
Holiday houses in Charlottesville
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Top-rated holiday rentals in Charlottesville
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Charlottesville
Top Guest favourite

Home in Charlottesville
5 out of 5 average rating, 23 reviewsCasa Crozet
MattRating, 5 stars1 week ago
Host very responsive given our short notice to book. House is in a great location for a winery weekend. Spacious home with great furnishings and comfy beds. Would stay here again. A extra coffee mug or two to add to the cupboards would be a plus 😜. Overall satisfied with our experience.
Guest favourite

Home in McGaheysville
4.85 out of 5 average rating, 33 reviewsAltitude Adjustment Awaits!
MatthewRating, 5 stars2 weeks ago
Nice place and only about 5 minutes from most of what you want to do at Massanutten.
Guest favourite

Home in McGaheysville
4.96 out of 5 average rating, 51 reviewsIn Resort- Family fun- Kids Suite-Game Room
NikitaRating, 5 stars3 months ago
Our family of 6 had an incredible time at this beautiful AirB&B near Massanutten, VA. The home was absolutely perfect for our getaway. It was spacious, cozy, and had a backyard that we loved—plenty of space for the kids to run around and play! The location was ideal for both skiing at Massanutten and sightseeing; we also had an amazing visit to Luray Caverns, which was just a short drive away. The home truly felt like a home away from home. It had everything we needed, from toiletries to welcome snacks, and even games for family fun. The kitchen was fully stocked, making it easy to cook meals—honestly, we only needed to buy food & seasonings. The host was incredibly responsive, ensuring we had everything we needed and that our stay was seamless. We will definitely be coming back for another stay. It was a perfect vacation for our family, and we couldn't have asked for a better place to stay! Highly recommend.
Superhost

Condo in Wintergreen Resort
4.88 out of 5 average rating, 163 reviewsWander Lodge: Golf, Spa, Wine, or just a getaway
CatherineRating, 5 stars2 months ago
This was the perfect spot for our trip. A friend of mine and I brought our teenage sons for a quick weekend snowboarding trip, and needed somewhere with three sleeping areas. The loft had 2 beds and a fully bath which was exactly what we needed for the boys. It was super convenient to everything with a shuttle stop right out front. Plenty of parking, great amenities, clean, and easy to find! Also very cozy! We’ll definitely return!
Guest favourite

Barn in North Garden
4.89 out of 5 average rating, 190 reviewsPrivate - Mountain View's & Hot tub! PETS OK
HollyRating, 5 stars6 days ago
We had an awesome stay lots of winery’s and ciders to check out ! Loved all of them the view and the hot tub had to be out our favorite and the dog loved running around . The place was so cozy felt so at home and safe! We will so be back thanks for being so awesome !
Top Guest favourite

Apartment in Wintergreen Resort
5 out of 5 average rating, 8 reviews3 Ridges 3 min walk to slopes,besides inn,King bed
KrisRating, 5 stars1 month ago
I've stayed in Wintergreen a few times. This is a lovely condo. Checking in was super easy with a code from the host. Parking was available right in front of the residence. The bed was giant and comfortable. The kitchen and living room was a nice open space with a big smart TV. There is a small backyard with a beautiful view and patio furniture. Everything was clean and the wifi worked well. I would definitely stay here again it was well worth the price.
Top Guest favourite

Home in Nellysford
5 out of 5 average rating, 28 reviewsFoxy Retreat Stoney Creek/ Wintergreen Golf/ Ski
CarlyRating, 5 stars1 week ago
We had a great time at the foxy retreat this past weekend! The house is adorable and has so much space. The backyard feels so private and was such a fun place to hang out. Tammy was a great host, and gave us all the information we needed!
Superhost

Cabin in Gordonsville
4.75 out of 5 average rating, 4 reviewsYURIT / CABIN Rental Available with Amenity
ChinghaoRating, 5 stars57 months ago
Th place is part of a resort so we can use quite a few amenities. Some of the stuff are free (pool and mini golf) while others require a small fee ( rent omg a boat or horseback riding). Overall the place is clean. This is also our first time in a yurit and we really enjoy the experience. Do note that this is an enhanced version or a tent. When it rains. You do hear every drop of it. We did wake up a few times in the middle of the night for that. Overall a great experience though. Definitely will want to come back again.
Quick stats about holiday rentals in Charlottesville
Total rentals
950 properties
Total number of reviews
62K reviews
Family-friendly rentals
520 properties are a good fit for families
Pet-friendly rentals
290 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
510 properties have a dedicated workspace
Destinations to explore
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- Cottage rentals Charlottesville
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- Townhouse rentals Charlottesville
- House rentals Charlottesville
- Rentals with a washing machine and dryer Charlottesville
- Rentals with pools Charlottesville
- Fitness-friendly rentals Charlottesville
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- Guesthouse rentals Charlottesville
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Massanutten Resort
- Luray Caverns
- Ash Lawn-Highland
- Chisholm Vineyards at Adventure Farm
- Lake Anna State Park
- Early Mountain Winery
- Spring Creek Golf Club
- Prince Michel Winery
- The Foundry Golf Club
- Hermitage Country Club
- Frontier Culture Museum
- Massanutten Ski Resort
- Wintergreen Resort
- The Plunge Snow Tubing Park
- NGCOA Mid-Atlantic
- Car and Carriage Caravan Museum