A mountainous landscape with lush green hills and a clear blue sky with contrails.

Wintergreen Vacation Rentals

Q: What are some of the best vacation rentals that Wintergreen has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails : Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 and Remodeled 3BR/2BA Ski Chalet off Tyro Slope .

Where to?

Dates

November 2026

December 2026

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Our top choices for Wintergreen vacation rentals

A spacious living area with a wooden staircase, a dining table, and a sofa.

1. Blackwood Chalet

Nellysford

Patrick

$376 nightly

Nov 9 - Nov 10

Total with taxes and fees

A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

2. Three Little Bears

Nellysford

$280 nightly

Nov 8 - Nov 9

Total with taxes and fees

A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

3. Panoramic Peak

Nellysford

Carrie

$265 nightly

Nov 24 - Nov 25

Total with taxes and fees

A two-story cabin with a balcony, surrounded by trees.

4. Blackrock Canopy

Nellysford

$683 nightly

Nov 17 - Nov 18

Total with taxes and fees

5. Firefly on The Ridge

Nellysford

$338 nightly

Nov 24 - Nov 25

Total with taxes and fees

A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

6. Mountain View Vista

Nellysford

$266 nightly

Nov 15 - Nov 16

Total with taxes and fees

A two-story stone house with a deck, outdoor seating, and a fireplace.

7. Red White and Wintergreen

Pedlars Edge

A hot tub with a wooden deck and a view of a forest.

8. Bear Tracks Cottage

Nellysford

$397 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden deck with outdoor seating and a fire pit.

9. Mountain Mindset

Laurel Ridge

$499 nightly

Nov 9 - Nov 10

Total with taxes and fees

10. Art & Soul

Nellysford

$700 nightly

Nov 8 - Nov 9

Total with taxes and fees

A two-story house with a deck, large windows, and a garage.

11. Love Ridge Mountain Lodging

Lyndhurst

Josh

$186 nightly

Nov 18 - Nov 19

Total with taxes and fees

A hallway with a wooden staircase, a bench, and a door leading to a balcony.

12. Fore Seasons

Nellysford

Menen

$286 nightly

Nov 9 - Nov 10

Total with taxes and fees

13. Modern Nellysford Getaway on 40 Private Acres!

Nellysford

$579 nightly

Nov 9 - Nov 10

Total with taxes and fees

14. Valley Extended Suites

Fishersville

Jamie

$114 nightly

Nov 8 - Nov 9

Total with taxes and fees

An outdoor seating area with a fire pit, wicker chairs, and a view of the landscape.

15. Afton Mountain Vineyards

Afton

Jennifer

$405 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden deck with wicker furniture, a brick wall, and a view of greenery.

16. Bluebird Cottage

Roseland

$261 nightly

Nov 15 - Nov 16

Total with taxes and fees

A kitchen with green cabinets, a built-in microwave, a coffee maker, and a stove.

17. Enjoy Staunton in the Heart of Shenandoah Valley

Staunton

$415 nightly

Nov 8 - Nov 9

Total with taxes and fees

A cabin with a porch, surrounded by trees.

18. Nelson Cozy Cabin

Nellysford

$399 nightly

Nov 9 - Nov 10

Total with taxes and fees

A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

19. Tucked Inn: Lower Unit

Nellysford

$268 nightly

Nov 17 - Nov 18

Total with taxes and fees

A fire pit with chairs, a small house with stairs, and trees in a yard.

20. Artisan's Cottage

Afton

$266 nightly

Nov 9 - Nov 10

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Top Wintergreen Hotel Reviews

Love Ridge Mountain Lodging

Lyndhurst

10/10 Excellent

Darian

A backyard with a swimming pool, lounge chairs, and umbrellas.

Afton Mountain Inn

Afton

10/10 Excellent

Gibson

A wooden porch with two rocking chairs and a white fence.

The Farmhouse at Veritas

Afton

10/10 Excellent

Carlos

A Best Western Plus hotel with a covered entrance, multiple floors, and a landscaped area with trees.

Best Western Plus Waynesboro Inn & Suites Conference Center

Waynesboro

10/10 Excellent

Brandon

A spacious lobby with multiple seating areas, a grand piano, and a reception desk.

