Condo vacation rentals in Shenandoah

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Popular amenities for Shenandoah condo rentals

Weekly condo rentals

Guest favorite
A broad panoramic view highlights rolling green mountains under a dramatic sky. Various shades of green from the dense foliage contrast with the soft blue tones in the distance, creating a serene natural landscape. The foreground features lush vegetation, enhancing the peaceful atmosphere.
Condo in Wintergreen Resort
4.9 out of 5 average rating, 48 reviews

2 br/2 b condo; skiing; hiking; wineries; pool

JamesRating, 5 stars2 months ago
This was a getaway to see our kids, and it was perfect. Amanda went out of her way to accommodate our needs, and her place is a great refuge. What really stands out is how communicative she was in every step from booking, to questions, checkin, and checkout. Everything went super smoothly and we enjoyed our stay.
Superhost
The Woodstone Recreation Center features a large outdoor play area with green and teal playground equipment. The facade is adorned with holiday wreaths, and a well-maintained grassy space is visible in the foreground. The structure has a distinctive roof design and large glass windows.
Condo in Massanutten
4.84 out of 5 average rating, 25 reviews

Massanutten Woodstone or Summit 4BR, 4BA

HeatherRating, 5 stars3 months ago
Daniel was great and our family of six really enjoyed our stay! It was a great deal and a great time!
Top guest favorite
A living room features a stone fireplace with a wooden mantel. A clock is mounted above, and decorative items are displayed on the mantel. Hardwood flooring complements the room's layout. The space is open to a kitchen area, visible in the background, with light cabinets and appliances.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 87 reviews

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

MackenzieRating, 5 stars4 days ago
The place was super nice, honestly better than the pictures! Our group had a great time and all loved the place. Everything was super clean and organized. There was also a binder with local recommendations and we visited some of those restaurants and they were fantastic. I would definitely stay here again and recommend it to anyone.
Guest favorite
A wooden deck overlooking a calm body of water is shown, featuring two Adirondack chairs positioned to take in the views. The surrounding area is filled with trees showcasing autumn foliage, creating a serene outdoor space.
Condo in Mineral
4.93 out of 5 average rating, 46 reviews

Beautiful waterfront condo w/private boat slip

OmarRating, 5 stars1 week ago
The best vacation spot with a beautify condo! Had a blast at this place and will definitely be coming back for sure. The house the view the furniture, everything about the trip was amazing!!
Guest favorite
An expansive indoor waterpark features various water attractions, including slides and play areas. Shallow pools are surrounded by soft landscaping, while structures for water activities create a vibrant atmosphere. A domed ceiling allows natural light to flood the space, enhancing the lively environment.
Condo in McGaheysville
4.84 out of 5 average rating, 144 reviews

Massanutten Woodstone 2-BR, 2 Bath

OsvaldoRating, 5 stars3 months ago
Andy was very responsive and gave clear instructions. We had been at this resort a few times in the past and the unit we received was very nicely appointed and updated. We had all amenities and were super close to the indoor pool and gym. Comfortable.
Guest favorite
A rustic stone fireplace is adorned with a wooden mantel, decorated with festive greenery and a wreath. Two white stockings hang gracefully, while a gentle fire burns in the fireplace. A small tree and holiday figurines add seasonal touches.
Condo in Mount Jackson
4.89 out of 5 average rating, 74 reviews

Cozy condo at Bryce Resort

PhillRating, 5 stars2 months ago
We were here for a brief weekend getaway to go snowboarding with the family. It was exactly what we were looking for. It was ski in/out with only a 5-6 minute walk to the bunny slope and lifts. The bed was very comfortable.
Guest favorite
A snowy mountain landscape is shown, with a ski lodge in the background. Skiers are seen enjoying the slopes, while trees with glistening ice stand nearby. The sky is clear and blue, highlighting the scenic winter atmosphere.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 86 reviews

Beautiful Mountain Getaway - Walk to Everything!

RachelRating, 5 stars1 month ago
Beautiful and well stocked condo. Perfect location, we could walk to everything on our ski trip. Wonderful and hospitable hosts!
Guest favorite
A covered deck features a round table surrounded by four chairs, providing a shaded space. Trees and greenery are visible beyond the railing, creating a natural setting that enhances the outdoor experience.
Condo in Wintergreen Resort
5 out of 5 average rating, 23 reviews

Wintergreen condo near Nature Foundation & Spa

CourtneyRating, 5 stars2 months ago
We've stayed in a lot of condos in Wintergreen over the years, and this may be one of my favorites. This was a very comfortable two bedroom / two bathroom. It was a perfect size for our group of 2 adults and 2 teens. The furnishings were very nice. It is easy to get into (first floor). The view is of the woods behind the condo and quiet. Also, we appreciate how responsive the host was! She quickly returned our call in the evening when we had a little trouble getting into the lock code. Her instructions had been perfect; we just made a mistake with the code. We should have brought a little dishwashing detergent. There was one pod there. I'd stay there again.

