 min drive
Frequently asked questions
About the host
Hosted by New School Hosting

Premier Host
They consistently provide great experiences for their guests
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