Guest house holiday rentals in Charlottesville

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Popular amenities for guest house rentals in Charlottesville

Family-friendly guest house rentals

Guest favourite
Guest house 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
Guest house in Crozet
4.86 out of 5 average rating, 313 reviews

Stylish Carriage House Suite near Crozet center

LaNaeRating, 5 stars2 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 favourite
Guest house 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 favourite
Guest house 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 favourite
Guest house 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
Guest house 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 favourite
Guest house 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 favourite
Guest house 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 favourite
Guest house 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 favourite
Guest house in Mount Crawford
4.96 out of 5 average rating, 157 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

DestinyRating, 5 stars1 week 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 favourite
Guest house 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 favourite
Guest house in Barboursville
4.98 out of 5 average rating, 57 reviews

Burnley Cottage

KaraRating, 5 stars2 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 favourite
Guest house in North Downtown
4.95 out of 5 average rating, 41 reviews

Belmont Hidden Gem

JenniferRating, 5 stars1 week 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 favourite
Guest house in Orange
5 out of 5 average rating, 256 reviews

Taj Garage Guesthouse

AnnaRating, 5 stars4 weeks ago
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.
Top guest favourite
Guest house 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
Superhost
Guest house in Keswick
4.93 out of 5 average rating, 42 reviews

Luxurious Keswick guest house with pool

RobertRating, 5 stars1 month ago
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

Top guest favourite
Guest house 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 favourite
Guest house in Charlottesville
4.98 out of 5 average rating, 55 reviews

Charming one room cottage with parking.

AmandaRating, 5 starstoday
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 favourite
Guest house 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 favourite
Guest house in Shenandoah
4.95 out of 5 average rating, 93 reviews

Guesthouse with Massage Chair & GAME ROOM

ClaytonRating, 5 stars2 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 favourite
Guest house 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 favourite
Guest house 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 favourite
Guest house in Broadway
4.98 out of 5 average rating, 103 reviews

Katie's Shenandoah Kottage

TammyRating, 5 stars5 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 favourite
Guest house 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 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

Destinations to explore