Guest house holiday rentals in Charlottesville

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Top-rated guest house rentals in Charlottesville

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Guest favourite

Guest house 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.

30 Aug – 6 Sep

$159 SGD per night

Guest favourite

Guest house 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.

11–18 Jul

$240 SGD per night

Guest favourite

Guest house 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.

5–12 Jul

$196 SGD per night

Guest favourite

Guest house in Charlottesville

4.98 out of 5 average rating, 247 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

29 Jun – 6 Jul

$177 SGD per night

Guest favourite

Guest house in Crozet

4.98 out of 5 average rating, 119 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.

31 Aug – 7 Sep

$176 SGD per night

Guest favourite

Guest house in Earlysville

4.98 out of 5 average rating, 317 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 Dec

$126 SGD per night

Guest favourite

Guest house in Troy

4.99 out of 5 average rating, 119 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.

20–27 Nov

$198 SGD per night

Guest favourite

Guest house 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 Jul

$223 SGD per night

Guest favourite

Guest house 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.

2–9 Sep

$137 SGD per night

Guest favourite

Guest house 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

$127 SGD per night

Guest favourite

Guest house 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.

7–12 Jun

$155 SGD per night

Guest favourite

Guest house 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 Jul

$121 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for guest house rentals in Charlottesville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Superhost

Guest house in Crozet

4.86 out of 5 average rating, 282 reviews

Stylish Carriage House Suite near Crozet center

6–13 Jun

$232 SGD per night

Guest favourite

Guest house in Charlottesville

5.0 out of 5 average rating, 110 reviews

Hidden Gem near town and Monticello with a pool

16–23 Aug

$261 SGD per night

Guest favourite

Guest house in Crozet

4.92 out of 5 average rating, 185 reviews

Crozet Carriage House

15–22 Aug

$201 SGD per night

Guest favourite

Guest house in Schuyler

4.9 out of 5 average rating, 356 reviews

Homestead at HeartRock

22–29 Nov

$164 SGD per night

Guest favourite

Guest house in Ruckersville

4.98 out of 5 average rating, 255 reviews

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

26 Sep – 3 Oct

$254 SGD per night

Guest favourite

Guest house in Boston

4.98 out of 5 average rating, 148 reviews

The Bunkhouse- simple & serene w/mountain views

8–15 Sep

$185 SGD per night

Guest favourite

Guest house in Charlottesville

4.92 out of 5 average rating, 135 reviews

The Cottage at Eastwood Farm and Winery

24 Jun – 1 Jul

$436 SGD per night

Guest favourite

Guest house in Madison

4.97 out of 5 average rating, 229 reviews

Hebron Valley Cottage

27 Oct – 3 Nov

$212 SGD per night

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Guest house rentals with a patio

Guest favourite

Guest house in Reva

4.97 out of 5 average rating, 146 reviews

Adorable cottage with partial blue ridge views

27 Oct – 3 Nov

$137 SGD per night

Guest favourite

Guest house in Mount Crawford

4.95 out of 5 average rating, 109 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

23–30 Dec

$140 SGD per night

Guest favourite

Guest house in Fort Valley

4.9 out of 5 average rating, 144 reviews

Romantic Mountain Getaway⛰ hot tub*king bed*sauna

11–18 Jul

$293 SGD per night

Guest favourite

Guest house in Barboursville

4.95 out of 5 average rating, 21 reviews

Burnley Cottage

6–13 Jun

$172 SGD per night

Guest favourite

Guest house in Charlottesville

4.98 out of 5 average rating, 49 reviews

NEW Tucked Away in Central C-ville.

6–13 Jul

$214 SGD per night

Guest favourite

Guest house in Keswick

4.92 out of 5 average rating, 51 reviews

Elegant Keswick guest house with luxurious pool

21–28 Oct

$317 SGD per night

Guest favourite

Guest house in Waynesboro

4.89 out of 5 average rating, 54 reviews

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

3–10 May

$142 SGD per night

Guest favourite

Guest house in Charlottesville

5.0 out of 5 average rating, 30 reviews

Home Tract Cottage UVA/Charlottesville/Ivy

13–20 Sep

$354 SGD per night

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Guest house rentals with a washing machine and dryer

Guest favourite

Guest house in Gordonsville

4.91 out of 5 average rating, 171 reviews

La Petite Maison at Hedgeapple Hollow

2–9 Aug

$195 SGD per night

Guest favourite

Guest house in Afton

5.0 out of 5 average rating, 223 reviews

Mountain Cottage / Pool, heart of 151 Brew Trail

26 Sep – 3 Oct

$371 SGD per night

Guest favourite

Guest house in Midland

4.97 out of 5 average rating, 151 reviews

Modern Farm Stay

6–13 Oct

$170 SGD per night

Guest favourite

Guest house in Afton

4.92 out of 5 average rating, 514 reviews

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

26 Oct – 2 Nov

$314 SGD per night

Superhost

Guest house in Shenandoah

4.87 out of 5 average rating, 256 reviews

Guest House with Game Room & Massage Chair

7–14 Jul

$466 SGD per night

Guest favourite

Guest house in Lynchburg

4.77 out of 5 average rating, 109 reviews

Charming guesthouse in the heart of Boonsboro

12–17 May

$203 SGD per night

Guest favourite

Guest house in Faber

5.0 out of 5 average rating, 41 reviews

Relaxing Cottage with Firepit

8–15 Apr

$134 SGD per night

Guest favourite

Guest house in Charlottesville

4.98 out of 5 average rating, 44 reviews

Charming one room cottage with parking.

6–13 Oct

$221 SGD per night

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Quick stats about guest house rentals in Charlottesville

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

Guest house holiday rentals in Charlottesville

Top-rated guest house rentals in Charlottesville

Holiday rentals for every style

Cottages

Cabins

Houses

Popular amenities for guest house rentals in Charlottesville

Family-friendly guest house rentals

Guest house in Crozet

Guest house in Charlottesville

Guest house in Crozet

Guest house in Schuyler

Guest house in Ruckersville

Guest house in Boston

Guest house in Charlottesville

Guest house in Madison

Guest house rentals with a patio

Guest house in Reva

Guest house in Mount Crawford

Guest house in Fort Valley

Guest house in Barboursville

Guest house in Charlottesville

Guest house in Keswick

Guest house in Waynesboro

Guest house in Charlottesville

Guest house rentals with a washing machine and dryer

Guest house in Gordonsville

Guest house in Afton

Guest house in Midland

Guest house in Afton

Guest house in Shenandoah

Guest house in Lynchburg

Guest house in Faber

Guest house in Charlottesville

Quick stats about guest house rentals in Charlottesville

Total rentals

Local attractions

Popular amenities

Wifi availability

Rentals with dedicated workspaces

Total number of reviews

Destinations to explore