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, 148 reviews

The Cottage at Eastwood Farm and Winery

MelissaRating, 5 stars2 months ago
My daughter‘s wedding was at the tent at Eastwood so we rented the cottage. It was perfect for getting ready! Really cute little place!
Superhost
A well-lit kitchen area features a blend of modern and rustic elements, including a farmhouse-style island with seating. Light streams through the double French doors, leading to a small dining space with two chairs and a circular rug on the floor.
Guesthouse in Crozet
4.86 out of 5 average rating, 313 reviews

Stylish Carriage House Suite near Crozet center

LaNaeRating, 5 stars3 days ago
I highly recommend this comfortable place. the host is kind and very responsive. I enjoyed my stay and time in Crozet. LaNae
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, 194 reviews

The Bunkhouse- simple & serene w/mountain views

EmmaRating, 5 stars3 weeks ago
What a treasure! My mom and I got away for a couple days at Jenn’s place (a wellness sanctuary) and it was so peaceful and lovely, despite the rain we ran into! The place is tranquil both inside and out (a backyard meadow you can frolic in!), and the amenities are wonderful. Fresh bread, eggs, cream (dairy and non-dairy!), butter were all delicious, and I was so obsessed with the local teas and other goodies that I had to go visit the local apothecary that sold them. Jenn and her partner were super responsive to every need, bringing us eye masks and extra cream! Bonus - book a massage with Jenn. Seriously one of the best I’ve ever had. We had a wonderful time, thank you! Hope to be back!
Top guest favorite
A covered porch area is visible, featuring several outdoor chairs and a table. The porch is bordered by a gravel path and landscaped with stones and flowers. The expansive grassy field extends beyond the structure under a clear blue sky.
Guesthouse in Madison
4.97 out of 5 average rating, 250 reviews

Hebron Valley Cottage

JustinRating, 5 stars2 months ago
We spent two nights at David’s place and it was a wonderful place to come back to after a long hike. The cottage was clean and cozy, but the one of the highlights of our trip was watching the sunset on the patio. The property is spectacular! Also bonus points for the mini muffins! Thank you for a great stay!
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, 124 reviews

Hidden Gem near town and Monticello with a pool

LoweryRating, 5 stars3 weeks ago
This is just someone opening their home, it is someone who loves to host; and it shows! Not only was the view incredible but the place felt like a home. From the little details (the “I forgot it at home” box, plenty of pool and bathroom towels, shampoo/conditioner/bodywash, having freshly ground coffee/sugar/sweetener, having spices and any kitchen utensils you could need, and even a heart keychain on the door and my name on the chalkboard). The bed was so comfortable and the shower pressure was amazing. The pool was great (although the weather was a little too cold for us to enjoy it fully)! The ceiling upstairs on one side of the bed was a little low but it was fine and worth it for a king bed. Every uber driver we had didn’t mind waiting for us as he just looked at the view. Would definitely stay here again!
Superhost
A spacious living area features a light-colored sofa and a wooden coffee table. Bright lighting illuminates the room, which opens to a modern kitchen with bar seating. A large mirror with a colorful frame enhances the sense of space, while plush carpet adds comfort.
Guesthouse in Charlottesville
4.82 out of 5 average rating, 45 reviews

Luxury 2BR Suite One Mile From UVa, Near Downtown

Rich Rating, 5 stars2 months ago
This was our second unit we had with Matt at the same time! A truly great stay in Charlottesville with him, we really enjoyed our short stay – the house was a clean and very welcoming for sure! It was truly Awesome location - seemingly 1mile everywhere, and always great comms with Matt always, nice to have in a host for sure. Definitely one of our better picks we have had in that area ! Many thanks again, we will certainly try and stay here again with Matt, if and when the opportunity arises!
Guest favorite
The guesthouse exterior features a rustic wooden façade with a shingled roof. A spacious deck enhances the entryway, adorned with potted plants and grass arrangements. An umbrella stands in a seating area, providing shade for outdoor relaxation, amid a backdrop of trees.
Guesthouse in Ruckersville
4.98 out of 5 average rating, 282 reviews

