Guesthouse vacation rentals in Western Maryland

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Western Maryland guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Two chairs are positioned near a campfire ring on a grassy area, surrounded by trees. A gently sloping hill leads down to a pond, with a wooden fence visible in the distance. Sunlight filters through the leaves, creating a shaded and inviting space.
Guesthouse in Purcellville
4.81 out of 5 average rating, 275 reviews

Barn Apartment in VA Wine Country

CodyRating, 5 stars2 months 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!
A peaceful view of the Potomac River is framed by trees and greenery. A small staircase leads down to a wooden dock, adorned with planters filled with flowers. A motorboat can be seen gliding across the water, surrounded by lush hills in the background.
Guesthouse in Harpers Ferry
4.83 out of 5 average rating, 157 reviews

Riverkeeper Inn

SergioRating, 5 stars2 months ago
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
Top guest favorite
A single-story cottage is nestled among tall trees, with a grassy area in the foreground. The exterior is light-colored with contrasting dark shutters. A welcoming front porch is visible, adorned with potted plants, while a grill is positioned nearby, providing a cozy outdoor space.
Guesthouse in Aspers
4.92 out of 5 average rating, 396 reviews

Cottage on our horse farm

FrancisRating, 5 stars6 days ago
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
A kitchenette is displayed against a soft green wall, featuring white cabinetry and a granite countertop. A coffee maker and utensils are arranged on the counter. A single comfortable armchair sits nearby, enhancing the cozy feel of the space.
Guesthouse in Round Hill Village
4.79 out of 5 average rating, 450 reviews

Private detached garage suite

RitaRating, 5 stars1 month ago
Had a great stay. Would recommend to others.
Superhost
The in-law house exterior is shown, featuring a light green façade with multiple windows. A wooden deck is visible at the entrance, with stairs leading to a landscaped yard adorned with flower beds and shrubs. The area is surrounded by trees, providing a serene environment.
Guesthouse in Herndon
4.76 out of 5 average rating, 220 reviews

Historic Herndon In-law house, kitchen. By IAD.

Mary BernadetteRating, 5 stars1 month ago
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
Top guest favorite
A charming brick cottage is presented with a bold red door. Two large windows flank the entrance, allowing natural light to illuminate the interior. The structure is framed by lush greenery and landscaping, contributing to a welcoming exterior in a quiet neighborhood setting.
Guesthouse in Leesburg
4.96 out of 5 average rating, 554 reviews

CozyLeesburgCottage-Private Home Downtown Leesburg

NatashaRating, 5 stars4 weeks ago
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!
Superhost
A spacious bedroom is presented with a comfortable bed draped in neutral bedding and decorative pillows. A window allows natural light to illuminate the room, while a small side table holds a lamp. Soft area rugs add warmth to the wood floor.
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 favorite
The exterior of a cozy brick building is framed by lush greenery and trees. A small patio area features two chairs, surrounded by freshly mulched beds with low shrubs. The building's porch is screened, offering a welcoming entrance.
Guesthouse in Front Royal
4.89 out of 5 average rating, 261 reviews

"Cabbin" at Mountain Home B&B

MatthewRating, 5 stars8 months ago
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

Top guest favorite
The exterior of the studio loft features a red wooden facade with white trim and a steeply pitched roof. Two French doors provide entry, flanked by wooden steps leading to a broad landing. An air conditioning unit is visible on the left side.
Guesthouse in Round Hill Village
4.98 out of 5 average rating, 42 reviews

Wine Country Loft

HeatherRating, 5 stars3 weeks ago
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.
Top guest favorite
A welcoming entryway features a covered porch with two rocking chairs positioned on a concrete path. The front door is framed by two large windows, showcasing a panoramic view of the surrounding hills and fields in the distance.
Guesthouse in Stephens City
5 out of 5 average rating, 17 reviews

Ventura Cottage: 360-views/HotTub/4 acres/Gym

JosetteRating, 5 stars2 months ago
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.
Guest favorite
The entrance showcases a green front door framed by two topiary plants in black pots. The spacious, covered porch features a light-colored concrete floor and a wood post, contributing to the inviting appearance of the home.
Guesthouse in Round Hill Village
5 out of 5 average rating, 13 reviews

The Cottage

NelloRating, 5 stars1 month ago
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.
Top guest favorite
A charming cottage exterior is presented, featuring white siding and a metal roof. Lush greenery surrounds the entrance, accenting the inviting appeal. The front door is partially visible, framed by natural landscaping, providing a glimpse of the tranquil setting.
Guesthouse in The Plains
4.99 out of 5 average rating, 72 reviews

