
Guest house holiday rentals in Charlottesville
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Top-rated guest house rentals in Charlottesville
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Popular amenities for guest house rentals in Charlottesville
Family-friendly guest house rentals

The Cottage at Eastwood Farm and Winery
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!

Stylish Carriage House Suite near Crozet center
I highly recommend this comfortable place. the host is kind and very responsive. I enjoyed my stay and time in Crozet. LaNae

The Bunkhouse- simple & serene w/mountain views
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!

Hebron Valley Cottage
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!

Hidden Gem near town and Monticello with a pool
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!

Luxury 2BR Suite One Mile From UVa, Near Downtown
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!

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

Homestead at HeartRock
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

Solar-powered Guesthouse at Peak Time Property
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!

Country Cabin near JMU/ Skyline Dr / Massanutten
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.

Guest House at Annandale
What an amazing sanctuary to relax between graduation events. Directions were perfect and the horses, they make the stay truly special.

Burnley Cottage
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.

Belmont Hidden Gem
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!

Taj Garage Guesthouse
The Taj Garage never disappoints! We first stayed here about three years ago and its standards have not dropped since. Highly recommend this darling accommodation.

Historic HomeTract Cottage UVA/Charlottesville/Ivy
We had a lovely time! Thank you

Luxurious Keswick guest house with pool
Wonderful stay at Leah’s cottage. Pool was really great, and the home had everything we needed.
Guest house rentals with a washing machine and dryer

The Loft at St. George
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!

Charming one room cottage with parking.
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!

Delightful loft cottage in the heart of CVille
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!

Guesthouse with Massage Chair & GAME ROOM
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.

Stony Point Cottage
Stony Point Cottage was perfect for our getaway! Lovely location! Hosts were very accommodating! Everything was wonderful!

Rare Mountain Views in Culpeper ~ Hot tub ~ Arcade
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.

Katie's Shenandoah Kottage
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.

Nona's Cottage-Waynesboro/Shenandoah Valley, VA
Have stayed in Nona's Cottage several times -- our favorite Airbnb of all places we travel!
Quick stats about guest house rentals in Charlottesville
Total rentals
30 properties
Nightly prices starting at
$51 SGD 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
- Early Mountain Winery
- Chisholm Vineyards at Adventure Farm
- Lake Anna State Park
- Prince Michel Winery
- The Foundry Golf Club
- Spring Creek Golf Club
- Massanutten Ski Resort
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- The Plunge Snow Tubing Park
- Frontier Culture Museum
- Hermitage Country Club
- Car and Carriage Caravan Museum