Charlottesville Holiday Rentals

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Holiday Rentals in Charlottesville

Our top choices for Charlottesville holiday rentals

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (60)
"Loved staying here!"
The price is NZ$601
includes taxes & fees
30 Sept - 1 Oct
Ivy Rose Cottage nestled b/t Cville & Vineyards

Mechum Hill Cottage: Central to Crozet & Cville

9.6 out of 10, Exceptional, (16)
"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 NZ$478
includes taxes & fees
28 Sept - 29 Sept
Mechum Hill Cottage: Central to Crozet & Cville

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

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (39)
"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."
The price is NZ$536
includes taxes & fees
29 Sept - 30 Sept
Unique Cypress cottage, close to Charlottesville with mountain views.

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (89)
"Great place"
1802 cottage once part of Monticello and owned by Thomas Jefferson

Near University of Virginia + CHO

8.0 out of 10, Very good, (1)
"Hardly any sleep the first night! Parties above us and to the side of us too loud! Otherwise the place was relatively clean"
The price is NZ$294
includes taxes & fees
7 Oct - 8 Oct
Near University of Virginia + CHO

Postcard Cabins Shenandoah

2.0 star property
9.6 out of 10, Exceptional, (36)
"Great cabin!! "
The price is NZ$317
includes taxes & fees
28 Sept - 29 Sept
Postcard Cabins Shenandoah

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

3.0 star property
7.8 out of 10, Good, (157)
"Spacious facility, quiet/peaceful atmosphere "
Massanutten Resort by Tripforth

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

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!

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!

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

10.0 out of 10, Exceptional, (243)
"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!

Be Our Guest at Massanutten Resort

10.0 out of 10, Exceptional, (155)
"We had a great trip! The house was a perfect size for our family. "
Be Our Guest at Massanutten Resort

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

9.8 out of 10, Exceptional, (64)
"Everything was perfect and clean and exactly as expected. My family loved staying here. We would definitely recommend it and will book it again if we return to the area."
The price is NZ$714
includes taxes & fees
2 Oct - 3 Oct
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (60)
"Loved our stay - the house, location, and amenities were perfect for us!"
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Massanutten Cabin - Hot Tub, Pool Table, Large Yard, billiards room

9.6 out of 10, Exceptional, (121)
"Really nice house, perfect for our group and proximity to the bike park. "
Massanutten Cabin - Hot Tub, Pool Table, Large Yard, billiards room

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 NZ$317
includes taxes & fees
29 Sept - 30 Sept
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

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$487
includes taxes & fees
25 Sept - 26 Sept
Love Ridge Mountain Lodging

Massanuttens Shenandoah Villas by Tripforth

4.0 star property
7.6 out of 10, Good, (143)
"It was nice."
Massanuttens Shenandoah Villas by Tripforth
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

Find out more about Charlottesville

Find out more about Charlottesville

Everything you need to know about Charlottesville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Charlottesville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Charlottesville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Charlottesville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Charlottesville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Charlottesville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Charlottesville holiday rentals we have selected for you start as low as NZ$294 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Charlottesville rentals

At Expedia, we put the best Charlottesville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Charlottesville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Charlottesville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Charlottesville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 154 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.