Find Romantic Hotels in Wintergreen, VA from CA $167

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Check availability on Wintergreen Romantic Hotels

Our top choices for Wintergreen romantic hotels

Property grounds

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (312 reviews)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
The price is CA $141
CA $344 total
includes taxes & fees
Feb 23 - Feb 24
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Exterior detail

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"Cute little place. Well stocked, easy access, and very convenient to wintergreen facilities. "
United States
david
The price is CA $184
CA $401 total
includes taxes & fees
Feb 23 - Feb 24
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Exterior

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes
Wintergreen Resort
10.0 out of 10, Exceptional, (102 reviews)
"Fantastic stay again! Condo is perfect for a get away! "
United States
Jenna M.
The price is CA $227
CA $448 total
includes taxes & fees
Feb 23 - Feb 24
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Interior

You deserve it all! Awesome Views, Comfy Condo & Elevator!

You deserve it all! Awesome Views, Comfy Condo & Elevator!
Chestnut Springs
9.8 out of 10, Exceptional, (203 reviews)
"This unit had the most amazing view! We’ve stayed at Wintergreen many times and this was my favorite!"
United States
lisa W.
The price is CA $239
CA $463 total
includes taxes & fees
Mar 1 - Mar 2
You deserve it all! Awesome Views, Comfy Condo & Elevator!
TV, fireplace, books

Spring Skiing, Aspen Suite — 2 Fireplaces

Spring Skiing, Aspen Suite — 2 Fireplaces
Wintergreen Resort
10.0 out of 10, Exceptional, (75 reviews)
"Stunning views, pet friendly, great walking, good cooking kitchen, well appointed unit. Thank you."
United States
Elizabeth T.
The price is CA $494
CA $990 total
includes taxes & fees
Feb 19 - Feb 20
Spring Skiing, Aspen Suite — 2 Fireplaces
Outdoor spa tub

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Treeloft
10.0 out of 10, Exceptional, (70 reviews)
"Loved our stay - the house, location, and amenities were perfect for us!"
United States
Alex & Kathy N.
The price is CA $546
CA $980 total
includes taxes & fees
Mar 4 - Mar 5
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Smart TV, fireplace, video games, DVD player

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.
Pedlars Edge
9.8 out of 10, Exceptional, (33 reviews)
"The house was great! It was very clean and spacious, and also accessible to older grandparents who use walkers. And the view from the deck is fantastic, particularly with the fall colors. We really enjoyed the activities at Wintergreen, including walking/hiking trails and the riding the chairlift to see fall foliage. We had a great stay! "
United States
Randy S.
The price is CA $430
CA $963 total
includes taxes & fees
Feb 23 - Feb 24
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.
Lobby

Hotel 24 South

Hotel 24 South
3.0 star property
Staunton
9.6 out of 10, Exceptional, (1,088 reviews)
"Easy to park and go to your room, clean rooms, comfortable bed "
United States
ROBERT T PAYNE
The price is CA $150
CA $167 total
includes taxes & fees
Feb 23 - Feb 24
Hotel 24 South
Winery

The Crossroads Inn

The Crossroads Inn
5.0 star property
North Garden
10.0 out of 10, Exceptional, (44 reviews)
"The staff were excellent. Very friendly, great hospitality. We will definitely book again."
United States
Sharon
The Crossroads Inn
Lobby sitting area

Iris Inn and Cabins

Iris Inn and Cabins
4.0 star property
Waynesboro
9.6 out of 10, Exceptional, (9 reviews)
"Incredible Mountain View at Sunset. Extremely comfortable bed. Delicious breakfast."
United States
Dale
The price is CA $456
CA $508 total
includes taxes & fees
Feb 23 - Feb 24
Iris Inn and Cabins
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wintergreen Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Wintergreen?
If you and your partner need a romantic vacation, we'd like to help you plan for it. Our guests also enjoy Wintergreen for its mountain views and skiing. You might consider checking out some of the nearby sights and attractions such as Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course, or Wintergreen Resort. If you're interested in staying close to a particular destination, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Wintergreen?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Wintergreen: The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Wintergreen is 48 inches.
What is there to do in Wintergreen?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all that Wintergreen has to offer. Adventurous pairs will enjoy Wintergreen for its skiing. You might think about visiting Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course, or Wintergreen Resort.
What's the best way to get to Wintergreen and around town during my romantic getaway?
This information about transportation options in Wintergreen might help your romantic trip get off to a smooth start: To get to Wintergreen, book a flight to Weyers Cave, VA (SHD-Shenandoah Valley Regional), which is the closest major airport, located 26.2 mi (42.1 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

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