Guesthouse vacation rentals in Charlottesville

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Popular amenities for Charlottesville guesthouse rentals

Family-friendly guest house rentals

Guest favorite
A charming brick cottage features a sloped metal roof and white-trimmed front door, framed by vibrant greenery and flowering bushes. A grassy area leads to the entrance, creating a welcoming exterior. Soft clouds drift above, adding to the serene outdoor setting.
Guesthouse in Charlottesville
4.91 out of 5 average rating, 147 reviews

The Cottage at Eastwood Farm and Winery

MichaelRating, 5 stars4 months ago
We appreciated being close to family for our Thanksgiving holiday. The proximity to the winery was an added bonus. Would definitely stay again!
Superhost
A bright living area features a cozy sofa adorned with decorative pillows. A vibrant piece of wall art adds color, while a rustic sliding barn door leads to another room. A wooden bar with metal stools offers a casual dining space.
Guesthouse in Crozet
4.86 out of 5 average rating, 308 reviews

Stylish Carriage House Suite near Crozet center

JaniceRating, 5 stars1 month ago
I booked a last minute spontaneous mental health getaway to the mountains of Virginia. I loved the apartment and the hosts were so accommodating. I had everything I needed and more during my stay. My favorite part was the claw leg tub and the deck. Both perfect for winding down. The location is great because there is a lot to do nearby. You can be in Charlottesville or the Shenandoah National Park south entrance in about 20 mins. My only regret is that I didn’t stay longer to enjoy the Airbnb and more of the area.
Superhost
Guesthouse in Charlottesville
4.91 out of 5 average rating, 583 reviews

Downtown studio, walk to corner/downtown mall/UVA

LisaRating, 5 stars1 month ago
From the outside, the property may not look like much, but the inside was a lovely, pristine place to stay. Great location-- I walked to the Downtown Mall a couple of times and a short drive to anywhere else. I loved it and would definitely go back!
Guest favorite
A pebbled pathway is flanked by lush greenery and planters, leading the eye towards a large tree. A small metal table and chairs invite outdoor seating, nestled among the tranquil surroundings of the cottage.
Guesthouse in North Downtown
4.75 out of 5 average rating, 118 reviews

Historic Cottage in Downtown Charlottesville

ColleenRating, 5 stars2 weeks ago
A cute cottage that was perfect for our getaway. It’s tucked away in a cute neighborhood that’s walkable to downtown. Raul was responsive and helpful!
Top guest favorite
A modern studio space features large windows that allow natural light to fill the room. A cozy yellow chair sits beside a small coffee table, with a guitar resting on a stand nearby. The bed area is visible in the background, framed by a stylish shelf.
Guesthouse in Boston
4.98 out of 5 average rating, 189 reviews

The Bunkhouse- simple & serene w/mountain views

MaggieRating, 5 stars2 weeks ago
Came here for our anniversary and it was a great stay! Jenn & Daniel were very kind and responsive. We loved the local food and goods they stocked the kitchen with. It exceeded our expectations, 10/10 would stay again if we did another Shenandoah trip.
A charming two-story house is situated among trees, featuring a red metal roof and light yellow siding. Front steps lead to a welcoming entrance adorned with wreaths. Leafy landscaping surrounds the home, contributing to the serene rural atmosphere.
Guesthouse in Madison
4.82 out of 5 average rating, 87 reviews

Madison Farmette Guest House

LeishaRating, 5 stars1 week ago
We loved staying at this farmhouse! It was peaceful and relaxing. The house was as described and pictured. Jennifer was very friendly and responsive when I accidentally locked myself out of the house. She also left us a lovely treat upon arrival. The bed was comfortable and we slept well. We would stay here again.
Guest favorite
A landscaped front yard features a stone pathway leading to a white cottage. Green shrubs and newly planted flowers frame the path, providing a natural feel. A small porch can be seen in the corner, furnished with two chairs, perfect for outdoor relaxation.
Guesthouse in Charlottesville
4.91 out of 5 average rating, 435 reviews

Hardpan Cottage

ElleRating, 5 stars1 month ago
This stay was so peaceful. I was just passing through Charlottesville for one night and this was the perfect spot to get some rest. I enjoyed a relaxing bath and slept well in the comfortable bed. Erin greeted me upon arrival and was very kind. I’d certainly recommend this stay for solo female travelers or a couple.
Top guest favorite
A serene landscape showcases expansive green fields, framed by rolling hills and colorful autumn foliage. Majestic mountains rise in the distance under a clear blue sky, creating a peaceful and inviting natural setting.
Guesthouse in Charlottesville
5 out of 5 average rating, 123 reviews

Hidden Gem near town and Monticello with a pool

GarrettRating, 5 stars2 months ago
Hidden Gem definitely deserves its name! Beautiful views with things to do in the area. My girlfriend and I enjoyed our weekend getaway!!

