Apartment vacation rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort apartment rentals

Weekly apartment rentals

Superhost
The living area features a leather sofa, a glass coffee table, and a wall-mounted TV. Natural light floods through two windows, enhancing the space. A dining table with four chairs is positioned nearby, and a fireplace adds a cozy touch to the room.
Apartment in Wintergreen Resort

Spacious/WalktoResort&WTGMusicFest/PupFriendly

IvanRating, 5 stars3 weeks ago
Great place. Highly recommended
Top guest favorite
A cozy living area features a navy blue sofa paired with a white coffee table. A red accent chair stands beside a television on a yellow media console. Natural light enters through a window, and air conditioning is discreetly mounted on the wall.
Apartment in Staunton
5 out of 5 average rating, 15 reviews

* King Bedroom * Apartment in Victorian Mansion *

Sarah BrookeRating, 5 stars2 weeks ago
Quite, peaceful apartment on second floor of an 1891 mansion. Great views to the south (trees, hills, 19th-century rooflines). High ceilings, wide-plank wood floors, plaster walls, old windows. Access to main hall of the house, which contains a beautiful staircase and arch. Easy walk to the train station, the American Shakespeare Center, and restaurants and retail along Beverly Street and the Wharf.
A cozy condo is partially visible behind snow-covered trees, with a deck and wooden railing leading to snow-blanketed steps. The scene is enhanced by gentle snowfall, creating a serene winter landscape.
Apartment in Roseland
4.85 out of 5 average rating, 176 reviews

Wintergreen Resort Retreat Private Pool for Guests

CaseyRating, 5 stars28 months ago
We stayed in this condo for a fun ski weekend and were so happy with everything. Great location! We shuttled our ski stuff up to the drop off area for ease with the kids (one of us dropped off the fam and gear and parked the car and walked up in our ski boots- took about 5 min) and we all walked home with our gear at the end of the day. Really convenient being so close to the market for any treats or snacks we wanted. The condo itself was plenty spacious for the 4 of us and had everything we needed. We had a great weekend, thank you!!
Guest favorite
The exterior of the building displays a two-story structure with light brown siding and a front porch adorned with white railings. Windows are visible on both levels, complemented by a small garden and walkway leading up to the entrance.
Apartment in Staunton
4.91 out of 5 average rating, 107 reviews

Walker's dream. Close to downtown.

AmyRating, 5 stars2 weeks ago
Lovely little apartment. Exactly as described. As per the description, the shower is on smaller side but it worked perfectly. Wish we were able to stay longer. Will definitely stay here again if in the area.
The exterior features a two-story home with a welcoming red front door. The entrance is accessible by a wooden staircase, surrounded by a deck and landscaped with trees and fallen leaves. A paved driveway accommodates parking for multiple vehicles.
Apartment in Waynesboro
4.75 out of 5 average rating, 507 reviews

Spacious lower level Airbnb! READ SUMMARY!

MegRating, 5 stars3 weeks ago
This was a great little place! The description was perfectly accurate, plenty of room for all our needs, excellent lighting on the deck path up to the door, wonderful location, great deal.
Guest favorite
A panoramic view of rolling mountains is displayed under a colorful sky during sunrise. Soft clouds hover over the lush green hills, creating a serene landscape. The vast expanse of nature invites tranquility and offers a sense of openness.
Apartment in Wintergreen Resort
5 out of 5 average rating, 5 reviews

Family and dog friendly with views and pools!

HeatherRating, 5 stars2 months ago
My husband and I stayed in this condo for the weekend and it was perfect - exactly like the photos and as described. The views out the windows are beautiful and the balcony overlooking the view is perfect and furnished well. This condo was very intentional - it had everything you would need to make the stay feel like home (stocked kitchen, extra bedding and towels, a smart TV, etc). The condo was very clean. Parking was easy and clear. We do not have kids but there were plenty of toys and books for children which was very nice to see. We had a wonderful stay and would absolutely be back, I would definitely recommend this condo for a clean, comfortable stay in Wintergreen with amazing views!
Top guest favorite
A modern living area is furnished with a sectional sofa and accent chairs, arranged around a circular rug. A flat-screen TV is mounted on the wall, complemented by framed artwork. Ambient lighting is provided by a multi-bulb floor lamp and a ceiling fan adds comfort.
Apartment in Staunton
4.94 out of 5 average rating, 150 reviews

Newly renovated 2BR downtown apartment

AdamRating, 5 stars2 weeks ago
A bit noisy around 8am on Friday, Saturday, and Sunday due to the amazing but very busy bakery downstairs. Also we had some activities from the fire department responding to a call across the street.
A spacious patio is enclosed by wooden railings, featuring several metal chairs with cushioned seats. The view beyond showcases lush greenery, trees, and a gently sloping hillside under a clear blue sky, creating a serene outdoor setting.
Apartment in Wintergreen Resort
4.8 out of 5 average rating, 5 reviews

Eagles Court Ski In/Out Condo

PamelaRating, 5 stars2 weeks ago
This is a great spot, you can walk to everything. The owners communicated well. The place is clean and a very nice unit. It is like being in a tree house. We love Eagles!

