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House holiday rentals in Roseland

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Popular amenities for Roseland house rentals

House rentals with a pool

Guest favourite
Home in Roseland
5 out of 5 average rating, 18 reviews

Hot Tub! Wintergreen Resort!

MalenaRating, 5 stars3 days ago
Camille's place at Wintergreen was perfectly situated for our weekend at Devil's Backbone. The house was clean and tidy, it was easy to find, and her directions and instructions for getting there and getting in the house were spot on. it's an adorable little place and has plenty of room with the three bedrooms. We would love to come back and rent again. Our dog loved it too!!
Top Guest favourite
Home in Nellysford
5 out of 5 average rating, 74 reviews

Game Room & Hot Tub Near Wineries + Breweries

EmilyRating, 5 stars1 week ago
Incredible Airbnb across the board! Truly 5 stars! Hope to be back!
Top Guest favourite
Home in Wintergreen Resort
4.88 out of 5 average rating, 136 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

KatieRating, 5 stars3 months ago
We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!
Guest favourite
Home in Afton
4.94 out of 5 average rating, 144 reviews

Farmhouse on Working Vineyard

SarahRating, 5 stars2 weeks ago
We stayed here for a bachelorette weekend and had a great time. The house was even bigger and cozier than I anticipated and the views were gorgeous. We loved being on the same property as Cardinal Point Winery and walked down to do a tasting/enjoy some bottles. The kitchen was stocked with all the tools we could have needed and the pool area was great!
Superhost
Home in Wintergreen Resort
5 out of 5 average rating, 3 reviews

Perfect house

JosephRating, 5 stars3 weeks ago
We had an amazing stay at this beautiful condo in the mountains! The location is perfect for anyone looking to hit the slopes or tour the grounds – making it great destination year round. The condo itself is cozy, clean, and has everything you need for a comfortable stay. The kitchen was well-equipped, which made it easy to cook meals before heading out for the day. The beds were super comfortable, and we slept like babies every night! The host was incredibly helpful, providing us with all the information we needed for the resort, and even sent us local recommendations for dining and things to do in the area. Check-in and check-out were a breeze. Would definitely recommend this place to anyone looking for a relaxing, convenient, and picturesque retreat. We’ll be back next year for sure!
Guest favourite
Home in Wintergreen Resort
5 out of 5 average rating, 23 reviews

Amazing Views | Hot Tub | Mins to Breweries

SarahRating, 5 stars1 month ago
We very much enjoyed our stay, the view from the porch was amazing! Michael was very responsive. The house was well appointed and we loved that there was a Pack n’ Play available for our little one so we didn’t have to pack ours.
Superhost
Home in Schuyler
4.79 out of 5 average rating, 111 reviews

Peaceful Cottage

EvelynRating, 5 stars8 months ago
We stayed at Diana’s place while visiting with our daughter for our annual apple picking trip. Her place was a bit far out away from things, which we expected. It was cozy and had everything we needed for the weekend. I would highly recommend this cozy cottage when you want to get away!
Guest favourite
Home in Roseland
4.91 out of 5 average rating, 81 reviews

Wintergreen Resort: Hike | Swim | Bike | Fish

MarcRating, 5 stars2 weeks ago
Enjoyed our stay. Property was nice. Would consider a future reservation.

Weekly house rentals

Guest favourite
Home in Roseland
4.93 out of 5 average rating, 74 reviews

The Treehouse at Wintergreen

BrandonRating, 5 stars1 month ago
I enjoyed the stay and Beth was a great host! Everything was as described and she was extremely detailed in instructions to make the stay as easy as possible. I would recommend the stay for anyone wanting a mountain getaway or explore the Wintergreen area!
Superhost
Home in Roseland
4.79 out of 5 average rating, 48 reviews

Cozy Country small two bedroom home.

StefanieRating, 5 stars2 weeks ago
My husband and two young kids stayed over the weekend. It was perfect. It was exactly as described. I loved how clean it was and how it had every thing you needed. The location was amazing. We played in creeks, fished, hiked, and stayed up late with family board games. My kids said they didn’t want to leave. Thank you so much for a wonderful stay!!!
Top Guest favourite
Home in Massies Mill
5 out of 5 average rating, 42 reviews

Country retreat w. mountain views + river access

ThomasRating, 5 stars3 days ago
Kelsey’s place was exactly as advertised!! Super clean. Well stocked. Very comfortable. The hot tub and fire pit were awesome. The screen porch was great for morning coffee and watching the deer. We would recommend to everyone and hope to return next year.
Guest favourite
Home in Roseland
4.94 out of 5 average rating, 54 reviews

Farmette! On River by Wintergreen & Blue Ridge Pkw

AmyRating, 5 stars5 months ago
We had a wonderful stay over New Years - convenient to Wintergreen and lots of cool spots to eat. We thoroughly enjoyed the property (the fresh eggs were a bonus) and hostess Amy was very responsive and nice. Thank you for allowing us to stay at such a cool little place - we made wonderful memories there together!
Top Guest favourite
Home in Roseland
4.95 out of 5 average rating, 38 reviews