A lovely cottage in The Plains, Virginia

HeatherRating, 5 stars1 week ago
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.
Top guest favorite
The recently renovated stone cottage features rustic charm with a modern metal roof. Large windows invite natural light, and the outdoor patio area is equipped with seating and an umbrella for shade, surrounded by greenery and trees.
Guesthouse in Middleburg
5 out of 5 average rating, 85 reviews

18th Century Middleburg Cottage

BeverlyRating, 5 stars3 weeks ago
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.
Guest favorite
A colorful graphic welcomes guests to the Woodstock Hippie House. Swirling pastel patterns fill the background, complemented by whimsical mushroom illustrations. A cheerful smiley face is prominently displayed in the center, embodying a retro vibe and an inviting atmosphere for visitors.
Guesthouse in Woodstock
4.97 out of 5 average rating, 30 reviews

The Woodstock (VA) Hippie House

JenniferRating, 5 stars1 week ago
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.
Top guest favorite
A serene lake scene features a charming guest house and gazebo set against a backdrop of lush greenery. The water reflects the clear blue sky and gentle hills, creating a tranquil setting. The spacious lawn provides ample area for outdoor activities.
Guesthouse in Clear Spring
5 out of 5 average rating, 10 reviews

Private Lake House in western MD

JoshuaRating, 5 stars4 months ago
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
Top guest favorite
A cozy living area features a day bed adorned with decorative pillows, complemented by a large area rug. A small dining table for two is positioned nearby, with a light source illuminating the space. Decorative wall art and a window dressed with curtains add to the charm.
Guesthouse in Woodstock
4.96 out of 5 average rating, 140 reviews

Cozy cottage nestled on 8 acres with mountain view

ZachRating, 5 stars3 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 washer and dryer

Top guest favorite
Guesthouse in Bluemont
4.99 out of 5 average rating, 359 reviews

Skyhorse Retreat Guest House

TerriRating, 5 stars1 month ago
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
Guest favorite
A large garage with three dark doors is shown beneath a slate grey roof. The exterior is finished in light-colored siding, complemented by several windows above the garage doors. A welcoming front porch is greeted by a neatly arranged wreath on the door.
Guesthouse in Purcellville
4.94 out of 5 average rating, 86 reviews

The Nest on Nixon Road

CassandraRating, 5 stars6 days ago
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.
Guest favorite
A wooden bridge spanning a small creek is surrounded by lush greenery. The bridge features a simple rail design and sits on stone supports, offering access across the natural landscape. Diverse plant life grows abundantly around the area, contributing to a serene forest atmosphere.
Guesthouse in Lovettsville
4.95 out of 5 average rating, 20 reviews

The Tuberose Suite

PeerRating, 5 stars3 weeks ago
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!
Guest favorite
The charming exterior of the guest house is showcased, featuring a manicured garden with colorful flowers. A small dining set is positioned by the entrance, complemented by a grill nearby. Large windows reflect natural light, inviting views of the surrounding landscape.
Guesthouse in Bluemont
4.99 out of 5 average rating, 96 reviews

Bluemont Escape:Walk to Bears Den; Bear Chase Brew

LilyRating, 5 stars2 weeks ago
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!
Top guest favorite
The chalet is nestled among snow-covered trees, softly illuminated by string lights along the roof eaves. Pathway lights lead to a patio area with table seating, enhancing the serene winter landscape.
Guesthouse in Hamilton
4.99 out of 5 average rating, 151 reviews

Trailside Chalet (A storybook chalet with hot tub)

HopeRating, 5 stars1 month ago
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!
Top guest favorite
A screened porch features four wicker chairs with red cushions arranged around a small glass table. Wooden flooring and a gentle view of the green yard beyond enhance the inviting space for relaxation.
Guesthouse in Connellsville
5 out of 5 average rating, 73 reviews

Peggy's Guest Hideaway

JoeRating, 5 stars2 weeks ago
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!
Top guest favorite
A modern kitchen is seen alongside a dining area and a comfortable living space. The kitchen features white cabinetry, a gas stove, and essential appliances. A dining table with minimalist decor is set for meals, while a spacious gray sectional sofa offers seating in the adjoining lounge.
Guesthouse in Cumberland
5 out of 5 average rating, 57 reviews

The Hidden Tree

AaronRating, 5 stars2 weeks ago
My wife and I have stayed here before and will absolutely stay again! Fantastic location and Christian is one of the best hosts!
Superhost
The riverbank is framed by lush trees, with calm water reflecting the greenery above. The scene captures a sense of tranquility and natural beauty, inviting outdoor activities such as fishing or kayaking along the serene Shenandoah River.
Guesthouse in Middletown
4.9 out of 5 average rating, 39 reviews

Riverfront Oasis with Mountain Views, Near Town

KimberlyRating, 5 stars2 months ago
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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