Guest house rentals with a patio

Top guest favorite
Lush green grass stretches across the foreground, leading to a scenic vista dominated by rolling hills and misty mountains. The trees display varying shades of green, indicating the freshness of spring, with a backdrop of soft clouds partially covering the peaks.
Guesthouse in Massies Mill
4.99 out of 5 average rating, 78 reviews

Solar-powered Guesthouse at Peak Time Property

GarthRating, 5 stars1 day ago
My girlfriend and I really enjoyed a weekend away here. The property is quite beautiful and secluded, yet is only a short drive away from some of the hiking and breweries that we checked out. It's on our list of places to come back to for a quick weekend getaway!
Top guest favorite
A welcoming living area features a large area rug with floral patterns. Two couches provide comfortable seating, and a flat-screen TV is mounted on the wall. The open layout allows views into the kitchen and dining space, enhancing the connection between areas.
Guesthouse in Mount Crawford
4.96 out of 5 average rating, 154 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

KathyRating, 5 stars1 week ago
We only stayed for 1 night but would definitely have enjoyed more. Pretty much everything you needed was provided. The cabin was clean and cozy ! The bathroom was spacious and well stocked. Bed was comfy and big enough for our daughter to sleep with us. Surrounding area was simple and pretty farmland. We loved meeting Shea !
Guest favorite
The exterior of a light blue house is showcased, featuring a spacious deck with seating and a grill. A landscaped garden with small plants borders the yard, while green hills and trees are visible in the background under a partly cloudy sky.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 54 reviews

Stony Point Cottage

RyleeRating, 5 stars1 day ago
My girls and I had a wonderful time at Gretchen's place. The space was clean and open. The furniture was also extremely comfortable!
Top guest favorite
A charming white house is framed by a vibrant tree with red foliage, set against a clear blue sky. A gravel path leads toward the home, which features a black roof and a welcoming front porch, surrounded by well-maintained grass and shrubs.
Guesthouse in Gordonsville
5 out of 5 average rating, 26 reviews

Guest House at Annandale

IsabelRating, 5 stars2 weeks ago
This cottage was everything we hoped for from the cottage itself, the grounds and the beautiful horses. Best part was being able to pet and feed the horses. Thank you Louis for a memorable stay.
Guest favorite
An open kitchen features a spacious wooden island with black bar stools. Modern appliances are visible, along with open shelving displaying kitchenware. Light grey walls provide a neutral backdrop, while a doorway leads to adjacent areas, enhancing the layout's flow.
Guesthouse in Barboursville
4.98 out of 5 average rating, 52 reviews

Burnley Cottage

CoryRating, 5 stars1 month ago
I can’t say enough positive things about the cottage, the property, and the booking experience start to finish. My husband and I were visiting the area for a couple days for a wedding, and we were just happy to find something so close to the venue that allowed dogs and wouldn’t break the bank. It turned out to be all that and more! Josh and Megan let us know when the cottage was ready and their directions were perfect. The property is secluded, but it’s not too far from civilization if you need groceries/supplies. We watched birds from rocking chairs on the front porch, the WiFi held up beautifully, the TV/Roku had everything we wanted, and the kitchen was fully equipped (and gorgeous!). The surrounding area was ideal for walking our 16-year old pup. We also slept like babies. If we had more time, we’d definitely have enjoyed the local attractions (restaurants, wineries, breweries, parks, museums, etc.). So much to do! We’d happily return!
Top guest favorite
A welcoming kitchen space is displayed with vibrant yellow walls. Stainless steel appliances include a refrigerator and an oven with a hood. A wooden dining table is set with placemats, and natural light filters through the window above the sink.
Guesthouse in Staunton
4.98 out of 5 average rating, 48 reviews

Peaceful rural retreat with pool and spa

PrasadRating, 5 stars2 weeks ago
Karen was an excellent host! Very responsive to my questions about the trip. Guesthouse was very clean and nicely stocked. Felt very peaceful and safe the whole time we were on the property. She gave great suggestions for local restaurants and things to do. Highly recommend staying at the guesthouse and enjoy the warm hospitality!!!
Superhost
Guesthouse in Keswick
5 out of 5 average rating, 5 reviews

3 Cottages on luxurious Keswick estate with pool

TheresaRating, 5 stars1 week ago
Beautiful and peaceful location for gathering with family for a long weekend. The cottages were very nice. We will be back!
Guest favorite
The main living area features high beamed ceilings and large windows that bring in natural light. A mid-century modern sofa and a glass coffee table are positioned for relaxation. A small dining table is visible, and a kitchenette area holds a coffee maker and a wine rack.
Guesthouse in Rapidan
4.98 out of 5 average rating, 48 reviews

Romantic & Private Guest Cottage on a Lovely Farm

DavidRating, 5 stars1 week ago
This place was great. Exactly as pictured and very peaceful. Would definitely stay again and recommend.

