
Guesthouse holiday rentals in Western Maryland
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Top-rated Guesthouses in Western Maryland
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Family-Friendly guesthouses

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!

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

The Shady Bear Cabin
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.

Private Luxury Retreat Close to everything!
We had a great stay! Check in instructions were clear and the space was clean and well-kept. Check out was a breeze as well. Monica was always responsive and friendly.

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

Trillium Acres Guest House
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.

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!
Guesthouses with a patio

Wine Country Loft
I would definitely recommend this Air B&B. It was adorable and very neat and clean with everything and more. We all loved it!!

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.

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.

Shenandoah Valley cottage & private pool
Paige’s place was absolutely stunning! It was private, the pool was immaculate, the place was cozy, and she had everything you could possibly need inside. She was also a super responsive host. She gave us many great local recommendations and answered any questions we had within minutes!! We are already looking into booking again! We can’t recommend this stay enough!!
Guest house rentals with a washing machine 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.

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!

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.

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!

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!

Charming Guest House Bedford County PA
The place was nice and so was the host. We had good time but there were few things I didn’t know which was in Bedford country 15 min from there didn’t sell beer at local shops. Another thing was Walmart didn’t have grocery only other thing product. The owner lives next door. Other than that we had a great time it was a good place very clean and friendly host.

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
- Canaan Valley Resort & Conference Center
- Blackwater Falls State Park
- Idlewild & SoakZone
- Flight 93 National Memorial
- Timberline Mountain
- Hidden Valley Resort
- Ohiopyle State Park
- Wisp Resort
- Shawnee State Park
- Pikewood National Golf Club
- Bella Terra Vineyards
- White Grass
- Lakeview Golf Resort
- Lodestone Golf Course
- Laurel Mountain Ski Resort
- Canaan Valley Ski Resort
- Winter Experiences at The Peak
- Mountain Dragon Mazery Fine Honey Wine
- Warden Lake
- Clear Shade Creek