Charlottesville Holiday Rentals

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Check prices for these dates

Tonight
10 Sept - 11 Sept
Tomorrow
11 Sept - 12 Sept
This weekend
12 Sept - 14 Sept
Next weekend
19 Sept - 21 Sept

Holiday Rentals in Charlottesville

Our top choices for Charlottesville holiday rentals

Ivy Rose Cottage nestled b/t Cville & Vineyards
Fridge, microwave, oven, stovetop

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (59)
"Loved staying here!"
The price is HK$1,395
HK$2,636 total
includes taxes & fees
11 Sept - 12 Sept
Ivy Rose Cottage nestled b/t Cville & Vineyards
Downtown Carriage House | 1 BR Loft close to the historic downtown mall
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (76)
"Great Quite getaway near down town"
Downtown Carriage House | 1 BR Loft close to the historic downtown mall
Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (39)
"Perfect location for winery, golf, dining and shopping in the Crozet and Charlottesville area. I would definitely recommend and consider staying here again."
The price is HK$1,246
HK$2,341 total
includes taxes & fees
11 Sept - 12 Sept
Unique Cypress cottage, close to Charlottesville with mountain views.
1802 cottage once part of Monticello and owned by Thomas Jefferson
Outdoor pool, a heated pool

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (88)
"Historic property just minutes from Monticello (sightseeing) and the Clifton Inn (dinner). While a bit small, it is a very cozy and appealing place. And very quiet. Having your own hot tub and hammock, and practically your own salt pool, is very special."
1802 cottage once part of Monticello and owned by Thomas Jefferson
Mechum Hill Cottage: Central to Crozet & Cville
Outdoor dining

Mechum Hill Cottage: Central to Crozet & Cville

9.6 out of 10, Exceptional, (15)
"Very quiet and peaceful. Large, secluded property. Good base from which to explore area wineries, local beer, food, and hike im the Shenandoah National Park."
The price is HK$1,005
HK$2,172 total
includes taxes & fees
11 Sept - 12 Sept
Mechum Hill Cottage: Central to Crozet & Cville
Loveshack, a charming tiny house on a 5 acre farm
Smart TV

Loveshack, a charming tiny house on a 5 acre farm

9.6 out of 10, Exceptional, (7)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
Loveshack, a charming tiny house on a 5 acre farm
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Property grounds

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10.0 out of 10, Exceptional, (246)
"Thanks for a wonderful stay at your beautiful farm! Great location for visiting wineries and Charlottesville."
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Postcard Cabins Shenandoah
Exterior

Postcard Cabins Shenandoah

2.0 star property
9.8 out of 10, Exceptional, (31)
"We really enjoyed our stay. Real close to Shenandoah National Park. "
The price is HK$722
HK$1,126 total
includes taxes & fees
15 Sept - 16 Sept
Postcard Cabins Shenandoah
Massanutten's Woodstone Meadows by Tripforth
Exterior

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 "
Massanutten's Woodstone Meadows by Tripforth
Massanutten Resort by Tripforth
Indoor pool, outdoor pool

Massanutten Resort by Tripforth

3.0 star property
7.8 out of 10, Good, (155)
"Nice"
Massanutten Resort by Tripforth
Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area
Property grounds

Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area
The Summit at Massanutten Resort by Tripforth
Aerial view

The Summit at Massanutten Resort by Tripforth

3.5 star property
9.0 out of 10, Wonderful, (64)
"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
Wow! What A View!
Exterior

Wow! What A View!

9.4 out of 10, Exceptional, (16)
"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!
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Property grounds

Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

9.8 out of 10, Exceptional, (39)
"Great place...beautiful property and it was cozy and clean."
The price is HK$1,122
HK$1,447 total
includes taxes & fees
22 Sept - 23 Sept
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Massanuttens Shenandoah Villas by Tripforth
Indoor pool, outdoor pool

Massanuttens Shenandoah Villas by Tripforth

4.0 star property
7.6 out of 10, Good, (143)
"It was nice."
Massanuttens Shenandoah Villas by Tripforth
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Miscellaneous

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10.0 out of 10, Exceptional, (240)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Love Ridge Mountain Lodging
Terrace/patio

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 HK$1,504
HK$2,157 total
includes taxes & fees
16 Sept - 17 Sept
Love Ridge Mountain Lodging
Beautiful Big Resort Home,Views, Pool table, Ping Pong, Air Hockey, Foosball
Exterior

Beautiful Big Resort Home,Views, Pool table, Ping Pong, Air Hockey, Foosball

10.0 out of 10, Exceptional, (389)
"Paula was great to work with. The home was just what our family needed to celebrate our daughter’s graduation from JMU. "
Beautiful Big Resort Home,Views, Pool table, Ping Pong, Air Hockey, Foosball
Be Our Guest at Massanutten Resort
Outdoor dining

Be Our Guest at Massanutten Resort

10.0 out of 10, Exceptional, (153)
"This was a lovely well equipped rental in a lovely setting.. "
Be Our Guest at Massanutten Resort
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
Outdoor dining

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

10.0 out of 10, Exceptional, (63)
"We were staying in the area for our son’s graduation and needed a comfortable place for our family to be. The house was perfect for our needs. We’ll definitely be coming back when we can stay longer."
The price is HK$1,051
HK$3,196 total
includes taxes & fees
15 Sept - 16 Sept
🏔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

Oakhurst Inn at the University

Oakhurst Inn at the University

10/10 Excellent
"My wife and I stayed here for the weekend and it was pleasant bliss. The hosts were so kind and staff were very friendly. The cafe food is outstanding. Can’t go wrong here! "
Dan 1-night trip
Posted 17 hours ago
Oakhurst Inn at the University

Find out more about 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 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 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 158 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.