Charlottesville Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Charlottesville

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

Ivy Rose Cottage nestled b/t Cville & Vineyards

Charlottesville
10.0 out of 10, Exceptional, (62)
"We had a great time, property was very clean when we came in. "
United States
Taylor & Mason S.
The price is ￥27,608
￥52,170 total
includes taxes & fees
Nov 16 - Nov 17
Ivy Rose Cottage nestled b/t Cville & Vineyards
Smart TV
Loveshack, a charming tiny house on a 5 acre farm

Loveshack, a charming tiny house on a 5 acre farm

Charlottesville
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
Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.

Charlottesville
10.0 out of 10, Exceptional, (43)
"The house was fantastic! Great size, location…everything was perfect. Will definitely stay there again!!!"
United States
Mark F.
The price is ￥22,647
￥43,670 total
includes taxes & fees
Nov 16 - Nov 17
Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

2.0 star property
Stanardsville
9.6 out of 10, Exceptional, (48)
"Highly recommend if you like camping but want more of an RV camping experience. Everything was wonderful! "
United States
Christa
The price is ￥19,885
￥29,517 total
includes taxes & fees
Dec 8 - Dec 9
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Property grounds
The Ultimate Escape. Unpack, Relax, Enjoy

The Ultimate Escape. Unpack, Relax, Enjoy

Shipman
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.
The Ultimate Escape. Unpack, Relax, Enjoy
Apartment, 1 Bedroom | Exterior
Massanutten's Woodstone Meadows by Tripforth

Massanutten's Woodstone Meadows by Tripforth

4.0 star property
McGaheysville
9.0 out of 10, Wonderful, (219)
"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
McGaheysville
7.8 out of 10, Good, (158)
"Spacious facility, quiet/peaceful atmosphere "
United States
Lisa
Massanutten Resort by Tripforth
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

Roseland
9.0 out of 10, Wonderful, (298)
"Very nice location and place to stay. The condo was a little beat up though. "
United States
Lance S.
The price is ￥9,557
￥29,082 total
includes taxes & fees
Nov 19 - Nov 20
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Sauna
Fully Loaded 8BR in Wintergreen! Sleeps 23

Fully Loaded 8BR in Wintergreen! Sleeps 23

2.0 star property
Chestnut Springs
Fully Loaded 8BR in Wintergreen! Sleeps 23
Outdoor dining
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed

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

McGaheysville
9.8 out of 10, Exceptional, (65)
"Nice house and clean on the inside. Beds were comfortable. "
United States
Joni H.
The price is ￥20,798
￥64,234 total
includes taxes & fees
Nov 13 - Nov 14
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
Aerial view
The Summit at Massanutten Resort by Tripforth

The Summit at Massanutten Resort by Tripforth

3.5 star property
McGaheysville
9.0 out of 10, Wonderful, (67)
"Great location and it was quiet and clean. Easy check in"
United States
LeAnn
The Summit at Massanutten Resort by Tripforth
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Chestnut Springs
10.0 out of 10, Exceptional, (3)
"Overall great experience. We did take down one smoke detector in down stairs bedroom due to beeping and I did not know where any batteries were. Other than that, everything was great!"
United States
Anonymous traveler
New Build! Log Cabin with Hot Tub in Wintergreen
Exterior
Wow! What A View!

Wow! What A View!

Wintergreen Resort
10.0 out of 10, Exceptional, (54)
"This was our 4th stay and it was great as usual. "
United States
Amy j.
Wow! What A View!
Exterior
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.

Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.

Elkton
10.0 out of 10, Exceptional, (29)
"This place was perfect -- quiet, private, clean, well-appointed, and close to what we wanted to do in Shenandoah. We really enjoyed it, and send many thanks to the hosts."
United States
Stephen H.
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.
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!

Wintergreen
10.0 out of 10, Exceptional, (249)
"A beautiful peaceful stay. The views are spectacular. You won't be disappointed, everything you need is provided. Can't wait to book again"
United States
Terri L.
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Smart TV, DVD player, books, video library
Lotus View Retreat in Yogaville, Chalet with WiFi and AC

Lotus View Retreat in Yogaville, Chalet with WiFi and AC

Buckingham
10.0 out of 10, Exceptional, (8)
"We loved our quick stay. Check in and check out were very low-key, easy, and flexible. The cabin was immaculate and well appointed with everything we could need. "
United States
Corey B.
The price is ￥24,680
￥41,523 total
includes taxes & fees
Nov 18 - Nov 19
Lotus View Retreat in Yogaville, Chalet with WiFi and AC
Interior detail
Afton Mountain Vineyards

Afton Mountain Vineyards

2.5 star property
Afton
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is ￥48,529
￥54,498 total
includes taxes & fees
Nov 16 - Nov 17
Afton Mountain Vineyards
Property grounds
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Wintergreen Resort
9.8 out of 10, Exceptional, (52)
"Great family getaway. While it rained and conditions were terrible for snowboarding/skiing, we had everything we needed to be comfortable while staying at this condo! "
United States
Jamie M.
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall
Smart TV
Massanutten Chalet

Massanutten Chalet

McGaheysville
10.0 out of 10, Exceptional, (44)
"Beautiful home and in close proximity to Massanutten Ski Resort!! "
United States
Gracey Anna Kattie
The price is ￥20,521
￥54,242 total
includes taxes & fees
Nov 16 - Nov 17
Massanutten Chalet
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

Roseland
9.6 out of 10, Exceptional, (140)
"Beautiful condo with everything you need. We appreciated all the little extras including spices in the kitchen, extra toiletries in case we forgot anything, and pet supplies. We enjoyed the music festival events and the dining options too!"
United States
Kathleen L.
The price is ￥16,947
￥38,409 total
includes taxes & fees
Dec 1 - Dec 2
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlottesville Hotel Reviews

The Doyle Hotel

The Doyle Hotel

10/10 Excellent
"bed was awsome- loved the location"
Jacob 2-night trip
Posted 2 days ago
The Doyle Hotel

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 vacation rentals in Charlottesville?

Yes, there are vacation rentals in Charlottesville near Carter Mountain Orchard, or you can select a secluded option if you're looking for extra privacy while you relax. 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 college campus and array of shops.

What's the top vacation rental in Charlottesville?

Massanutten's Woodstone Meadows by Tripforth: Visitors like this Charlottesville vacation home rental. It is located near skiing and has an outdoor pool, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

How many vacation rentals will I find in Charlottesville?

With 182 Expedia vacation rentals, you're sure 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 vacation rental in Charlottesville like?

Vacation rentals are private properties you can book for a long or short time in Charlottesville. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips or small group gatherings.