Vacation rentals in Keswick

Spaniel Hill; cozy hilltop home w privacy & views

Cozy hilltop with Views, deck and hot tub. Cottage furnished with original art and antiques collected by us, the cottage is easy to get to but feels like a world away. Recently renovated main level has three cozy bedrooms and 1.5 baths, sleeps 6, and the garden level suite offers one large king bed and a twin bed with full bath and separate sink area, sleeps 3. Close to UVA, Pantops 250 corridor, theDowntown Mall, Gordonsville and Orange to our north. Over 20 highly rated wineries within 20 m

One Level Living at Shadwell Terrace

Set in the heart of Wine Enthusiast’s Wine Region of the Year, this newly renovated 2-bedroom, 850 sq/ft terrace level flat with separate entrance, is located in a private setting in the Keswick area. Close to Downtown Charlottesville, we are adjacent to Clifton Inn and Glenmore and minutes to Keswick Hall. After exploring many of Virginia’s wineries, breweries, and historical sites, kick your feet up between the trees in the hammock or share your adventures online with our high speed Wi-Fi.

A private apartment with Self Check-in.

This newly renovated one bedroom apartment is in the heart of the historic district of Gordonsville. No box stores here, just quaint shops and restaurants. The apartment is right on Main Street nestled in the middle of boutique shops and brick sidewalks with Monticello, Montpelier, the University of Virginia, Shenandoah National Park, local vineyards and many historic sites near by. This is a private second story apartment above a local business with a separate entrance and key-less entry.

The Cottage at Hardware Hills Vineyard

Head for the Hills! The Cottage at Hardware Hills Vineyard sits atop the property alongside the main estate house. Bask in Virginia sunsets over the vines. Take a short hike down to the Hardware River where you can dip a toe in or try your hand at fishing. On weekends, you have a family-owned winery right in your front yard to stroll down and sit by the vines to enjoy delicious wines. Centrally located to many wine trail attractions and all that the Charlottesville area has to offer.

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

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. 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 a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

5 local Vineyards Keswick Cottage on Horse Farm

Located in the heart of Keswick Wineries and Horse Country;this eclectic, cozy, unique studio apartment was featured in Country Accents magazine.Enjoy morning coffee on expansive deck overlooking several horses, numerous wildlife, deer, fox, turkey and more! Features bar seating kitchenette, full bath, southwestern painted sinks, loft bedroom overlooking downstairs hearth fireplace, French door entrance into second bedroom. Small Pets only- larger pets by approval

Gordonsville Guest Cottage - private studio

Welcome to the Gordonsville Guest Cottage, located in historic Gordonsville, VA. This is the perfect escape into small-town living, with all the necessities nearby. Close to numerous vineyards and historic sites. Relax and unwind in this 300 sq ft private guest house which includes a queen bed, living area, bathroom, and kitchenette. This cottage is in our backyard and next to train tracks. You will need to walk 150 feet from dedicated parking. No pets.

The Loft at Minor Mill - Private loft apartment.

Our place is a newly constructed barn loft in our 1960's barn. Enjoy beautiful views of the surrounding countryside from large windows and a private balcony. The barn is surrounded by our horse pastures and neighboring fields. Self check in with the key lockbox. This loft is separate from the main house where we live. Private parking and entrance for our guests directly outside of barn loft (this is separate from the main house driveway).

Tranquil Estate Cottage + Art Studio

Guests consistently say the sunsets alone are worth the stay! We've had anniversary trips, proposals, creative retreats, and gal pal gatherings looking for fun. This area boasts award winning vineyards, gardens and history buffs enjoy Monticello and Montpelier. Our peaceful cottage offers the perfect space for couples, creatives, and anyone craving beauty just 10 minutes from downtown C'ville. *Read "Your Property"

The Little House: Screened Porch + Pasture Views

Are you looking for a relaxing getaway weekend in Virginia's countryside? Welcome to The Little House! This tiny house (~300 sq ft) is located on five acres overlooking a private pasture in the scenic countryside of Gordonsville. Located just a 3-minute drive from downtown Gordonsville, the home is the perfect launching point to some of Central Virginia's best wineries, historic sites, and area attractions.

Golden Meadows a Pet-Friendly Country Farm House

Pet-Friendly Country Farm House on Pond Farm stay hosted by Julie and Rick Bring your dogs. We have a huge fenced yard for them to play in. Come and enjoy the peace and quiet. We have 40 acres of fields and woods to help you relax a little. With over a mile of maintained trails you can take your pet for a long walk.  Have a corn hole match or barbecue and just relax. Wineries and breweries are nearby.