Charlottesville Holiday Rentals

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Holiday Rentals in Charlottesville

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (83)
"This is a great place to stay. Close to town but out on a large very private farm. Highly recommend. "
1802 cottage once part of Monticello and owned by Thomas Jefferson

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

9.8 out of 10, Exceptional, (47)
"This was a perfect spot for exploring Charlottesville for a few days. Loved being so close to the downtown mall, an easy walk to explore shops and restaurants there, and also the great restaurants in the Belmont neighborhood. "
The price is NZ$444
includes taxes & fees
12 Aug - 13 Aug
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (57)
"The cottage was super adorable and perfect for our little weekend getaway!!! "
The price is NZ$568
includes taxes & fees
18 Aug - 19 Aug
Ivy Rose Cottage nestled b/t Cville & Vineyards

Downtown Carriage House | 1 BR Loft close to the historic downtown mall

9.4 out of 10, Exceptional, (69)
"Second stay here and all good!! "
Downtown Carriage House | 1 BR Loft close to the historic downtown mall

Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!

9.8 out of 10, Exceptional, (83)
"The property was great! It was clean, had a great location. Will be back!"
The price is NZ$492
includes taxes & fees
7 Sept - 8 Sept
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!

Cowboy hide-a-way cottage with hot tub on historic farm close to everything

9.4 out of 10, Exceptional, (25)
"Beautiful property the cabin is so cute perfectly situated the hot tub is awesome very clean just a beautiful getaway and not a far drive highly highly recommend"
Cowboy hide-a-way cottage with hot tub on historic farm close to everything

Postcard Cabins Shenandoah

2.0 star property
10.0 out of 10, Exceptional, (22)
"We really enjoyed our stay. Real close to Shenandoah National Park. "
The price is NZ$312
includes taxes & fees
11 Aug - 12 Aug
Postcard Cabins Shenandoah

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (190)
"Quite and Accommodating.office staff was great "
The price is NZ$200
includes taxes & fees
12 Aug - 13 Aug
Valley Extended Suites

Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

10.0 out of 10, Exceptional, (14)
"We loved staying at this property. Easily accommodated our family and was such a pretty setting. Host was excellent in answering questions and providing information. Would definitely stay here in the future."
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

Massanutten's Woodstone Meadows by Tripforth

4.0 star property
9.0 out of 10, Wonderful, (217)
"Nice and quiet place to stay over the weekend and food was great "
Massanutten's Woodstone Meadows by Tripforth

Massanutten Resort by Tripforth

3.0 star property
7.8 out of 10, Good, (152)
"The rooms are fully equipped "
Massanutten Resort by Tripforth

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.6 out of 10, Exceptional, (130)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is NZ$419
includes taxes & fees
13 Aug - 14 Aug
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (289)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is NZ$409
includes taxes & fees
14 Aug - 15 Aug
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

The Summit at Massanutten Resort by Tripforth

3.5 star property
9.2 out of 10, Wonderful, (63)
"Beautiful resort, clean & spacious condo. Lots of activities for the family to enjoy. I recommend staying away from the timeshare presentation they offer guest. "
The Summit at Massanutten Resort by Tripforth

Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

10.0 out of 10, Exceptional, (32)
"We had a beautiful stay and very secluded. We would love to come back. "
Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

Wow! What A View!

9.4 out of 10, Exceptional, (15)
"Découverte de la corse pour la 1ère fois. Proche de tous, plage, équitation mer montagne, spécialités, petit port avec restau,rando, village et super point de vue."
Wow! What A View!

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
The price is NZ$439
includes taxes & fees
11 Aug - 12 Aug
Love Ridge Mountain Lodging

Massanuttens Shenandoah Villas by Tripforth

4.0 star property
7.6 out of 10, Good, (141)
"It was nice."
Massanuttens Shenandoah Villas by Tripforth

Pet friendly! Free Rec passes w/ Mass Resort!

9.0 out of 10, Wonderful, (21)
"great location and amenities"
Pet friendly! Free Rec passes w/ Mass Resort!

Numerous On-Site Trails: Earlysville Wooded Cabin

10.0 out of 10, Exceptional, (71)
"We absolutely loved how beautiful this little cabin is. Loved sitting on the front porch drinking my coffee in the mornings and listening to the birds chirp. This place is so peaceful and relaxing. Barbara was a wonderful host and came over to check to see if we needed anything. Great location to visit all the local towns around the area and only 30 minutes from the Byrd visitor center and Shenandoah national Park. We would definitely stay here again."
Numerous On-Site Trails: Earlysville Wooded Cabin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Charlottesville Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Charlottesville?

Yes, there are holiday rentals in Charlottesville close to Carter Mountain Orchard, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Charlottesville like the majestic mountain landscape and entertainment choices this destination is known for. While you're here, don't miss the university campus and array of shops.

What are some of the best holiday rentals that Charlottesville has to offer?

Massanutten's Woodstone Meadows by Tripforth: This holiday home rental outside of Charlottesville is located near skiing, and has an outdoor pool, an arcade/games room and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Another good choice for your trip to Charlottesville is Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!.

How many holiday rentals will I find in Charlottesville?

With 169 Expedia holiday rentals, you're guaranteed to find just the right place for your Charlottesville stay.

What’s there to see and do in Charlottesville?

Family-friendly attractions include Charlottesville Ice Park and Virginia Discovery Museum, whereas Carter Mountain Orchard and Ix Art Park are a couple of great spots to enjoy the outdoors. While here, Ting Pavilion and Historic Court Square are other places worth a visit.

What’s a holiday rental in Charlottesville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charlottesville. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family getaway.