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

KatherinRating, 5 stars3 weeks ago
The Fox Den is one of the cleanest places we've ever stayed. We enjoyed watching the sunset from the hot tub, roasting marshmallows at the outdoor fireplace, grilling steak, and simply relaxing for a couple of days. The cottage had everything we needed for cooking and grilling. Although the cottage and hot tub are located next to the main house, we still felt a sense of privacy. We've been visiting different Airbnbs annually in the VA and PA areas, and the location of this one was excellent. We followed two of the recommendations from the provided guidebook, and they were amazing (Carter's Mountain Orchard and Fiorano Restaurant).
Guest favorite
A natural stone patio is surrounded by trees, featuring a vintage cast iron tub as a focal point. The space is complemented by two planters filled with colorful flowers and an adjacent wooden table, enhancing the outdoor setting.
Guesthouse in Schuyler
4.91 out of 5 average rating, 390 reviews

Homestead at HeartRock

ZoeRating, 5 stars1 month ago
My boyfriend and I came out here looking for a place to disconnect and Heartrock was the perfect place! Greg gave us a great hiking recommendation to Fortune’s Cove and Kim was so helpful and responsive. The place was so nice and the scenery was lovely. Bilbo the cat was even more friendly than we imagined and we enjoyed hanging with him. We did prep our own breakfast and dinner before arriving just due to the smaller kitchen but it had everything we needed. We took a stroll around the property and it was lovely. The water pressure here is also great. Overall, we had a great time and would definitely come back.

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, 82 reviews

Solar-powered Guesthouse at Peak Time Property

HayleyRating, 5 stars4 weeks ago
I absolutely loved our stay at Leigh’s place. I genuinely cannot recommend this spot enough if you’re needing to get away and just unwind. Beautiful surroundings, quiet, and just overall very peaceful. Leigh was such a great and accommodating host! We will be back!
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, 158 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

DestinyRating, 5 stars2 weeks ago
Cute little house right beside a field of curious cows! Great for us this weekend because we were not really there much. There were a few cameras outside which made it feel like you didn't have total privacy. Close to host's residence, which was fine just not expected. RV parked right outside the front door obstructing some views. But overall worth it and would probably stay again.
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, 29 reviews

Guest House at Annandale

MeredithRating, 5 stars1 month ago
What an amazing sanctuary to relax between graduation events. Directions were perfect and the horses, they make the stay truly special.
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, 57 reviews

Burnley Cottage

KaraRating, 5 stars3 weeks ago
We had a Great weekend get away for my wife’s Birthday. Shenandoah Nation Park was a short drive away with lists of trails. Plenty of Winery and Brewery in the area as well. The place is beautifully built and the kitchen was fully equipped for me to make dinners. There was also a large yard perfect for our Chocolate Lab to run.
Top guest favorite
A cozy living area features a light-colored sofa adorned with decorative pillows and a wooden coffee table. Local art pieces decorate the walls, complemented by a small dining table set for two. Natural light enters through a window, brightening the space.
Guesthouse in Charlottesville
4.95 out of 5 average rating, 41 reviews

Belmont Hidden Gem

JenniferRating, 5 stars2 weeks ago
Great little extended weekend getaway at the Belmont Hidden Gem. Very clean and fresh, nicely appointed and perfect location for our trip. Having a private parking spot adjacent to the Airbnb is super convenient. The accommodations are better than described along with a very comfortable bed. Convenient location to all downtown has to offer and more. Ann thank you again for the coffee beans, fresh cream and recipe idea. Thanks for a wonderful stay!
Top guest favorite
A newly constructed guesthouse features a charming exterior with a sloped red roof and white trim. A covered balcony with a red umbrella overlooks landscaped gardens. Stone pathways and greenery surround the home, enhancing the inviting outdoor space.
Guesthouse in Orange
5 out of 5 average rating, 257 reviews

Taj Garage Guesthouse

ChRating, 5 stars2 weeks ago
Our host was very thoughtful and considerate about our needs. The place was amazing. I would recommend this location . It is also closed to town and shops.
Top guest favorite
A covered front porch features a mix of seating options, including wicker chairs and a small table. Hanging planters add greenery, while potted plants contribute to the inviting setting. The porch overlooks mature landscaping, providing a serene outdoor environment.
Guesthouse in Charlottesville
5 out of 5 average rating, 77 reviews

Historic HomeTract Cottage UVA/Charlottesville/Ivy

AllaireRating, 5 stars3 weeks ago
We had a lovely time! Thank you
Guest favorite
A spacious outdoor pool area features a large heated pool flanked by sun loungers under a clear blue sky. Comfortable seating arrangements with gray cushions and vibrant green accent pillows surround a tray with refreshments, creating an inviting space for relaxation.
Guesthouse in Keswick
4.93 out of 5 average rating, 44 reviews

Luxurious Keswick guest house with pool

GarrettRating, 5 stars1 week ago
Leah’s place worked out great and was close to Keswick Resort so we enjoyed the restaurant and spa there. Pool was a perfect addition and happened to be completely private to us during our stay.

