
Guesthouse vacation rentals in Western Maryland
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Top-rated guesthouse rentals in Western Maryland
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Popular amenities for Western Maryland guesthouse rentals
Family-friendly guest house rentals

Barn Apartment in VA Wine Country
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!

Riverkeeper Inn
We enjoyed William’s hospitality. The place was located in a beautiful secluded spot by the Potomac river. So relaxing watching the sun come out behind the mountain and reflecting on the river in the morning, and birds singing. Dogs had a blast too! In case the info is useful, the wifi connection was perfect for working remotely. Lots of beautiful hikes in the area. Thank you

Cottage on our horse farm
I can't wait to go back! The house itself was more than comfortable for 2 very large dogs and my husband and I. The property is very serene, private and just beautiful! Sitting outside you can watch their 3 horses in the pasture or look at the lake (or walk around it) with it's gorgeous white water lilies. If your looking for a place to destress or just looking for a quiet area, this is the place. My dog's go 160 and 114, so you can bring your pups here too

Private detached garage suite
Had a great stay. Would recommend to others.

Historic Herndon In-law house, kitchen. By IAD.
Very beautiful Airbnb !!! Private and very quiet neighborhood , everything we needed was in the unit down to the Keurig pods , extra perk for the rice cooker and Instapot. The bed was spacious and very comfortable It was like being in our own oasis Lots of memorable moments and will always cherish our time there Check out as a breeze and will definitely come back again if we need another get away

CozyLeesburgCottage-Private Home Downtown Leesburg
Beautiful house and great location! Host's instructions were very clear and helpful. It was a perfect spot to stay in when visiting Leesburg! Highly recommend and look forward to staying here again!

The Wander Inn
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.

"Cabbin" at Mountain Home B&B
This place was our best choice even before we realized there would be a freshly-prepared, multi-course gourmet breakfast. House is as advertised, clean, and well-located. Scott and Lisa are friendly, responsive, and fantastic cooks. Enjoy!
Guest house rentals with a patio

Wine Country Loft
We booked Lisa's place for a wedding in the area. Everything looked exactly like the pictures. Despite being above their garage, we found it to be safe & quiet. My husband really enjoyed the projector screen. We really didn't get to utilize the kitchen, but there was plenty there to make meals if you wanted. The fire pit set up was cute & we wish we would have been able to use it, but again.. we were too busy with other wedding activities. Our only complaint was that we found the mattress to be a bit firm, which we enjoy a softer mattress, so this is more of a personal preference & not letting it negatively impact our review. During our stay, we got to meet Lisa & Joseph. Both were extremely nice & gave us great recommendations. We also got to meet their adorable, friendly dog. They were even kind enough to allow our friend to park & hang with me at the loft before we had to be at the wedding. They also gave us a heads up about the town's festival happening & street closures.

Ventura Cottage: 360-views/HotTub/4 acres/Gym
Everything was top notch, pictures don't do the location justice. The ambiance is peaceful quiet fresh air beautiful views, the house is as listed and more, You get what you paid for. Leena is an amazing person very responsive and very hospitable. Don't think twice just book you will not be disappointed.

The Cottage
My girlfriend, our dog, and I stayed for over 30 days at this peaceful spot on Paxon Road in Round Hill, and it was exactly what we were looking for. The property is quiet, secluded, and surrounded by nature Wildlife wandered nearby and was totally unbothered by us or our dog. We loved being so close to a bunch of great wineries and breweries, too. The host was very responsive and made the whole stay easy. Highly recommend for anyone looking for a calm, nature-filled getaway.

A lovely cottage in The Plains, Virginia
My husband and I had a quiet weekend in The Plains and absolutely loved staying at Elizabeth's cottage! The cottage has exquisite furniture, cozy bedding and all the right touches to feel at home. I loved sipping coffee and watching the horses grazing in the pasture. Elizabeth and her family were so friendly and welcoming. We enjoyed walking to town for dinner and shopping. I can't wait to return to explore more of the area.

