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Find Historic Hotels in Wintergreen, VA

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Our top choices for Wintergreen historic hotels

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Hotel 24 South

Hotel 24 South

3.0 star property
Staunton
9.4 out of 10, Exceptional, (1037)
"Super hotel in a super location! Very pleasant stay."
United States
Timothy
$103 nightly
The price is $115
Dec 17 - Dec 18
Total with taxes and fees
Hotel 24 South
Free daily continental breakfast
Econo Lodge Waynesboro - Skyline Drive

Econo Lodge Waynesboro - Skyline Drive

2.0 star property
Waynesboro
7.0 out of 10, Good, (120)
"Needs updated rooms "
United States
Evan
$49 nightly
The price is $55
Jan 10 - Jan 11, 2026
Total with taxes and fees
Econo Lodge Waynesboro - Skyline Drive
Desk, laptop workspace, blackout drapes, iron/ironing board
Quality Inn Waynesboro - Skyline Drive

Quality Inn Waynesboro - Skyline Drive

2.5 star property
Waynesboro
7.0 out of 10, Good, (821)
"It’s an older motel and could use some sprucing up, but the kind and courteous demeanor of the staff makes up for everything! It was a great stay! I would stay here again. "
United States
Samuel
$62 nightly
The price is $69
Dec 16 - Dec 17
Total with taxes and fees
Quality Inn Waynesboro - Skyline Drive
Terrace/patio
High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly

Crozet
9.8 out of 10, Exceptional, (104)
"reaturants walking distance, just wish the water pressure was better"
United States
ann l.
$310 nightly
The price is $333
Dec 11 - Dec 12
Total with taxes and fees
High Street | Walk to Everything Crozet | Pet-Friendly
Exterior detail
Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet

Crozet
10.0 out of 10, Exceptional, (68)
"Communication was excellent, check in easy, the apartment was stocked with all essentials and down right adorable. Will definitely stay again when we are back in the area. "
United States
Mary Lynn W.
$226 nightly
The price is $243
Dec 11 - Dec 12
Total with taxes and fees
Stay in Crozet Train Suite in Downtown Crozet
Outdoor dining
The Barn at Haden near Wineries and C'ville

The Barn at Haden near Wineries and C'ville

Crozet
10.0 out of 10, Exceptional, (124)
"A simply stunning place to stay in! One of the nicest VRBO’s we’ve stayed in. "
United States
Pieter H.
$298 nightly
The price is $341
Dec 14 - Dec 15
Total with taxes and fees
The Barn at Haden near Wineries and C'ville
TV
The Hideaway Suite: Sauna & Lux Amenities

The Hideaway Suite: Sauna & Lux Amenities

Staunton
9.8 out of 10, Exceptional, (19)
"Charming, clean, cozy place. Great location. Would definitely stay there again."
United States
Conchy H.
$304 nightly
The price is $340
Dec 11 - Dec 12
Total with taxes and fees
The Hideaway Suite: Sauna & Lux Amenities
A heated pool
Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries

Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries

Roseland
10.0 out of 10, Exceptional, (33)
"This is a beautiful property full of lots of fun things to do!!The pool is fantastic, the views are amazing, and the house is well equipped to host a big group. Kyle was a very helpful host. He quickly answered all our questions and sent all the house information before we even arrived. We had a great time, and you will too!!"
United States
Will P.
$457 nightly
The price is $504
Dec 11 - Dec 12
Total with taxes and fees
Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries
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

What should a history buff expect from a stay in Wintergreen?
The historical places in Wintergreen are likely a big part of your travel plans. While you're here, you can visit the ski slopes and mountain landscape.
How many historically relevant hotels are there in Wintergreen?
In Wintergreen, you'll find 664 hotels and other lodging options bookable on Expedia though not many historic hotels to choose from.
What are the must-see historical sites and other places to visit in Wintergreen?
Favorite places to visit include Bold Rock Hard Cider Nellysford Cidery, Stoney Creek Golf Course, and Wintergreen Resort. A couple of additional sights to add to your agenda are Raven's Roost Overlook and George Washington National Forest.
What is a historic hotel like in Wintergreen?
Guests who book a historic hotel can sleep someplace that has an officially recognized national historic designation. A castle, a palace or even a pub or an old police station can be considered a historic hotel as long as it's of special interest. Traditional architecture and period features can be admired within the guestrooms or public spaces of historic hotels in Wintergreen, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The building and architecture of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value and how it influenced the community.
Do historic hotels in Wintergreen have modern facilities?
Hotel interiors feature the modern conveniences and safety features you've come to expect, but every effort is made to preserve the historic aspects and traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the popular amenities found in most hotels will also be available in a historic hotel. Rest assured that when you choose a historic hotel in Wintergreen, you won't find a place that's uncomfortable or rundown.

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