Guesthouse vacation rentals in Charlottesville

A spacious living area features a mix of comfortable seating, including a large sofa and two armchairs. A small table holds a vase with flowers. Natural light filters through large windows that open to a deck, with greenery visible outside.

5 out of 5 average rating, 108 reviews

Honey House-modern loft near UVA/Monticello

Modern loft style 800sqft guesthouse. Lots of light and privacy in a quiet neighborhood, just 7-10 minutes to Scott Stadium/UVA/restaurants/downtown mall and Thomas Jefferson’s Monticello. Central to many wineries/breweries. You are in nature but close to everything Charlottesville. With a comfortable Queen size bed, and sleeping cot available if necessary. It is clean, comfortable and spacious. A great place to unwind for a good night’s sleep and sweet dreams. (discount apply to weekly/monthly)

4.92 out of 5 average rating, 580 reviews

The exterior of the tiny house is illuminated by string lights, creating a warm ambiance at night. A grassy area is dotted with colorful adirondack chairs. Natural stones are arranged throughout the yard, enhancing the outdoor setting.

Guesthouse in Afton

Spacious Tiny Home Close to Wine, Beer & Mountains

A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most beautiful tiny house in the world. "Big Tiny", built in 2017, is a luxurious retreat that is huge on both character and amenities. This handcrafted home boasts a full-sized kitchen private bedroom, cozy sleeping loft, 2 large screen TVs, and full bath with tub. With a cathedral ceiling and walls of windows, this Escape Traveler XL is the flagship offering of the premiere tiny home builder.

Superhost

A charming metallic exterior of a separate building is shown, featuring a row of glass doors that offer entrance to the space. Lush green grass surrounds the structure, with small plants along the walkway, highlighting a well-maintained outdoor area.

4.91 out of 5 average rating, 595 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.

4.97 out of 5 average rating, 181 reviews

A sleek coffee maker is situated on a wooden countertop beside a blender. Natural light filters through a nearby window, illuminating the workspace that includes a stainless steel sink and a minimalistic mirror above.

Guesthouse in Crozet

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.

A modern cottage is nestled among tall trees, featuring dark green siding and a welcoming porch. Gravel pathways lead to the entrance, bordered by lush greenery and flower planters. Natural light filters through the nearby foliage, creating a serene outdoor setting.

4.98 out of 5 average rating, 287 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

Guesthouse in Earlysville

A serene pond is surrounded by lush greenery, reflecting the clear blue sky above. Various trees line the banks, creating a tranquil natural setting. The still water offers a peaceful atmosphere, inviting moments of relaxation and contemplation in a secluded outdoor space.

4.98 out of 5 average rating, 359 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.

Guesthouse in Earlysville

A spacious studio interior features high ceilings and large windows that invite natural light. A loft area overlooks the living space, accented by reclaimed wood beams. A kitchenette is visible, along with various seating arrangements, including a wooden sofa and contemporary chairs, complemented by minimalist decor.

4.96 out of 5 average rating, 184 reviews

Modern Cottage near Charlottesville

Bright and open studio space that sits on a 2.5 acre parcel and is about 150 feet away from the main house where we live. It is less than 10 minutes to the airport and under 30 minutes to downtown. The space features a kitchenette, one full bath and an open lofted bedroom space (queen size bed) upstairs. The twin beds are located on the main floor. We can only allow a maximum of 2 cars due to limited space on the property. Use of candles or fire stove is not permitted.

4.98 out of 5 average rating, 248 reviews

The exterior of a light-colored carriage house is shown, featuring a metal roof and large garage doors. A flagpole displays the American flag, and a gravel pathway leads to the entrance. Lush greenery surrounds the property, enhancing the tranquil setting.

Guesthouse in Elkton

Noná's Nest

Noná’s Nest is a quaint one bedroom, one bathroom carriage house (located above our detached garage), 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 and Massanutten Mountain views from the second story deck. Owners live adjacent to carriage house.

A bathroom sink area is displayed, featuring neatly stacked gray towels beside two white pump bottles labeled for hand wash. The soft tones and organized arrangement contribute to a clean and functional space.

4.92 out of 5 average rating, 147 reviews

Cavalier Carriage House Suite | Near UVA

Small yet mighty. This carriage house is the perfect retreat for UVA games, special events, and those exploring Charlottesville. Conveniently located within walking distance to Scott Stadium, and a short distance to UVA, Downtown Charlottesville, and 5th Street Station Shopping Center. Hosts have 2 small, friendly dogs (Mac and Pippie) in the main house which may be seen in the patio entrance area. Guests have access to patio and grill.

A welcoming entrance is shown, featuring a black door with a small window. Stone steps lead up to the door, surrounded by natural landscaping with green foliage and a stone path. The exterior is clad in blue siding, complemented by a white trim.

4.96 out of 5 average rating, 294 reviews

Walk to UVa from our Charming Tiny Home

Walk to UVa from this brand-new 250sq ft "tiny home". Its perfect for game days (1 mile walk along sidewalks to Scott Stadium) or a stylish alternative to hotels for events or work travel! This cottage features a open floor plan with vaulted ceiling, a living room with TV/WiFi, kitchenette, bathroom with tub/shower and sleeping loft. Accommodates 1-4 people looking for a modern, comfortable and centrally-located place to stay.

An open living area is showcased with modern furnishings and a large kitchen space. A round coffee table sits on a textured rug, accompanied by green ottomans and a cozy sofa. Natural light floods in through tall windows and glass doors, enhancing the bright atmosphere.

5 out of 5 average rating, 169 reviews

Luxury tiny house 3 min from UVA

La Casita is a new tiny home combining modern luxury with central location adjacent to UVA, central to wineries, and 10 minutes from Monticello. La Casita is design built to offer custom furnishings and luxurious touches. 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 high-speed internet.

A well-maintained detached studio is set in a landscaped yard featuring artificial grass. A wooden deck with seating overlooks the space. The entrance is accessible via a wide staircase, leading to a serene outdoor area with lounge chairs and a swimming pool.