Pet-friendly condo rentals

Top guest favorite
A bright living area features a teal couch adorned with a yellow cushion, complemented by a soft throw blanket. A coffee table sits in front, while a gray armchair is positioned nearby. Natural light pours in from the sliding glass doors, enhancing the space's inviting ambiance.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 126 reviews

Mtn/Firework Views from Private Deck ~ King Suite

AlyssaRating, 5 stars2 weeks ago
My fiance, our dog, and I had a wonderful stay at Susie's! The condo was well stocked with anything you may need during your stay. The dog bowls and towels were a thoughtful addition right as you walked in. The bed was comfortable and we loved having the TV up there to unwind after a day of hiking around nearby trails. We ended up having to reschedule the days that we were coming, and Susie made that process very easy. We will definitely be staying here again next time we come to the area!
Guest favorite
The living area features comfortable leather seating arranged around a wooden coffee table. A fireplace is visible, surrounded by a stone accent, and large windows allow natural light to fill the space, offering views of the outdoors.
Condo in Wintergreen Resort
4.88 out of 5 average rating, 113 reviews

1720 High Ridge at Wintergreen Resort

HuntRating, 5 stars1 month ago
Beautiful location with the daily sunrise over the blue ridge mountains is captivating. Kimberly who manages the property is the provides the best customer service I've ever had at Air B&B . (Got well over 100 nights in withAirB&B)
Guest favorite
A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.
Condo in Wintergreen Resort
4.91 out of 5 average rating, 164 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

MeganRating, 5 stars3 weeks ago
It was a great stay here! It’s in the Wintergreen Resort which was great for hikes with the pups, restaurants within walking distance at the resort, and not too far of a drive to wineries & breweries. Would definitely stay again!
Top guest favorite
Two red adirondack chairs are positioned on a porch, facing a vibrant sunrise over the mountains. A small side table accompanies the chairs, with distant views of rolling hills and valleys visible under a colorful sky.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 228 reviews

Best View in the Blue Ridge from Biscuit's Porch

CassandraRating, 5 stars3 weeks ago
View is even more beautiful in person! We loved the balcony. Kitchen had everything we needed to make meals at home. Our pup loved the place too!
Guest favorite
A balcony view captures rolling green hills beneath a layer of clouds, with distant mountain peaks rising above. A wrought iron dining set is present on the balcony, providing a serene space for enjoying the landscape.
Condo in Wintergreen Resort
4.96 out of 5 average rating, 178 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

TimRating, 5 stars1 month ago
Lindsay’s place was perfect for our family’s ski weekend. The condo was spacious and had everything we needed. The views were amazing! Lindsay was a great communicator and very responsive host. Highly recommend!
Top guest favorite
The entrance to the condo is framed by greenery and features double doors. A small patio with seating is visible, surrounded by fallen leaves, creating a natural and inviting setting.
Condo in Wintergreen Resort
4.94 out of 5 average rating, 246 reviews

Cozy, clean, quiet mountain condo- King bed

ChristieRating, 5 stars4 days ago
Ritta's condo is clean, spacious and comfortable, situated in a woodland sanctuary of peace and quiet. Loved each morning and evening of spacious solitude.
Guest favorite
A modern kitchen is presented with light gray cabinets and new countertops. A dining table for four is positioned beside the kitchen. A cozy blue couch faces a television on a media console, while appliances, including a microwave and coffee maker, are within easy reach.
Condo in Basye
4.82 out of 5 average rating, 28 reviews

Mountain views, peaceful & relaxing, pet friendly

KyrstenRating, 5 stars4 days ago
We had such a lovely stay at this cute mountainside condo! The space was clean, cozy, and had everything we needed for a comfortable and relaxing trip. Doug’s recommendations for local food spots and hiking trails were so helpful!
Guest favorite
A spacious bedroom features a large bed adorned with a plaid blanket, complemented by a cozy faux fur throw draped over a chair. Natural light filters in through a window, illuminating the fireplace and wooden accents in the room.
Condo in Wintergreen Resort
4.92 out of 5 average rating, 60 reviews

Best Panoramic Views with 2 Floors

GinaRating, 5 stars2 months ago
Owners great to work with and very responsive. Place is cozy with beautiful views, ideally located within Wintergreen. Highly recommend!