Private apartment rentals

Guest favorite
A wooden deck is elevated and features a vibrant red umbrella. Surrounding the deck are leafy green plants and a small seating area with pink chairs. A lattice design is present under the deck, adding texture to the space.
Apartment in Lovingston
4.89 out of 5 average rating, 137 reviews

Lovingston Get-Away Lovingston, VA

EmmanuelRating, 5 stars2 weeks ago
Ed and Camille were amazing, they have a sweet apartment with a great Jacuzzi and pool. We were in town for a wedding and were blessed that Ed’s spot was open as it was only 15 minutes from the wedding venue. The apt was clean and everything was working, the kitchen was spotless as well. Ed and Camille were great, very communicative and nice people.
Top guest favorite
An outdoor dining setup on a spacious deck features several plates with a breakfast spread, including eggs, fruit, and pastries. A steaming cup and a glass of juice are present. In the background, a telescope is positioned to enjoy the scenic mountain view under a cloudy sky.
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 31 reviews

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok

AllanRating, 5 stars1 month ago
Spectacular views. The condo was well stocked with anything you may need for a family getaway.
Top guest favorite
A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.
Apartment in Wintergreen Resort
4.98 out of 5 average rating, 84 reviews

Mountain View Nest

AllisonRating, 5 stars5 days ago
This place was easy to find from the parking lot. Hosts gave really easy directions to understand and check in. The most spectacular view and so peaceful, private and quiet. Exactly what I needed for the weekend.
Top guest favorite
A two-story building with a grey facade features large front windows adorned with white trim, showcasing displays inside. Blue shutters frame the windows, and a sign hangs from the front. The structure is situated on a charming downtown street with neighboring brick buildings.
Apartment in Staunton
5 out of 5 average rating, 273 reviews

The Downtown Corner Place - Location and Luxury

MindyRating, 5 stars2 weeks ago
We absolutely loved Martha’s place! Great location, especially being so close to everything. Bed is super comfortable! The best part is how clean the apartment is, it is the cleanest air b&b we have stayed in! Martha has everything you need for your stay, including breakfast! Highly recommend!
Top guest favorite
A balcony is featured, showcasing two Adirondack-style chairs positioned for optimal mountain views. Sunrise illuminates the expansive horizon, with soft light reflecting off the distant landscapes. The floor is made of wood, enhancing the outdoor ambiance.
Apartment in Wintergreen Resort
5 out of 5 average rating, 92 reviews

Endless Mountain Top Views from All The Way Up!

AbbieRating, 5 stars1 week ago
Loved our stay here. Loved it. The view was incredible! The home was clean and cozy. It will be one of my favorite stays that Ive had. And Frost and Fire across the street had the most amazing pizza and pastries, as an added bonus.
Guest favorite
A Gothic Revival Victorian home from 1877 is surrounded by lush greenery, featuring symmetrical hedges. The two-story house has a gray exterior with decorative rooflines and multiple gabled peaks, complemented by a broad set of steps leading toward the entrance.
Apartment in Staunton
4.98 out of 5 average rating, 252 reviews

Updated Victorian Welcomes You & Your Pets

DeanRating, 5 stars1 month ago
Great getaway! Peaceful neighborhood literally a 5 minute walk through a park and over the historic railroad bridge to the shops and restaurants in downtown Staunton. Kitchen was well stocked and the place is decorated with cleaver and eclectic decor. Beautiful historic building with updated/newly renovated interior amenities. Shea was helpful, very accommodating and responsive. Can’t say enough about how nice our stay was - and we’ll definitely be back! Oh yeah - hiking in the mountains was one of our reasons for coming to the area - and the entrance to Skyline Drive is like 15 minutes away. It was the perfect spot for our birthday get away!
Top guest favorite
A cozy living area features a stone fireplace with a wooden mantle. Natural light enters through large windows framed by light curtains. Comfortable seating includes a brown sofa with decorative pillows and a stylish orange chair. An adjacent dining table offers space for meals.
Apartment in Wintergreen Resort
5 out of 5 average rating, 11 reviews

3 Ridges 3 min walk to slopes,besides inn,King bed

AlexusRating, 5 stars2 weeks ago
Great stay! The place was super clean and easy to get into. A perfect spot for a week in mountain getaway. The host was super responsive and friendly. I highly recommend this stay!
Top guest favorite
The exterior of a historic two-story brick house is displayed, featuring white columns and large windows. Lush greenery and colorful flowers surround the front porch, which is complemented by a welcoming atmosphere created by its classic design. The house is set against a clear sky.
Apartment in Staunton
4.98 out of 5 average rating, 321 reviews

the apARTment on Church

AnnRating, 5 stars3 weeks ago
We loved our stay in Staunton. The apartment was comfortable, clean and beautifully decorated!! It was a great place to hang out when not exploring the town!! Thanks for the great hospitality!

