Guesthouse holiday rentals in Frederick County

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Popular amenities for Frederick County guesthouses

Family-Friendly guesthouses

Superhost
Guesthouse in Frederick
4.83 out of 5 average rating, 36 reviews

The Wander Inn

KristinaRating, 5 stars1 month ago
I stayed for a little over a month while waiting to close on my house and really enjoyed it. Rani left out fresh fruit and provided breakfast items that came in handy and saved me some money on eating out. I slept comfortably each night and the radiator in the bathroom is better than any space heater. When I was feeling a little down I’d pop out back and watch the horses and a cute pair of cardinals. The view is gorgeous. I also became friendly with sweet gray cat and their bouncy, adorable dogs. All this made it feel like being at home. Rani was kind, welcoming, and warm in every interaction. Some after work chats were such a good reprieve from the stress of the office. 10/10 place.
Top Guest favourite
Guesthouse in Smithsburg
4.97 out of 5 average rating, 748 reviews

Jewel Vinsota Artist's Guesthouse

AnastasiaRating, 5 starstoday
My family had an idyllic time here. Perfect home base for hiking and swimming at the state parks in the area. Good to know for families since it’s hard to tell in photos: - This is essentially a studio apartment, meaning there aren’t full walls that separate the bedroom from the living space so bring a white noise machine - there is wonderful natural light in the apartment but some are sky lights that will be impossible to cover for naptime. That being said, we had a wonderful time with our 4mo old and 4 year old. They have hummingbirds and birds of all colors and lots of instruments, games, and art to experiment with. If your kids are between crawling age to 3 yrs old, all the things in the apartment may stress you out, but it was perfect for a curious 4 year old. We walked the art hike in the backyard at least once a day, which our dog loved, and Sarah even set us up with their firepit to make s’mores. Magical! Truly a trip to remember! We hope to visit again!
Guest favourite
Guesthouse in Frederick
4.98 out of 5 average rating, 184 reviews

Last Min Getaway! Disc offer due to cancellation!

TiffanyRating, 5 stars1 week ago
The lovely “cottage” on Deb‘s property was gorgeous, serene & just what the dr ordered for this exhausted DC mom! Deb couldn’t have been more welcoming; provided an amazing spread of fresh fruits, cookies, a lemon cake, wine, bagels w/cream cheese & OJ in the fridge. Super appreciated as we didn’t arrive until 9:30PM the 1st night. The 1st few days, my teen son & I enjoyed the tranquility of the property, including the refreshing pool & plenty of fun activities nearby. Then, my husband (who had to work), picked up our son so I cld decompress & have a couple much-needed days to hang out w/girlfriends who joined me @ the cottage. Although our last full day was a tad rainy, it didn’t deter us from having a delish brunch in town, checking out the arts festival by the canal & stepping into some cool stores on the main st of vibrant Frederick. Deb‘s accommodations were uber-plush; by far the most luxurious AirBnB I’ve ever stayed in. Thank you so much for the cathartic reset, Deb! 😮‍💨
Guest favourite
Guesthouse in Frederick
4.97 out of 5 average rating, 339 reviews

The Shady Bear Cabin

CassidyRating, 5 stars2 weeks 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.
Guest favourite
Guesthouse in Middletown
4.94 out of 5 average rating, 291 reviews

Indulge, Fresh Flowers, Frederick County Haven

ElciraRating, 5 stars3 weeks ago
Incredible home away from home!!! It's hard to describe all the little things they have to make your stay pleasant and comfortable. They have everything that u can think off and some more, even a nail clipper, board games, laundry room with soap etc etc. We stayed only for a night, but loved every minute there!!!

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Keymar
4.98 out of 5 average rating, 65 reviews

Historic country guesthouse, newly renovated.