18th Century Middleburg Cottage
Convenient location to downtown Middleburg and a very comfortable place to stay. We were in town for a wedding at The Goodstone Inn and enjoyed the close proximity to the venue and to town. Tim's went above and beyond with a special welcome amenity as well as providing us with an iron upon request. Tim was very responsive and helpful during our stay and we would not hesitate to stay again when visiting the area. Thank you Tim for a wonderful weekend.

The Woodstock (VA) Hippie House
The Hippie House was super-cute and comfortable. Space was very well-used and nice. The little town of Woodstock was also adorable. Wish we could’ve stayed longer but we’re just passing through.

Private Lake House in western MD
Kurt was very helpful and responsive before we arrived on the property. The views were stunning and the house was gorgeously done. A very pleasant stay

Cozy cottage nestled on 8 acres with mountain view
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 washer and dryer

Skyhorse Retreat Guest House
This was our first time to the area. My best friend was getting married at Bluemont Winery. Everything was as expected at the guest house. We loved our stay. We got to meet Bob and chat some. We did some hiking close by and saw the beautiful overlook. We had a tour all day Saturday of the wineries with a large group from the wedding. Brunch on Sunday at The Local. We even met Zena, one of the dogs, who was very friendly. We would definetly stay again. Thank you Nancy and Bob

The Nest on Nixon Road
This was my second stay at The Nest on Nixon Road, and once again, it was absolutely perfect. Returning felt incredibly comfortable and familiar—everything was just as clean, peaceful, and thoughtfully arranged as the first time. Traveling with my dog can sometimes be a challenge, but Emily makes it so easy and welcoming. The space is not only pet-friendly, but genuinely pet loved—my pup settled in right away. Having a quiet, cozy spot where we both felt comfortable, which made the whole trip stress-free. Emily is a fantastic host—kind, responsive, and clearly dedicated to making her guests feel at home. I’m so grateful to have found such a reliable and relaxing place to return to, and I’ll definitely be back again. Highly recommend to solo travelers (especially with dogs!) looking for a peaceful getaway.

The Tuberose Suite
We had a great time during our stay! The place was clean and as described including all amenities. They fireplace was beautifully prepared! The host was quick to respond, flexible with the check in times and offered fantastic suggestions for trips in the area. We can highly recommend!

Bluemont Escape:Walk to Bears Den; Bear Chase Brew
We absolutely loved our stay here! It was super clean and very spacious! Amanda was a very accommodating host and I would definitely recommend this place!

Trailside Chalet (A storybook chalet with hot tub)
JoAnne's place was truly lovely. She took great care to make us feel at home and added in little touches, like welcome snacks and bathrobes, to make us feel welcome. She truly cared about our comfort. The home is adorable and extremely comfortable in a beautiful, serene wooded setting. It's access to the W&OD trail cannot be beat! My mother absolutely loved her daily visits with Meister the Cat and we enjoyed sipping coffee on the front porch while soaking in the sounds of nature. Thank you, JoAnne!

Peggy's Guest Hideaway
Better than what was expected from the moment we pulled into the driveway, walked down a very inviting path to the front door, and then when we walked into such a pleasant spot. Immediately felt a sense of “we’re in the right place”! Comfortable vibes were felt instantly! The property was perfect, not just because of where it’s situated, but also how meticulously it was planned out and taken care of and maintained. If you have a pup, or two, as in our case, this is for sure a great booking. Our two loved the walks around the property each and every time they had to go out, nighttime and daytime. When returning to SWPA for visits in the future, we can only see ourselves staying at this location. Absolutely FIVE STARS!

The Hidden Tree
My wife and I have stayed here before and will absolutely stay again! Fantastic location and Christian is one of the best hosts!

Riverfront Oasis with Mountain Views, Near Town
Loved our stay! We were here from DC mainly to hike and relax and the space was perfect for both! Location is close to the north entrance of Shenandoah National Park which was wonderful. We cooked most meals in the unit and it was well equipped for basic meals. Beds were comfy, AC/heaters worked great, and the views were spectacular. Host was lovely and quick to respond. Would definitely stay again!
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- Seven Springs Mountain Resort
- Fallingwater
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