Guest house rentals with a washer and dryer

Top guest favorite
The exterior of La Casita features a modern design with smooth gray siding and large windows. A manicured green lawn surrounds the home, with blooming trees providing shade. A small patio area with chairs is visible, inviting outdoor relaxation.
Guesthouse in Charlottesville
5 out of 5 average rating, 167 reviews

Luxury tiny house 3 min from UVA

KaitRating, 5 stars1 week ago
Very responsive. Loved the mini porch and access to the backyard for when the weather is pretty.
Superhost
A modern kitchen features dark cabinetry complemented by light-colored countertops and backsplash. Stainless steel appliances, including a refrigerator and oven, are present. Ample natural light enters through the window, while seating is arranged with white chairs against the wall. A sleek, dark floor enhances the space.
Guesthouse in Belmont
4.7 out of 5 average rating, 149 reviews

Belmont Carriage House

JamesRating, 5 stars6 months ago
Kate’s cottage is in a quaint neighborhood near downtown. Her place is well appointed and very tidy. She is a great host and very friendly and clearly takes pride in making sure her guests are taken care of. Highly recommend this spot and great host!
Top guest favorite
A bright and airy living space features a modern kitchenette with white cabinetry and a dining area with a round table. Cozy seating is presented in red and gray tones, while large windows allow natural light to fill the room. A neutral area rug enhances the inviting atmosphere.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 52 reviews

Charming one room cottage with parking.

ZachRating, 5 stars1 week ago
Catherine's place was lovely and quiet. Perfect place to stay if you want to check out Charlottesville. We could walk to some spots, everything else was just a short Uber ride. Everything was clean and well stocked. Would recommend!
Guest favorite
A corridor links the bathroom and living area, featuring a glass shower and a dual sink vanity with dark cabinetry. A stylish futon is positioned in the living space, with natural light coming from a nearby window. The floor is adorned with wooden planks.
Guesthouse in Harrisonburg
4.93 out of 5 average rating, 83 reviews

Swanky and Modern Downtown Guesthouse

KarenRating, 5 stars1 week ago
Loved the place...well lit with all we needed! Very walkable in a lovely community. Walked to a live show on Friday evening and great farmers market on Saturday morning. Very relaxing and clean space! Would definitely stay again!
Guest favorite
Guesthouse in Afton
4.92 out of 5 average rating, 572 reviews

Elegant Tiny Home Close to Wine, Beer & Mountains

CorinneRating, 5 stars5 days ago
Such a perfect cozy stay! Close to Nelson 151 craft beverage trail and the Rockfish Gap entrance to Shenandoah/Skyline Dr. There was so much to do we honestly wished we stayed longer. We will be back!
Guest favorite
The exterior of the guest house features a clean, modern design with large windows that allow natural light to fill the interior. A well-maintained grassy area surrounds the structure, complemented by lush greenery and a small covered entryway.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 145 reviews

Delightful loft cottage in the heart of CVille

DivyaRating, 5 stars1 week ago
Freeman's little guest house was a perfect place for my academic work trip. The space is so well appointed I could focus to edit my lecture and other writing, dress to feel confident for various meetings with new colleagues across the university (with mirrors in all the right places), and hang out with friendly colleagues for a drink "at my place." Truly a versatile and beautiful space that feels like a home without distractions / a great boutique hotel / and a place to host friends all bundled into one architectural gem with beautiful details.
Guest favorite
A serene pond scene is illuminated by a water fountain, creating reflections on its surface. Surrounding trees provide a natural frame, while soft lighting enhances the peaceful atmosphere. A blue paddle boat is visible along the shoreline, contributing to the tranquil setting.
Guesthouse in Shenandoah
4.96 out of 5 average rating, 73 reviews

Guesthouse with Massage Chair & GAME ROOM

AngelaRating, 5 stars4 days ago
This location is perfect for Ruby Falls and downtown Chattanooga. Just a short drive to both. The place is super clean and comfortable lots of nice touches. Nice neighborhood loved staying here will definitely come back!
Guest favorite
A hot tub is positioned on a wooden deck, providing an unobstructed view of rolling hills and trees. The sky displays soft pastel colors during sunset, enhancing the serene atmosphere of the surrounding countryside.
Guesthouse in Culpeper
5 out of 5 average rating, 21 reviews

Rare Mountain Views in Culpeper ~ Hot tub ~ Arcade

AmberRating, 5 stars1 week ago
Andy & Ling's place is an oasis overlooking the rolling hills of Virgina, equipped with everything you could possibly need to feel right at home. My 16 year old daughter said it was the nicest air BNBs we've ever stayed at.....and that says a lot coming from a teenage girl. Netflix was even included so we didn't have to spend so much time connecting our account. Top notch responses too! Will definitely come again. Thank you for hosting us.

Quick stats about guesthouse rentals in Charlottesville

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    3.6K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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