RoyRating, 5 stars1 month ago
Enjoyed our stay, wish we had more time. It was very peaceful and relaxing. A good spot to travel to Frederick and Emmitsburg. Loved the ambiance when we checked in with music and snacks waiting for us for our visit!
Guest favourite
Guesthouse in Mount Airy
4.96 out of 5 average rating, 125 reviews

Treasured Hideaway on the Hill

DianeRating, 5 stars3 weeks ago
The bed is probably the most important thing for us when choosing a rental. The master bedroom bed was excellent. The second bedroom, not so much. But if you don’t have back issues, it’s ok. We are really bed snobs 🥺
Superhost
Guesthouse in Frederick
4.83 out of 5 average rating, 36 reviews

The Wander Inn

KristinaRating, 5 stars1 month ago
I stayed for a little over a month while waiting to close on my house and really enjoyed it. Rani left out fresh fruit and provided breakfast items that came in handy and saved me some money on eating out. I slept comfortably each night and the radiator in the bathroom is better than any space heater. When I was feeling a little down I’d pop out back and watch the horses and a cute pair of cardinals. The view is gorgeous. I also became friendly with sweet gray cat and their bouncy, adorable dogs. All this made it feel like being at home. Rani was kind, welcoming, and warm in every interaction. Some after work chats were such a good reprieve from the stress of the office. 10/10 place.
Guest favourite
Guesthouse in Lovettsville
4.96 out of 5 average rating, 229 reviews

Cottage Escape in Virginia Wine Country

MiaRating, 5 starstoday
We loved staying at Dustin’s place! It was the perfect place for a weekend getaway. It was in a great location for beautiful views but also things to do (breweries nearby and a concert in town on Saturday). Dustin was incredibly responsive and wanted to ensure we had a great time. Would definitely recommend this place to others!!
Top Guest favourite
Guesthouse in Smithsburg
4.97 out of 5 average rating, 748 reviews

Jewel Vinsota Artist's Guesthouse

AnastasiaRating, 5 starstoday
My family had an idyllic time here. Perfect home base for hiking and swimming at the state parks in the area. Good to know for families since it’s hard to tell in photos: - This is essentially a studio apartment, meaning there aren’t full walls that separate the bedroom from the living space so bring a white noise machine - there is wonderful natural light in the apartment but some are sky lights that will be impossible to cover for naptime. That being said, we had a wonderful time with our 4mo old and 4 year old. They have hummingbirds and birds of all colors and lots of instruments, games, and art to experiment with. If your kids are between crawling age to 3 yrs old, all the things in the apartment may stress you out, but it was perfect for a curious 4 year old. We walked the art hike in the backyard at least once a day, which our dog loved, and Sarah even set us up with their firepit to make s’mores. Magical! Truly a trip to remember! We hope to visit again!
Guest favourite
Guesthouse in Frederick
4.98 out of 5 average rating, 184 reviews

Last Min Getaway! Disc offer due to cancellation!

TiffanyRating, 5 stars1 week ago
The lovely “cottage” on Deb‘s property was gorgeous, serene & just what the dr ordered for this exhausted DC mom! Deb couldn’t have been more welcoming; provided an amazing spread of fresh fruits, cookies, a lemon cake, wine, bagels w/cream cheese & OJ in the fridge. Super appreciated as we didn’t arrive until 9:30PM the 1st night. The 1st few days, my teen son & I enjoyed the tranquility of the property, including the refreshing pool & plenty of fun activities nearby. Then, my husband (who had to work), picked up our son so I cld decompress & have a couple much-needed days to hang out w/girlfriends who joined me @ the cottage. Although our last full day was a tad rainy, it didn’t deter us from having a delish brunch in town, checking out the arts festival by the canal & stepping into some cool stores on the main st of vibrant Frederick. Deb‘s accommodations were uber-plush; by far the most luxurious AirBnB I’ve ever stayed in. Thank you so much for the cathartic reset, Deb! 😮‍💨
Guesthouse in Fort Ritchie
New place to stay

Lieutenant's Lodge

PetraRating, 5 stars1 month ago
Joyce is an excellent host and fort Ritchie is an amazing place to stay. We’d love to come back!
Guesthouse in Fort Ritchie
New place to stay

Barrick's Bungalow

TamikoRating, 5 stars4 weeks ago
Space was great. Spacious and nicely modernized into a little house, within a historic building and former military base. Beautiful surroundings with a bar and grill and a breakfast and lunch restaurant in easy walking distance. Hoat communicated well and told us we could check in a little early which was great for having a little down time between soccer games.

Destinations to explore