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House holiday rentals in Roseland

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Popular amenities for house rentals in Roseland

House rentals with a pool

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

Hot Tub! Wintergreen Resort!

MalenaRating, 5 stars6 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 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!
Guest favourite
Home in Roseland
4.96 out of 5 average rating, 45 reviews

Family-Friendly Meets Luxury

AnabellaRating, 5 stars1 day ago
We choose this home for our 2025 family get together, we were 8 adults, 7 kids and a dog and we were more than comfortable! The house is beautiful! very spacious and very well organized and equipped with everything we needed! Something that stood out to me, comparing this stay with previous ones, there were large size shampoo, body wash and conditioner in every bathroom, as well as large hand soap and refills in every sink and plenty of dishwasher, laundry detergent, TP and paper towel!! That was very very appreciated! The outdoor deck area was just amazing! We created beautiful memories making s’mores and enjoying the hot tab! The kids loved the slide and play area! We truly loved our stay! The only thing that was not to our liking was the pool rules of 6 guests at the time, because we had to split up the family when this vacation was about spending time together, as we all live apart from each other, but this has nothing to do with the rental 🤷🏼‍♀️ We will comeback! 🧡
Superhost
Home in Wintergreen Resort
5 out of 5 average rating, 4 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
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….
Guest favourite
Home in Afton
5 out of 5 average rating, 11 reviews

Saddleback Sanctuary: Luxury Estate beside Veritas

RebeccaRating, 5 stars1 month ago
Beautiful views and a perfect location. The hosts were prompt to respond and I’d love to come back!
Guest favourite
Home in Wintergreen Resort
4.82 out of 5 average rating, 160 reviews

Misty Mountain Cabin w/spa

BenRating, 5 stars1 month ago
The cabin was great to stay at and had some pretty awesome views! Highly recommend the hiking trails. Overall, a really great place.

Weekly house rentals

Top guest favourite
Home in Monroe
4.98 out of 5 average rating, 268 reviews

The Old Parsonage in The Blue Ridge

SamanthaRating, 5 stars1 month ago
A small group of friends and I stayed at Anne’s place for our best friends wedding. Needless to say, this was the perfect spot. Anne’s place was utterly beautiful and peaceful. The house was so cozy and quaint, the family photos on the wall that depicted the home from a different generation made our stay that much more special. We felt so at home and it was the perfect place to unwind and celebrate our friend. Anne went above and beyond by providing us with fresh eggs, juices, and a variety of other breakfast items. Cooking in the rustic kitchen was hands down our favorite part! 10/10 would recommend staying at Anne’s place!
Top guest favourite
Home in Roseland
4.98 out of 5 average rating, 57 reviews

Cozy Farmhouse W/Mountain Views

ErinRating, 5 stars1 month ago
Breanna's farm house was perfect for our family of 4 adults and 4 kids! The space was clean, the beds were awesome and the kids had an amazing time playing in the yard and near the creek. We will be back!
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 stars1 week 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.
Top guest favourite
Home in Roseland
4.98 out of 5 average rating, 89 reviews

Book for Summer! 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

Superhost
Home in Amherst
4.82 out of 5 average rating, 65 reviews

Historic Home in Amherst

LizRating, 5 stars2 weeks ago
Lovely little spot in Amherst. Clean, close to the towns shops and restaurants. Stayed here for SBC reunion and it was convenient to campus.
Guest favourite
Home in Crozet
5 out of 5 average rating, 17 reviews

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

RaymondRating, 5 starstoday
My stay in Crozet was absolutely exceptional thanks to this beautiful property. The home features stunning minimalistic interior design that matched the listing photos perfectly, while the spectacular views and adjacent lavender farm create a truly unique and peaceful atmosphere. The property seamlessly integrates with its natural surroundings, offering a tranquil retreat that feels both luxurious and authentically connected to the Virginia countryside. I highly recommend this home to anyone seeking a rejuvenating getaway—it delivers an outstanding experience that will leave you thoroughly refreshed.
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!
Top guest favourite
Home in Afton
5 out of 5 average rating, 33 reviews

The Vū, Afton w/ 360º Mountain Views

KristaRating, 5 stars1 month ago
We could not have asked for a better stay at the Vū. The home was as beautiful as the photos and the scenic background made it hard to leave. The house is near several vineyards and popular local spots but is set back from the road and neighbors, so felt very private. It’s clear that Emily put careful thought into every detail of the space, from the furniture to the amenities and fully-stocked kitchen. The screened porch was an exceptional feature. I stayed with my family and the space was more than enough to accommodate all of us. I absolutely recommend the Vū for your next mountain getaway!
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 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 Afton
4.97 out of 5 average rating, 36 reviews

Mountain Homestead - Hottub, King, Dogs, Gameroom

AlexRating, 5 stars2 weeks ago
The photos don’t do it justice - the views were immaculate, the location was excellent, and the home was a piece of serenity in Afton. Wendy was a wonderful host, very responsive, and kind. Would rent this again in a heartbeat.

Destinations to explore

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