Hotel 24 South

Staunton

10/10 Excellent

The only thing I can say about the hotel is that it would be better if they did not charge for the breakfast. The breakfast was great, but with so many other hotels offering breakfast it just seemed a bit much to have to pay for the meal. The wait staff in the dining area was great, but with it being a buffet, I felt like there were too many staff members there. Other than this, the hotel is wonderful!!!!!

Ann

An outdoor patio with a fire pit, wicker furniture, and a brick building with large windows.

Residence Inn Marriott Waynesboro

Waynesboro

10/10 Excellent

Kimberly

A reception desk with a 'Sleep Inn' sign, a 'Welcome!' sign, a 'Manager On Duty' sign, a 'Check Out' sign, and a 'Check In' sign.

Sleep Inn Staunton

Staunton

10/10 Excellent

Anonymous traveler

A grand staircase with white railings and a chandelier, leading to a door with potted plants.

The Blackburn Inn and Conference Center

Staunton

10/10 Excellent

John

A large house with a spacious lawn, a driveway, and a view of rolling hills.

The Crossroads Inn

North Garden

10/10 Excellent

Patty

A spacious living room with a stone fireplace, large windows, and a high ceiling.

Iris Inn and Cabins

Waynesboro

10/10 Excellent

Rachel

A balcony with a table set for a meal, two chairs, and a scenic view of a vineyard.

Woodville Bed and Breakfast

Esmont

10/10 Excellent

Juliana

A spacious living room with a stone fireplace, wooden ceiling beams, and a dining area with brown chairs.

Batten Green Venue & Lodging

Staunton

10/10 Excellent

Wingate by Wyndham Waynesboro

Waynesboro

10/10 Excellent

CHRISTINA

A dimly lit room with a bar area, two armchairs, and a small round table.

Gibson's Warehouse

Staunton

10/10 Excellent

We were very pleasantly surprised and impressed. They have done a spectacular job of restoring and decorating. All appointments and furnishings are upscale and first class. Everything is very modern and new. The location is in the middle of downtown and sits atop a very popular Bistro. The parking lot behind them hosts a farmers market every Saturday. Regarding the farmers market and lot. We parked there on Friday when we arrived. We woke up Saturday to see our 5-day old car gone. It was...

George

Find out more about Wintergreen

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wintergreen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wintergreen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $230 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

What are some of the best vacation rentals that Wintergreen has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 and Remodeled 3BR/2BA Ski Chalet off Tyro Slope.

How many vacation rentals are there in Wintergreen?

Choose from 232 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While you're exploring the area, George Washington National Forest and Humpback Rocks are a couple of picturesque spots to get outside and enjoy nature. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

What’s a vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.

Wintergreen Vacation Rentals

Bundle & Save

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Upfront pricing

Check prices for these dates

Our top choices for Wintergreen vacation rentals

1. Blackwood Chalet

2. Three Little Bears

3. Panoramic Peak

4. Blackrock Canopy

5. Firefly on The Ridge

6. Mountain View Vista

7. Red White and Wintergreen

8. Bear Tracks Cottage

9. Mountain Mindset

10. Art & Soul

11. Love Ridge Mountain Lodging

12. Fore Seasons

13. Modern Nellysford Getaway on 40 Private Acres!

14. Valley Extended Suites

15. Afton Mountain Vineyards

16. Bluebird Cottage

17. Enjoy Staunton in the Heart of Shenandoah Valley

18. Nelson Cozy Cabin

19. Tucked Inn: Lower Unit

20. Artisan's Cottage

Find vacation rentals that suit your style

Top Wintergreen Hotel Reviews

Love Ridge Mountain Lodging

10/10 Excellent

Find out more about Wintergreen

Everything you need to know about Wintergreen vacation rentals

Wintergreen vacation rentals: An excellent choice for every season

How to find incredible deals on Wintergreen rentals

Frequently Asked Questions

Can I find vacation rentals in Wintergreen?

What are some of the best vacation rentals that Wintergreen has to offer?

How many vacation rentals are there in Wintergreen?

What can I see and do in Wintergreen?

What’s a vacation rental in Wintergreen like?

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