Guest house rentals with a washer and dryer

Top guest favorite
A wooden shelf is mounted to the wall, displaying a set of six clear glass cups, a white mug, and several white plates and bowls. A fire extinguisher is positioned nearby, and a piece of artwork is visible at the bottom of the image.
Guesthouse in Crozet
5 out of 5 average rating, 40 reviews

The Loft at St. George

DanielRating, 5 stars1 week ago
Jen and her place were amazing! She kindly accommodated an early check-in and even left a homemade treat for us. The space was charming, spotless, and perfect for a quick weekend stay. If we’re ever back in Crozet, we’ll definitely stay with Jen again!
Top guest favorite
The entrance displays a white door framed by a small overhang, flanked by two potted evergreen shrubs. A window to the left allows natural light to enter, while soft sunlight illuminates the light gray siding of the cottage.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 55 reviews

Charming one room cottage with parking.

AmandaRating, 5 stars1 day ago
This was the perfect spot for what I needed. It was decorated very cute and it was clean. I liked that it was private, had pots and pans to use, and a little patio set-up too. The host was very responsive and pro active in letting me know check-in and checkout and any other things that I needed. Will definitely stay here again if I’m in the area. Thank you!
Guest favorite
A modern kitchen features marble countertops and contemporary cabinetry. An oven, stovetop, and microwave are visible. A vase with flowers adds a touch of color. A door opens to a private patio with outdoor seating and views of a large tree.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 150 reviews

Delightful loft cottage in the heart of CVille

NateRating, 5 stars3 weeks ago
This Charlottesville loft is the perfect place to get away to the city for a few days! Clean and modern with all the essentials on-hand and close by, we truly loved our stay. Plus, the location is great to get out and enjoy all the wonderful things Charlottesville has to offer! We would return!
Guest favorite
A hot tub is situated under a wooden pavilion, highlighted by soft lighting that enhances the serene atmosphere. The water features a calming blue hue, complemented by surrounding curtains that elegantly frame the space, providing a cozy retreat for relaxation.
Guesthouse in Shenandoah
4.95 out of 5 average rating, 93 reviews

Guesthouse with Massage Chair & GAME ROOM

ClaytonRating, 5 stars3 days ago
Winston and Katherine’s guest house was the perfect launch point for our hike through Shenandoah. Clean, solid, and modern without feeling sterile—this place had everything we needed to gear up and get a good night’s rest before hitting the trail. Tucked away and quiet, but with all the essentials dialed in. Check-in was smooth, and the hosts clearly know what they’re doing. If you’re looking for a solid spot to crash before getting out into the wild, this is it.
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, 62 reviews

Stony Point Cottage

SusanRating, 5 stars1 week ago
Stony Point Cottage was perfect for our getaway! Lovely location! Hosts were very accommodating! Everything was wonderful!
Top 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, 28 reviews

Rare Mountain Views in Culpeper ~ Hot tub ~ Arcade

RosellaRating, 5 stars2 weeks ago
We had a great stay and loved the Mountain View from the hot tub, games and Netflix access was thoughtful. Was clean and had everything we needed, a lot of thoughtful touches. So quiet for peaceful sleep but close to downtown where we could walk and grab good coffee and food.
Top guest favorite
A large maple tree provides shade over a wooden deck, featuring two hanging swing chairs. Green grass and flower pots can be seen surrounding the area, creating a serene outdoor space. A storage shed is visible in the background, hinting at the property's spaciousness.
Guesthouse in Broadway
4.98 out of 5 average rating, 104 reviews

Katie's Shenandoah Kottage

TammyRating, 5 stars6 days ago
Katie's Kottage was a lovely place to stay. It was peaceful and very relaxing. The bed was comfortable. I appreciated that Catherine included so many ideas for activities in the area. The had a basket full of pamphlets. Catherine and Richard were very friendly. We would definitely stay again if we are in the area.
Guest favorite
Guesthouse in Waynesboro
4.92 out of 5 average rating, 73 reviews

Nona's Cottage-Waynesboro/Shenandoah Valley, VA

VermadelRating, 5 stars1 month ago
Have stayed in Nona's Cottage several times -- our favorite Airbnb of all places we travel!

Quick stats about guesthouse rentals in Charlottesville

  • Total rentals

    30 properties

  • Nightly prices starting at

    R723 ZAR 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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