Family-friendly apartment rentals

Top guest favorite
A spacious living area features comfortable seating arrangements that include a sofa and armchairs. A traditional rug covers the wooden floor. A brick fireplace serves as a focal point, while soft lighting enhances the inviting atmosphere. A mirrored cabinet reflects the room's details.
Apartment in Staunton
4.94 out of 5 average rating, 387 reviews

The Attic in Restored Mansion Walk everywhere!

NancyRating, 5 stars1 week ago
Ellen’s apartment is a fantastic place to stay for a visit to Staunton. Be aware there are 52 stairs (per Ellen herself) to get up to the apartment, but there was an elevator to help with luggage for the first two floors. It kept us in shape after all the eating we did, but may be a consideration for folks with more limited mobility. The apartment is spacious with lovely decor and great views, even from the (huge) bathroom. The outdoor deck shouldn’t be missed.
Superhost
A spacious studio features a queen-sized bed with crisp white linens and decorative blue pillows. Natural light filters through sheer curtains, illuminating the room. A small artwork in blue hangs above the bed, complemented by bedside lamps. A minimalist table is positioned at the foot of the bed.
Apartment in Afton
4.77 out of 5 average rating, 832 reviews

Studio Apt. in Wine/Brewery Country/on 151

AndreaRating, 5 stars1 day ago
Easy to find location using the directions provided. Self check-in lock easy to operate. Nice and clean location with rocking chairs outside you can sit and look at the amazing views.
The living area features a comfortable sectional sofa, accent chairs, and a coffee table. Natural light enters through a large window adorned with sheer curtains. A flat-screen TV is mounted on the wall, and hardwood flooring adds warmth to the space.
Apartment in Waynesboro
4.3 out of 5 average rating, 177 reviews

Minutes to BC Brewery BR Parkway 151 Wintergreen

PamelaRating, 5 stars1 month ago
We stayed at here last year and were pleased with the location and amenities. When we found new hiking adventures we decided we should stay in the same place. It was perfect for what we needed and the hosts are always helpful and responsive.
Guest favorite
The exterior view of a two-story condo showcases a blend of brown and white siding, with large windows allowing natural light to enter. A wooden deck with steps leads to the main entrance, surrounded by greenery and a gravel pathway.
Apartment in Roseland
4.88 out of 5 average rating, 68 reviews

Close to Activities/Shops/slopeside

WilliamRating, 5 stars4 months ago
Jeffery's condo was perfect for our family's short trip to Wintergreen. The interior setup was comfortable and the location was right off the slopes with great views. The weather was excellent and we wished we had the time to stay longer. We will definitely try to book another stay here next year. Thank you for allowing us to use your wonderful place for our trip!
The multi-story building is nestled among trees, featuring a set of wooden stairs leading to the entrance. Large windows are visible on each floor, allowing natural light to penetrate. A directory sign with multiple unit numbers is displayed at the base of the steps.
Apartment in Roseland
4.82 out of 5 average rating, 235 reviews

Spacious 2 bedroom, 2 bath condo w/ full kitchen

SusanRating, 5 stars6 months ago
Great stay. Not updated, but extremely comfortable. Bed was great! We really enjoyed the fireplace. Everything we needed for a short stay. Small suggestion… get rid of the cable and tv and buy a smart tv for streaming. Thanks for a great stay and for allowing us a later checkout. Much appreciated.
Superhost
The cozy sleeping area features a warm orange wall and rustic wooden furnishings. A spacious bed with a neutral cover is complemented by a patterned rug. A small desk and chair are present, along with a lamp providing soft light, enhancing the serene atmosphere.
Apartment in Afton
4.77 out of 5 average rating, 97 reviews

Earth Room Suite at Galleywinter Farm

ElizabethRating, 5 stars6 months ago
It was really great for our family to get away for a few days over Thanksgiving! The property is beautiful and peaceful, and the suite was cozy. Overall we enjoyed the flexibility of having a few different rooms, being able to cook (as much as we needed/wanted to), and the fact that the earth room doesn't have windows allowed us to sleep in late. As far as amenities, the tub pretty amazing. I also really enjoyed peeking at some of the crafting books on the bookshelves - the cowgirl room in particular has a workshop feel that I enjoyed! Really grateful we were able to go on this trip - thank you!

Quick stats about apartment rentals in Wintergreen Resort

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore