Guesthouse holiday rentals in Charlottesville

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Top-rated Guesthouses in Charlottesville

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Guest favourite

Guesthouse in Orange

5.0 out of 5 average rating, 183 reviews

Taj Garage Guesthouse

Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.

27 Feb – 6 Mar

$1,418 AUD total

Guest favourite

Guesthouse in Charlottesville

4.97 out of 5 average rating, 118 reviews

Delightful loft cottage in the heart of CVille

A short walk to the Downtown Mall, Main Street shops and restaurants, and the UVA hospital, this brand-new guest house will welcome you to the heart of Charlottesville. Cozy and modern, our light filled sanctuary features high end finishes and warm details. A comfortable desk and high-speed internet makes the space perfectly suited for traveling professionals. Make this your urban home base, as you explore the Virginia outdoors, with dozens of wineries and gorgeous hikes within a short drive.

15 – 22 Aug

$2,235 AUD total

Guest favourite

Guesthouse in Charlottesville

4.98 out of 5 average rating, 246 reviews

Renew @ Coniferidge.

Constructed in 2017 “ Renew” offers a peaceful, clean and simple space furnished with a comfortable modern mix style. It is situated a short distance from the main home and offers just the privacy you are looking for. This property, located outside beautiful Charlottesville Va. is an easy drive to restaurants, shopping, art, culture, wineries, history, parks and the Uva . Flat Screen Smart TV (use your logins to access your favorite sites ) NO pets - out of consideration of future guests

28 June – 5 July

$1,677 AUD total

Guest favourite

Guesthouse in Charlottesville

4.91 out of 5 average rating, 523 reviews

Downtown studio, walk to corner/downtown mall/UVA

Professionally cleaned, intimate space, walking distance to all of C-ville then you have found the right place! Come stay with us and enjoy everything this amazing city has to offer. The house is a separate structure from the main home. It has all the amenities of a hotel room to include off street parking (at no extra cost might I add) . It is centrally located with a 5-12 min walk to the Amtrak, west main shops, Preston Ave, downtown mall, The Corner, and UVA. See "Space" for more details.

2 – 9 July

$1,889 AUD total

Guest favourite

Guesthouse in Crozet

4.98 out of 5 average rating, 118 reviews

Crozet Cottage | Close to Wineries & DT Crozet

Enjoy a cozy getaway at our centrally-located carriage house, in the heart of sought-after Crozet, VA. Completely renovated in 2022, the carriage house feels brand new! Our space offers 1 queen bed and 1 full-bed pull-out couch. The space is .5 miles from downtown Crozet, 2.5 miles to King Family Vineyard and 3.5 miles to Chiles Orchard. It is equipped with a kitchen, a large closet (fits a pack n' play!), high speed internet and Apple TV. We have assigned parking spots in the driveway.

12 – 19 June

$1,503 AUD total

Guest favourite

Guesthouse in Earlysville

4.98 out of 5 average rating, 316 reviews

Cottage at Frog Jump- woodland privacy at its best

Guesthouse ideal for two people. Small cottage (1 bed, 1 bath) is situated in a country setting on ten wooded acres along a large serene pond. It features a darling kitchenette with sink, fridge, microwave and toaster/convection oven. (No stove top, no oven.) You'll enjoy birdsong and views of various wildlife. A quiet, restful place to stay when you want to be near Shenandoah Nat’l Park, UVA, Charlottesville, Virginia wineries, Monticello, Montpelier, CHO, and other close-by attractions.

16 – 23 July

$1,171 AUD total

Guest favourite

Guesthouse in Troy

4.99 out of 5 average rating, 118 reviews

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Take a walk on miles of trails that are adjacent to the property. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

19 – 26 Nov

$1,720 AUD total

Guest favourite

Guesthouse in Charlottesville

5.0 out of 5 average rating, 129 reviews

Luxury tiny house in central Charlottesville

Adjacent to UVA and central to wineries and historic attractions, La Casita is a new tiny home combining modern luxury with central location. La Casita is design-built and offers custom furnishings and luxurious touches in a light-filled space. We are in the residential pedestrian-friendly neighborhood of Fry's Spring, near I 64. Walk to restaurants and Scott Stadium. Enjoy all amenities including a comfortable daytime workspace with high-speed internet.

19 – 26 July

$2,058 AUD total

Guest favourite

Guesthouse in Charlottesville

4.89 out of 5 average rating, 181 reviews

Cozy Modern Private Guesthouse

Private guesthouse/studio in scenic Charlottesville/Crozet. Ideally located near UVA, exceptional wineries, breweries and excellent food scenes all as close as 10 to 15 minutes from your doorstep. The studio offers a very basic kitchenette (see list of items), 1 bedroom w/King bed, an area with a Queen bed, a living room and a dinning room area . Heat/air adjustable per area for your comfort. WiFi for connectivity and Smart TV for your convenience.

3 – 10 Sept

$1,320 AUD total

Guest favourite

Guesthouse in Elkton

4.99 out of 5 average rating, 162 reviews

Noná’s Nest

Noná’s Nest is a quaint one bedroom, one bathroom carriage house, tucked into the peaceful Shenandoah Valley. Centrally located 9.5 miles to the Swift Run Gap entrance of Shenandoah National Park, 12 miles to Massanutten Resort, and 22 miles to Harrisonburg. Enjoy the tranquil country setting and beautiful Blue Ridge Mountain views from the second story deck. Owners live adjacent to carriage house.

15 – 22 Oct

$1,095 AUD total

Guest favourite

Guesthouse in Afton

5.0 out of 5 average rating, 114 reviews

WEEKENDS, WINE & WAHOOS! - Private Detached Studio

Enjoy an escape in the heart of Virginia wine country! This renovated, detached studio is only 22 mins. south of Charlottesville & UVa. Whether you're attending a wedding or exploring everything the area has to offer, it's an ideal spot. You're close to multiple vineyards, Shenandoah NP/The Blue Ridge Parkway, breweries & hiking. Plus, there's fast, reliable internet & your own deck for relaxing.

27 June – 2 July

$1,046 AUD total

Guest favourite

Guesthouse in Troy

4.96 out of 5 average rating, 177 reviews

Cabin in The Pines

The natural wood cabin is conveniently located 12 miles east of Charlottesville on a private 100 acre farm. The owners are on property which is located near Interstate 64, a major shopping center, Martha Jefferson Hospital, University of Virginia as well as many vineyards, breweries, and historic attractions.

18 – 25 July

$1,105 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Charlottesville guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Superhost

Guesthouse in Crozet

4.86 out of 5 average rating, 281 reviews

Stylish Carriage House Suite near Crozet center

6 – 13 June

$2,156 AUD total

Guest favourite

Guesthouse in Charlottesville

5.0 out of 5 average rating, 110 reviews

Hidden Gem near town and Monticello with a pool

24 Nov – 1 Dec

$2,328 AUD total

Guest favourite

Guesthouse in Crozet

4.92 out of 5 average rating, 184 reviews

Crozet Carriage House

25 Sept – 2 Oct

$1,903 AUD total

Guest favourite

Guesthouse in Schuyler

4.9 out of 5 average rating, 356 reviews

Homestead at HeartRock

20 – 27 Feb

$1,469 AUD total

Guest favourite

Guesthouse in Ruckersville

4.98 out of 5 average rating, 255 reviews

Mountain Guesthouse*Hot Tub*WiFi*Firepit*Grill*SNP

9 – 16 Oct

$2,293 AUD total

Guest favourite

Guesthouse in Boston

4.98 out of 5 average rating, 148 reviews

The Bunkhouse- simple & serene w/mountain views

13 – 20 Oct

$1,570 AUD total

Guest favourite

Guesthouse in Charlottesville

4.92 out of 5 average rating, 135 reviews

The Cottage at Eastwood Farm and Winery

1 – 8 Aug

$3,973 AUD total

Guest favourite

Guesthouse in Madison

4.97 out of 5 average rating, 229 reviews

Hebron Valley Cottage

8 – 15 Sept

$1,838 AUD total

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Guesthouses with a patio

Guest favourite

Guesthouse in Reva

4.97 out of 5 average rating, 146 reviews

Adorable cottage with partial blue ridge views

30 Aug – 6 Sept

$1,251 AUD total

Guest favourite

Guesthouse in Mount Crawford

4.95 out of 5 average rating, 108 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

15 – 22 Sept

$1,219 AUD total

Guest favourite

Guesthouse in Barboursville

4.95 out of 5 average rating, 21 reviews

Burnley Cottage

6 – 13 June

$1,517 AUD total

Guest favourite

Guesthouse in Keswick

4.92 out of 5 average rating, 51 reviews

Elegant Keswick guest house with luxurious pool

24 June – 1 July

$2,741 AUD total

Guest favourite

Guesthouse in Charlottesville

5.0 out of 5 average rating, 30 reviews

Home Tract Cottage UVA/Charlottesville/Ivy

13 – 20 Sept

$3,266 AUD total

Guest favourite

Guesthouse in Waynesboro

4.89 out of 5 average rating, 54 reviews

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

24 Sept – 1 Oct

$1,418 AUD total

Superhost

Guesthouse in Keswick

4.85 out of 5 average rating, 26 reviews

The Woodhouse Cottage

3 – 10 May

$1,840 AUD total

Guest favourite

Guesthouse in Charlottesville

4.98 out of 5 average rating, 49 reviews

NEW Tucked Away in Central C-ville.

25 July – 1 Aug

$3,089 AUD total

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Guest house rentals with a washing machine and dryer

Guest favourite

Guesthouse in Gordonsville

4.91 out of 5 average rating, 171 reviews

La Petite Maison at Hedgeapple Hollow

2 – 9 July

$1,715 AUD total

Guest favourite

Guesthouse in Afton

5.0 out of 5 average rating, 223 reviews

Mountain Cottage / Pool, heart of 151 Brew Trail

7 – 14 June

$3,457 AUD total

Guest favourite

Guesthouse in Midland

4.97 out of 5 average rating, 151 reviews

Modern Farm Stay

14 – 21 Oct

$1,556 AUD total

Guest favourite

Guesthouse in Afton

4.92 out of 5 average rating, 514 reviews

Tiny House Bliss. Brew Ridge. Trail. Ski. Wineries

26 Oct – 2 Nov

$2,963 AUD total

Superhost

Guesthouse in Shenandoah

4.87 out of 5 average rating, 256 reviews

Guest House with Game Room & Massage Chair

10 – 17 July

$4,104 AUD total

Guest favourite

Guesthouse in Faber

5.0 out of 5 average rating, 41 reviews

Relaxing Cottage with Firepit

25 Dec – 1 Jan

$1,166 AUD total

Guest favourite

Guesthouse in Charlottesville

4.98 out of 5 average rating, 43 reviews

Charming one room cottage with parking.

30 Dec – 6 Jan

$2,043 AUD total

Guest favourite

Guesthouse in Nellysford

5.0 out of 5 average rating, 38 reviews

The Nest...lovely 2 bedroom apartment in the woods

4 – 11 Mar

$1,593 AUD total

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Quick stats about guesthouse rentals in Charlottesville

Total rentals
30 properties
Local attractions
Shenandoah National Park Trust, University of Virginia and John Paul Jones Arena
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
3.6K reviews

Guesthouse holiday rentals in Charlottesville

Top-rated Guesthouses in Charlottesville

Holiday rentals for every style

Cottages

Cabins

Apartments

Popular amenities for Charlottesville guesthouses

Family-Friendly guesthouses

Guesthouse in Crozet

Guesthouse in Charlottesville

Guesthouse in Crozet

Guesthouse in Schuyler

Guesthouse in Ruckersville

Guesthouse in Boston

Guesthouse in Charlottesville

Guesthouse in Madison

Guesthouses with a patio

Guesthouse in Reva

Guesthouse in Mount Crawford

Guesthouse in Barboursville

Guesthouse in Keswick

Guesthouse in Charlottesville

Guesthouse in Waynesboro

Guesthouse in Keswick

Guesthouse in Charlottesville

Guest house rentals with a washing machine and dryer

Guesthouse in Gordonsville

Guesthouse in Afton

Guesthouse in Midland

Guesthouse in Afton

Guesthouse in Shenandoah

Guesthouse in Faber

Guesthouse in Charlottesville

Guesthouse in Nellysford

Quick stats about guesthouse rentals in Charlottesville

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Rentals with dedicated workspaces

Total number of reviews

Destinations to explore