Gorgeous views, AT access, bike pkwy, breweries

JhonnyRating, 5 stars3 weeks ago
Home as described. Woke up every morning to a beautiful view. A very peaceful and relaxing weekend with my family. Jennifer was very friendly and responsive. Had a great memorial weekend.
Guest favourite
Home in Roseland
4.9 out of 5 average rating, 31 reviews

Mountain retreat with hot tub

NicoleRating, 5 stars1 month ago
Great location easy to find, very beautiful surroundings, never been to Wintergreen before came for just the weekend with girlfriends. Booked a spa package and very close to that location. Ate at the restaurant nearby, mediocre at best. Did a driving tour of the 151 breweries and wineries and had a great time!
Top Guest favourite
Home in Roseland
4.98 out of 5 average rating, 89 reviews

Book for Spring! Nelson 151, MTN views!

LucyRating, 5 stars1 month ago
Katie is the sweetest host ! The place is beautiful all around and so peaceful . Wonderful place to get away from the busy life .
Top Guest favourite
Home in Nellysford
5 out of 5 average rating, 19 reviews

"Glass & Pine" Home close to Bold Rock &Vineyards

SaraRating, 5 stars1 week ago
Lovely place, very clean, stylishly decorated. It is roomy and has a fantastic view. Nice outdoor sitting areas. It is secluded. The only problem my family and I ran into was knowing what driveway to turn in. We failed to see a sign that displayed a house number at the end of the driveway. Other than that the house and our stay was outstanding.

Private house rentals

Guest favourite
Home in Wintergreen Resort
4.89 out of 5 average rating, 28 reviews

Wren Time

MikeRating, 5 stars1 month ago
Great views, great location, nice house, close to wineries and breweries, and responsive host. Overall great stay. Might make this an annual trip!
Guest favourite
Home in Crozet
5 out of 5 average rating, 15 reviews

Orso Blu one-of-a-kind VIEWS in Crozet

JamesRating, 5 stars2 weeks ago
The house is in a beautiful setting surrounded by mountains with peaceful views from the front porch that include a field of lavender and a stream. A forested trail network can be accessed at the far end of the lavender field--so bring your hiking shoes. The house is stunning with clean lines, "european" design and decor that includes high-end appliances and fixtures. Francesca is the ultimate host-very friendly and helpful. She provided all the information and details on the house that you would need for an easy check-in, stay, and check-out. From my initial conversations with her when I booked the house to helpful messages just before and during our stay, I felt like I was staying at the house of an old friend. We look forward to staying at Orso Blu on a future trip!
Top Guest favourite
Home in Afton
4.98 out of 5 average rating, 82 reviews

Mountain View Meadow Cottage

NickRating, 5 stars2 weeks ago
A great get away with a beautiful view so close to so many wineries and breweries!
Guest favourite
Home in Amherst
4.93 out of 5 average rating, 14 reviews

Sweet Country Retreat

CrystalRating, 5 stars1 week ago
Angela was very responsive and went above and beyond to assist us when we requested to extend our stay by a couple of days. The house was very cute, cozy, and clean. The country surroundings very peaceful. The next time we come back to VA we will definitely book with Angela.
Guest favourite
Home in Wintergreen Resort
4.92 out of 5 average rating, 53 reviews

Whispering Creek Hot Tub Pool TennisGolf King Beds

SylviaRating, 5 stars3 weeks ago
We absolutely loved our Memorial Day weekend getaway. The house has everything you need, a well stocked kitchen, comfortable beds & a fantastic deck with a hot tub. The owners were very responsive and helpful and we are already talking about planning a return trip in the Fall.
Top Guest favourite
Home in Wintergreen Resort
4.99 out of 5 average rating, 88 reviews

The Cozy Cottage | Mountain views at Wintergreen

RebeccaRating, 5 stars3 weeks ago
We absolutely love Krista's place - this was our third stay and we can't wait to return. The view is incredible, and it is conveniently located close to the parkway, Wintergreen, parks, and breweries/cideries. Krista is friendly, helpful, and proactive. The open floorplan makes it a great place to hang out with family both indoors and outdoors.
Top Guest favourite
Home in Roseland
5 out of 5 average rating, 37 reviews

Wintergreen Mountain Retreat

RyanRating, 5 stars3 months ago
I stayed at Terri's place with my wife and two friends. The house was spacious, very clean, and had plenty of room for all of us! It is a beautiful home with everything you could need. Highly recommend to anyone looking for a peaceful relaxing getaway!
Guest favourite
Home in Wintergreen Resort
4.89 out of 5 average rating, 66 reviews

Hot Tub EV Charger Mntn View Fireplace Grill Pool

Adou,MRating, 5 stars1 month ago
I was looking for a quiet place in the middle of the nature for our 10 years of marriage anniversary and I think we found the best one. Charlotte was so kind and helpful, she helped me surprised my wife with such a beautiful decoration. We were so impressed. My kids were so happy 😊😊 to see something different. If you’re looking for something really peaceful, nice, looking at the beautiful nature in the mountains, you are definitely at the right place. Thank you Charlotte for making our stay so special.😊😊😊😊 It was a really good experience and we definitely have to go back….

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