Charlottesville Holiday Rentals

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Check prices for these dates

Tonight
27 Oct - 28 Oct
Tomorrow
28 Oct - 29 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Charlottesville

Fridge, microwave, oven, stovetop
Ivy Rose Cottage nestled b/t Cville & Vineyards
Ivy Rose Cottage nestled b/t Cville & Vineyards
10.0 out of 10, Exceptional, (61)
"Loved staying here!"
United States
Rebecca E.
The price is HK$1,434
HK$2,687 total
includes taxes & fees
30 Oct - 31 Oct
Ivy Rose Cottage nestled b/t Cville & Vineyards
Exterior
Unique Cypress cottage, close to Charlottesville with mountain views.
Unique Cypress cottage, close to Charlottesville with mountain views.
10.0 out of 10, Exceptional, (42)
"The cabin was beautiful and a perfect place for us to relax. The location was phenomenal and closely located to Shenandoah and many amazing towns to explore."
United States
Derek S.
The price is HK$1,204
HK$2,282 total
includes taxes & fees
17 Nov - 18 Nov
Unique Cypress cottage, close to Charlottesville with mountain views.
Smart TV
Loveshack, a charming tiny house on a 5 acre farm
Loveshack, a charming tiny house on a 5 acre farm
9.4 out of 10, Exceptional, (10)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
United States
Zachary G.
Loveshack, a charming tiny house on a 5 acre farm
Exterior
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (46)
"Great cabin!! "
United States
Sami
The price is HK$1,235
HK$1,752 total
includes taxes & fees
28 Oct - 29 Oct
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Property grounds
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
10.0 out of 10, Exceptional, (15)
"Check in was smooth. The cabin was absolutely gorgeous. It was a perfect getaway for our Family. "
United States
Chris h.
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
Exterior
Massanutten's Woodstone Meadows by Tripforth
Massanutten's Woodstone Meadows by Tripforth
4.0 star property
9.0 out of 10, Wonderful, (218)
"Nice and quiet place to stay over the weekend and food was great "
United States
Pablo
Massanutten's Woodstone Meadows by Tripforth
Indoor pool, outdoor pool
Massanutten Resort by Tripforth
Massanutten Resort by Tripforth
3.0 star property
7.8 out of 10, Good, (158)
"Spacious facility, quiet/peaceful atmosphere "
United States
Lisa
Massanutten Resort by Tripforth
Outdoor dining
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
9.8 out of 10, Exceptional, (65)
"Nice house and clean on the inside. Beds were comfortable. "
United States
Joni H.
The price is HK$1,049
HK$3,240 total
includes taxes & fees
28 Oct - 29 Oct
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (297)
"Very nice location and place to stay. The condo was a little beat up though. "
United States
Lance S.
The price is HK$816
HK$1,893 total
includes taxes & fees
9 Nov - 10 Nov
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Exterior
Wow! What A View!
Wow! What A View!
10.0 out of 10, Exceptional, (53)
"Property was gorgeous with amazing mountain views! Comfortable beds, beautiful kitchen and large living room for relaxing. Great location. Can’t wait to stay here again!"
United States
Timmie T.
Wow! What A View!
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen
New Build! Log Cabin with Hot Tub in Wintergreen
10.0 out of 10, Exceptional, (2)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
The price is HK$5,507
HK$9,936 total
includes taxes & fees
30 Oct - 31 Oct
New Build! Log Cabin with Hot Tub in Wintergreen
Miscellaneous
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
10.0 out of 10, Exceptional, (247)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
United States
Martha J.
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Aerial view
The Summit at Massanutten Resort by Tripforth
The Summit at Massanutten Resort by Tripforth
3.5 star property
9.0 out of 10, Wonderful, (66)
"Beautiful resort, clean & spacious condo. Lots of activities for the family to enjoy. I recommend staying away from the timeshare presentation they offer guest. "
United States
Shaunte'
The Summit at Massanutten Resort by Tripforth
Indoor pool, outdoor pool
Massanuttens Shenandoah Villas by Tripforth
Massanuttens Shenandoah Villas by Tripforth
4.0 star property
7.6 out of 10, Good, (144)
"It was nice."
United States
MICHELLE
Massanuttens Shenandoah Villas by Tripforth
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, (331)
"Very comfortable with considerate hosts. Easy walking distance to resort. Highly recommend!"
United States
Kristen H.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Outdoor dining
Be Our Guest at Massanutten Resort
Be Our Guest at Massanutten Resort
10.0 out of 10, Exceptional, (158)
"Great little place!"
United States
Kristin D.
Be Our Guest at Massanutten Resort
Pool
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
9.6 out of 10, Exceptional, (137)
"Very clean place and very accommodating host"
United States
Jeff
The price is HK$855
HK$1,928 total
includes taxes & fees
3 Nov - 4 Nov
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
TV, fireplace, DVD player, books
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing
9.0 out of 10, Wonderful, (152)
"Perfect place to stay if you’re visiting the Shenandoahs."
United States
Jack W.
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing
Smart TV, fireplace, DVD player, books
Great Massanutten Contemporary Property (Sleeps 10) - Military Discount Avail
Great Massanutten Contemporary Property (Sleeps 10) - Military Discount Avail
8.4 out of 10, Very good, (45)
"Great place for family to gather for JMU events."
United States
Elizabeth B.
Great Massanutten Contemporary Property (Sleeps 10) - Military Discount Avail
Exterior
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.
10.0 out of 10, Exceptional, (29)
"Amazing location right up against the national park land. Very nicely furnished and well appointed in every way!"
United States
Chris W.
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.
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

DoubleTree by Hilton Hotel Charlottesville

DoubleTree by Hilton Hotel Charlottesville

10/10 Excellent
"the beds were great, but the pillows were horrible."
James 2-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Charlottesville

Find out more about Charlottesville

Search for holiday rentals in Charlottesville on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlottesville using one of the methods below:

  • View our selection of featured holiday rentals in Charlottesville
  • Use the map to find apartments and other holiday homes in the Charlottesville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Charlottesville while they last

Look no further and take a look at our great range of rental properties in Charlottesville!

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 great live music 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.

How many holiday rentals will I find in Charlottesville?

With 181 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.