Condo rentals with a pool

Guest favorite
The exterior of the mountain condo is displayed, featuring a brown wooden structure with a steeply pitched roof. A wooden walkway leads to the entrance, bordered by low greenery. Large windows adorn the upper level, providing natural light. The setting is surrounded by trees, indicating a tranquil environment.
Condo in Wintergreen Resort
4.96 out of 5 average rating, 28 reviews

Pepper's Mountain Pad

KateRating, 5 stars2 months ago
An amazing host that was quick to respond and had great communication. The place was neat and easy and super close to Wintergreen Resort! Would book again!
Guest favorite
A deck features two comfortably arranged chairs with cushions, overlooking expansive views of the Blue Ridge Mountains. Clear skies are visible, and the natural landscape extends into the distance, highlighting the serene outdoor setting.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 19 reviews

Recently updated - view of the Blue Ridge Mtns

JenniferRating, 5 stars3 months ago
This condo was perfect for a long ski weekend for our family of 4. Located close to slopes, clean and with a spectacular view! Would definitely stay again!
Superhost
An indoor pool is featured in a spacious, well-lit area, with large windows providing natural light. Comfortable seating is arranged around the pool, complemented by a clear view of the outdoors. A hot tub is positioned nearby, contributing to the wellness amenities.
Condo in Basye
4.79 out of 5 average rating, 129 reviews

2BR @ Chalet High - Basye, VA

MichaelRating, 5 stars3 weeks ago
The owners of this fine property, have gone the extra mile, to provide an above and beyond resort experience. The ideal location, abundance of amenities and. extras. depending on the season that you choose, this a place you could call home. Waiting for your vacation memories, this chalet is cozy, comfortable, and the perfect mental floss.
Guest favorite
A cozy bedroom features a large bed adorned with a blanket and decorative pillows. A warm wooden accent wall complements the natural light streaming in through large windows. A small table and a plant add to the inviting atmosphere, while a floor lamp provides additional illumination.
Condo in Charlottesville
4.95 out of 5 average rating, 44 reviews

Lovely 2 bed 2 bathroom condo close to UVA

ChristineRating, 5 stars1 week ago
What a charming apartment in a fantastic location. We were close to everything we wanted to do. The apartment itself was so charming, clean, and full of amenities. It was the perfect spot for four moms getting a weekend away! We loved it!
Guest favorite
A comfortable living area is presented, featuring a gray sectional sofa and an ottoman adorned with a decorative pattern. Natural light filters through multiple windows, illuminating the space. A small desk with two chairs is positioned nearby, with a fireplace adding to the cozy ambiance.
Condo in Wintergreen Resort
4.84 out of 5 average rating, 50 reviews

Happy hour on the 18th Hole

KevinRating, 5 stars1 month ago
The place was perfect, we had a group of 4 and it fit us all very comfortably, and it was so nice being very close to the mountain. This is an absolutely fantastic option for those looking to ski/snowboard at Wintergreen and I heavily recommend it.
Superhost
A comfortable living area showcases a stone fireplace surrounded by soft seating. A wooden dining table is visible, complemented by light streaming through the window. Neutral tones enhance the inviting space, while decorative art adds a touch of personality.
Condo in Mount Jackson
4.95 out of 5 average rating, 20 reviews

Bryce Resort - Large Studio with Sleeping Divider

KristenRating, 5 stars4 months ago
Lovely place, nice stay!
Top guest favorite
A well-maintained outdoor pool area is surrounded by greenery and wooden decking. Lounge chairs are positioned around the pool, with a covered structure visible at one end. Sunlight filters through the trees, creating a serene atmosphere for relaxation.
Condo in Wintergreen Resort
5 out of 5 average rating, 39 reviews

The Perch in Wintergreen Laurelwood

BoscoRating, 5 stars1 month ago
We had a wonderful stay at Ashley’s place! The location was perfect for skiing. Ashley was very responsive - we would definitely stay here again!
Guest favorite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 55 reviews

Pool Tennis Golf Hiking Dogs OK Deck Pack ’n Play

EleanorRating, 5 stars2 months ago
Nice condo. Well stocked kitchen. Location is great for both the beginner skier and the more advanced skier. Easy walk to the beginner slope.

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