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Guesthouse holiday rentals in Shenandoah Valley

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Shenandoah Valley guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Purcellville
4.81 out of 5 average rating, 275 reviews

Barn Apartment in VA Wine Country

CodyRating, 5 stars1 month ago
An extremely welcoming place that had many things to do and accommodating our autistic children very well! It was a shame we didn't get the chance to make s'mores! We would love to come back to this place sometime since it is so peaceful and homey! We watched older movies that we forgot about! Thanks for the DVDs!
Guest favourite
Guesthouse in Frederick
4.97 out of 5 average rating, 339 reviews

The Shady Bear Cabin

CassidyRating, 5 stars5 days ago
This is a beautiful, private place with amazing nature. We saw deer and hummingbirds, and they were pretty close to us. This place has a wonderful cat (Mr. Moo) who will give you much love! It is a bummer that we didn’t see dogs, but we got to see the chickens and got eggs from them! Amazing place! Although we may not hear beautiful sounds like others mentioned, we felt the peace and mindless presence. We enjoyed our time, and it was a perfect place for our short retreat.
Top Guest favourite
Guesthouse in Farmville
4.98 out of 5 average rating, 296 reviews

BrightEyes Alpaca Retreat Farmville ,Virginia

DanaRating, 5 stars1 week ago
Over the years I've stayed at quite a few Air BnB places, including internationally, and I can fairly say that Cindy and Bill's Air BnB is my favorite so far! Cindy and Bill are amazing hosts and people and their Air BnB reflects that. The attention to detail shows they not only know what creature comforts travelers need (good quality shampoo, conditioner, body wash, and spare toiletries you may have forgotten), but also which little luxuries make an Air BnB feel truly like home (French coffee press, Brita water pitcher, and farm fresh eggs in the kitchen). And if that isn't enough, there's the alpacas and the guardian dogs, Journey and Jilly. Cindy and Bill put a lot of love and time into their animals and it shows. They love to introduce you to them, so definitely take advantage of that! If you want a peaceful surrounding that's within an easy drive to two colleges and the town of Farmville, this is the place. When we are back this way, we're definitely staying here again!!
Guest favourite
Guesthouse in Morgantown
4.95 out of 5 average rating, 487 reviews

Trillium Acres Guest House

ClaireRating, 5 stars2 weeks ago
we had an action packed week and Rebecca's place was a serene, comfortable place to come back to each evening. When all three teenagers tell you the beds were "the best" you know you've got a hit. Trillium Acres is well supplied with quality furnishings and special little touches that made us feel wanted and welcomed. I would recommend Rebecca's Trillium Acres to anyone traveling to this area of WV.
Guest favourite
Guesthouse in Glen Allen
4.84 out of 5 average rating, 561 reviews

Private and Quiet Pool House Convenient Location

BrittanyRating, 5 stars3 days ago
Very lovely. Will visit again!
Top Guest favourite
Guesthouse in Smithsburg
4.97 out of 5 average rating, 743 reviews

Jewel Vinsota Artist's Guesthouse

CassidyRating, 5 stars2 weeks ago
Our second stay here, and we'll definitely be coming back for more. The place has everything you could wish for-- art supplies, musical instruments, a well-stocked kitchen, grilling supplies, and an incredible sculpture garden. The hosts were so responsive and thoughtful. We felt welcomed and cared for throughout the entire experience.
Top Guest favourite
Guesthouse in Gettysburg
4.99 out of 5 average rating, 432 reviews

The Cock and Feather Guesthouse

OscarRating, 5 stars2 days ago
Loved the place. Terrific ambiance. William was a great host and very friendly and helpful. All the extra candy was a very nice touch as well.
Guest favourite
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.

Guesthouses with a patio

Top Guest favourite
Guesthouse in Church Road
5 out of 5 average rating, 210 reviews

Heron Rock: Lakefront Cottage on Lake Chesdin

DorieRating, 5 stars1 day ago
I am so grateful to have found the Heron Rock Cottage. We needed a peaceful place to escape to and the cottage was perfect. The photos don’t do justice for how beautiful the cottage and views are. Anne is also a wonderful host. She is quick to respond and was so sweet to leave a home made dessert for us. We stayed during the week and the lake was so relaxing and beautiful. We enjoyed the dock the entire time we were there, as well as fishing, stand up paddle boards, kayaks, and countless wildlife, including deer and otters. We also liked that they created a nature trail on the property. We picked up groceries on the way there, but everything we needed was stocked in the cottage. I also loved the extra special details for our dog, including towels after she had a fun day in the lake and a blanket for her as well. I definitely recommend anyone who is looking for a relaxing, but fun getaway. We look forward to booking again in the future.
Top Guest favourite
Guesthouse in Mount Crawford
4.96 out of 5 average rating, 157 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

DestinyRating, 5 stars5 days 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
Guesthouse in Troy
4.99 out of 5 average rating, 180 reviews

Beaver Pond Farm - Near Charlottesville

TatumRating, 5 stars5 days ago
My boyfriend and I had a wonderful weekend at Scott and Christi's place. It's very peaceful and we appreciated how friendly and helpful they are. There are ducks, horses, and chickens on the property which you can appreciate from the screened-in porch while sipping your coffee. The drive to Charlottesville is relatively short and very scenic; the house is also close to many popular wineries. We also got some snacks upon our arrival! I appreciate the little ways Scott and Christi went the extra mile to make our stay an enjoyable one!
Guest favourite
Guesthouse in Grantsville
4.95 out of 5 average rating, 164 reviews

