
Guesthouse vacation rentals in Charlottesville
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Top-rated guesthouse rentals in Charlottesville
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Charlottesville guesthouse rentals
Family-friendly guest house rentals

The Cottage at Eastwood Farm and Winery
We appreciated being close to family for our Thanksgiving holiday. The proximity to the winery was an added bonus. Would definitely stay again!

Stylish Carriage House Suite near Crozet center
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.

Downtown studio, walk to corner/downtown mall/UVA
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!

Historic Cottage in Downtown Charlottesville
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!

The Bunkhouse- simple & serene w/mountain views
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.

Madison Farmette Guest House
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.

Hardpan Cottage
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.

Hidden Gem near town and Monticello with a pool
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

Solar-powered Guesthouse at Peak Time Property
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!

Country Cabin near JMU/ Skyline Dr / Massanutten
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 !

Stony Point Cottage
My girls and I had a wonderful time at Gretchen's place. The space was clean and open. The furniture was also extremely comfortable!

Guest House at Annandale
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.

Burnley Cottage
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!

Peaceful rural retreat with pool and spa
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!!!

3 Cottages on luxurious Keswick estate with pool
Beautiful and peaceful location for gathering with family for a long weekend. The cottages were very nice. We will be back!

Romantic & Private Guest Cottage on a Lovely Farm
This place was great. Exactly as pictured and very peaceful. Would definitely stay again and recommend.
Guest house rentals with a washer and dryer

Luxury tiny house 3 min from UVA
Very responsive. Loved the mini porch and access to the backyard for when the weather is pretty.

Belmont Carriage House
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!

Charming one room cottage with parking.
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!

Swanky and Modern Downtown Guesthouse
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!

Elegant Tiny Home Close to Wine, Beer & Mountains
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!

Delightful loft cottage in the heart of CVille
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.

Guesthouse with Massage Chair & GAME ROOM
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!

Rare Mountain Views in Culpeper ~ Hot tub ~ Arcade
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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- Massanutten Resort
- Luray Caverns
- Ash Lawn-Highland
- Chisholm Vineyards at Adventure Farm
- Lake Anna State Park
- Spring Creek Golf Club
- Prince Michel Winery
- Early Mountain Winery
- Massanutten Ski Resort
- Hermitage Country Club
- Frontier Culture Museum
- The Foundry Golf Club
- Wintergreen Resort
- Car and Carriage Caravan Museum
- NGCOA Mid-Atlantic
- The Plunge Snow Tubing Park