Charlottesville Holiday Rentals

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Holiday Rentals in Charlottesville

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 AU$529
includes taxes & fees
10 Aug - 11 Aug
Ivy Rose Cottage nestled b/t Cville & Vineyards

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 AU$413
includes taxes & fees
10 Aug - 11 Aug
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

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

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (81)
"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

Rugby Road Residential -RRR- near UVa and downtown

10.0 out of 10, Exceptional, (32)
"We had a great stay. The owners are kind and responsive, and the property was just as depicted in the photos. We would absolutely stay here again."
The price is AU$390
includes taxes & fees
6 Aug - 7 Aug
Rugby Road Residential -RRR- near UVa and downtown

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

9.8 out of 10, Exceptional, (83)
"Close to Monticello. Great condo. Loved giant window view of the mountains. 3rd floor unit. Very quiet and clean. "
The price is AU$485
includes taxes & fees
2 Sept - 3 Sept
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!

Postcard Cabins Shenandoah

2.0 star property
10.0 out of 10, Exceptional, (20)
"We really enjoyed our stay. Real close to Shenandoah National Park. "
The price is AU$305
includes taxes & fees
5 Aug - 6 Aug
Postcard Cabins Shenandoah

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

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (190)
"Quite and Accommodating.office staff was great "
The price is AU$171
includes taxes & fees
6 Aug - 7 Aug
Valley Extended Suites

Massanutten Resort by Tripforth

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

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

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

9.0 out of 10, Wonderful, (288)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is AU$381
includes taxes & fees
5 Aug - 6 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 AU$404
includes taxes & fees
5 Aug - 6 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!

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (238)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed

10.0 out of 10, Exceptional, (62)
"Enjoyed our stay at this lovely getaway - clean, pleasant and roomy home. "
The price is AU$668
includes taxes & fees
17 Aug - 18 Aug
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
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 acclaimed theatre scene 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 Resort by Tripforth: This holiday home rental outside of Charlottesville is located near skiing, and has an outdoor pool, an arcade/games room and free WiFi to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. 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 172 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.