“The Loft” Guest House w/wifi workspace, gym etc

JohnRating, 5 stars6 days ago
We enjoyed our stay at the loft. Linda was very helpful and responsive when we had a few minor issues/questions during our first day check in. You could tell Linda put a lot of thought into ensuring guests had all the amenities needed for a comfortable stay. We had everything we needed for a comfortable stay. The A/C thermostat and some of the light/fan switches were located downstairs which was a minor annoyance if you need to make frequent adjustments. This was not a big concern for us, just something to note for those who have limited mobility going up and down stairs. Overall we had a great stay and would recommend it to others.
Top Guest favourite
Guesthouse in Orange
5 out of 5 average rating, 256 reviews

Taj Garage Guesthouse

AnnaRating, 5 stars3 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.
Guest favourite
Guesthouse in Bluemont
4.96 out of 5 average rating, 151 reviews

Blueridge Mountain Guest Cabin- Amongst the Trees

ChristineRating, 5 stars2 weeks ago
Our little getaway was great! Cute little guesthouse with cozy feel. Everything was easy to navigate and use.
Guest favourite
Guesthouse in New Castle
4.95 out of 5 average rating, 148 reviews

Waterfront Cottage Retreat with Hot Tub

AllisonRating, 5 stars1 month ago
We had a lovely time staying in the cottage by the creek! The beds were very comfortable and the kitchen well-stocked with quality appliances. We enjoyed the hot tub and fishing in the creek, there was also plenty of firewood for the fire pit. Cell service in the area was spotty but WiFi in the house worked well. Would definitely stay here again!
Top Guest favourite
Guesthouse in Woodstock
4.96 out of 5 average rating, 139 reviews

Cozy cottage nestled on 8 acres with mountain view

ZachRating, 5 stars2 weeks ago
Nice, cozy guest house in quiet location. Paula was so friendly and was kind enough to introduce us to her horses. Highly recommended.

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in Charlottesville
5 out of 5 average rating, 169 reviews

Luxury tiny house 3 min from UVA

RileyRating, 5 stars3 weeks ago
La Casita was perfect for our needs. It’s great for a couple of small family and packs a lot into a small space. The house is well-maintained and is in a great location for events at UVA, as well as easy access to downtown Charlottesville. Laura was friendly and responsive, and provided clear instructions and useful information. We would definitely stay here again.
Guest favourite
Guesthouse in Bedford
4.87 out of 5 average rating, 282 reviews

The Cottage at Oakwood.Pet Friendly. Self Check in

DanaRating, 5 stars3 weeks ago
We had a wonderful weekend especially for my first time in VA! We were in town for the Storming of Thunder Ridge Memorial Bike Ride. Hunter went above and beyond hosting us and giving us great information about the area, where my daughter could do a warm up ride and super accommodating with her dog. The back patio was beautiful and peaceful! The neighborhood was safe and very close to town and the ride. I just wish that we could have stayed longer! We will definitely be back!
Top Guest favourite
Guesthouse in Broadway
4.98 out of 5 average rating, 102 reviews

Katie's Shenandoah Kottage

GinaRating, 5 stars2 months ago
Katie was great and so was her husband. Both very friendly and very helpful. Their little cottage is very cozy comfortable and convenient. We highly recommend it and hope to go again.
Top Guest favourite
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!
Guest favourite
Guesthouse in Lexington
4.94 out of 5 average rating, 119 reviews

Guest House in the Valley

BenRating, 5 stars5 days ago
Excellent stay. Very friendly hosts. Private setting with stunning mountain views. 10/10 would come back if visiting the area again!
Top Guest favourite
Guesthouse in Purcellville
4.98 out of 5 average rating, 240 reviews

The Cottage at Dunthorpe Farm

RogeRating, 5 stars2 weeks ago
Kelly & Phil were incredible hosts who went above and beyond to give us a comfortable memorable stay! Whether offering restaurant recommendations, stocking the fridge with dairy free drinks and snacks, or bringing a beautiful breakfast of pastries and homemade jam each morning, they showed their thoughtfulness and generosity in all they did. Their property is secluded and gorgeous and has the lovely perk of their two sweet dogs. We’re so grateful they shared their home with us, and we would absolutely stay again any time we’re in the area. We can’t recommend the Cottage enough!
Guest favourite
Guesthouse in Lovettsville
4.96 out of 5 average rating, 226 reviews

Cottage Escape in Virginia Wine Country

ColeRating, 5 stars1 week ago
Best Airbnb service I’ve had in a long time! What a gem of a cottage. Located in such a serene area. The hosts were attentive and flexible and responded so fast. We enjoyed the stay and would definitely go back!
Guest favourite
Guesthouse in Gordonsville
4.91 out of 5 average rating, 182 reviews

La Petite Maison at Hedgeapple Hollow

DedeRating, 5 stars6 months ago
A beautiful peaceful setting with lots of wildlife around. Christina was always very responsive whenever I asked a question or needed something. a great place to stay near to family to celebrate Thanksgiving.

Destinations to explore