Guesthouse vacation rentals in Maryland

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Maryland

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A modern kitchen area showcases a wooden countertop with two stools, complemented by a colorful floral arrangement. In the background, a cozy sleeping area features a quilted bedspread. Natural light streams through multiple windows, illuminating the space.

Guesthouse in Annapolis

5 out of 5 average rating, 156 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Guest favorite

The guesthouse exterior presents a gray facade with a welcoming porch. Lush greenery, including manicured bushes and large trees, frames the entrance. A paved walkway leads to the door, surrounded by planters. The house stands under a clear blue sky, providing a serene setting.

Guesthouse in Middletown

4.95 out of 5 average rating, 282 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

Top guest favorite

A wooden dock extends over calm waters, featuring two adirondack chairs and a wooden bench. The serene landscape includes distant trees along the water's edge, creating an inviting atmosphere for relaxation.

Guesthouse in Cambridge

4.99 out of 5 average rating, 119 reviews

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Guest favorite

The image illustrates a charming tiny home nestled among trees, featuring a spacious bluestone patio with outdoor seating and a fire pit. In the background, a gas grill is positioned nearby. Lush green grass surrounds the area, creating a serene and inviting setting.

Guesthouse in Annapolis

4.96 out of 5 average rating, 178 reviews

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 102 reviews

Private Cottage on gated estate

Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapolis, and the Naval Academy. (4.7 miles to the main gate). We are on a private well but we have installed a state of the art water softener, filtration system, and a blue light bacteria zapper. Home and grounds are kid friendly offering amply outside play space and a multipurpose sports court. Third bedroom of home has a full-sized crib, baby gates, and a twin bed.

Top guest favorite

A private swimming pool is surrounded by a stone patio and greenery, creating a tranquil outdoor setting. Sunlight reflects off the clear blue water. A shaded area with a canopy is positioned at one end, while the pool area is enclosed by a wooden fence.

Guesthouse in Elk Mills

4.97 out of 5 average rating, 106 reviews

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

Guest favorite

An open layout showcases a dining area with a light-colored table set for six, adjacent to a cozy living space featuring a neutral-toned sofa and armchairs. A horse-themed artwork is displayed on the wall, while soft curtains frame the windows allowing natural light in.

Guesthouse in Elkton

4.92 out of 5 average rating, 135 reviews

Countryside-Stable House-Open Studio-Quiet for 2

Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

Guest favorite

The entrance to Fairwinds Cottage is highlighted by a white bench placed in front of a blue door. The cottage's exterior is adorned with vibrant flowering plants in window boxes, enhancing the welcoming atmosphere.

Guesthouse in Chesapeake City

5 out of 5 average rating, 163 reviews

High-End Cottage, Water View, Chesapeake City, MD

"Fairwinds Cottage" is a newly renovated coastal themed guest cottage with a water view on the quiet side of the canal in Chesapeake City, Maryland. Enjoy watching the ships pass through the canal, take a walk on the beautiful 17-mile Ben Cardin/Mike Castle Recreational Trail just steps from the house. Walk to Schaefer's Canal House for their amazing crab cakes and libations. Stay with us and learn why Chesapeake City was voted the #1 most charming town in Maryland in 2018.

Guest favorite

A white picket fence encircles a lush garden filled with vibrant flowers, including hydrangeas in soft pink and green hues. A winding path leads through the greenery, framed by tall trees that provide a natural canopy overhead.

Guesthouse in Oxford

4.95 out of 5 average rating, 111 reviews

The Nichols House Cottage

This lovely guest cottage is located in the historic district of Oxford, walkable to town attractions and restaurants. While the main house is a registered historical property built in the 19th century Victorian style, the guesthouse is charming and well decorated with modern comforts. The cottage is completely independent from the main house. Make this your special place for a romantic getaway at any season of the year.

Guest favorite

Two turquoise adirondack chairs are positioned on a gray concrete pad facing the water. A fire pit is placed nearby, with sandy shore and lush green grass surrounding the seating area. The peaceful waterfront includes a pier and distant homes under a partly cloudy sky.

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 331 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Top guest favorite

A quiet garden area features a stone pathway winding through vibrant greenery and blooming plants. The pathway is bordered by large shrubs and trees, creating a serene natural setting. A blue garden sign stands prominently among the foliage, adding a touch of color.

Guesthouse in Owings Mills

4.97 out of 5 average rating, 115 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Top guest favorite

A serene pond is surrounded by lush greenery, with tall trees forming a backdrop. The calm water reflects the blue sky, while vibrant plants border the shoreline. The scene conveys a peaceful natural environment, ideal for relaxation and enjoying the outdoors.

Guesthouse in Pocomoke City

4.95 out of 5 average rating, 142 reviews

2 Bedroom Apartment

Centrally located between Chincoteague Island and Ocean City, MD. This pet friendly two bedroom apartment which offers laundry and a spacious kitchen is only steps away from Shad Landing state park and Public Landing. This ground level guesthouse apartment is located 200 feet from our main house is on an over 12 acre partially wooded parcel. Plenty of privacy and room for boat trailer parking.

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What guests are saying

The Pig Shed Writer’s Retreat at Barter Lady Farm

4.88 out of 5 average rating, 329 reviews1 week ago

The Pig Shed was the perfect size for 2 humans and 3 dogs. It is cozy inside and the beautiful green fields that surround you fed my sole. It was peaceful with no urban or city lights. The perfect place to relax. There was plenty of places to walk our dogs. We stayed three nights and I wish we could have stayed two weeks.

Guesthouse in Westminster

What guests are saying

Cozy Lakeside Studio Retreat.

4.96 out of 5 average rating, 178 reviews3 weeks ago

We had a wonderful stay. Last night we kayaked on the lake and saw an osprey and this morning we went out on the deck to eat our breakfast and saw two otters playing! The private beach was super close and lovely. We had it to ourselves for hours. We will absolutely come back.

Guesthouse in Lusby

What guests are saying

High Water Guest House

5 out of 5 average rating, 14 reviews8 months ago

Marti's Airbnb is perfect in every way. From the start, Marti was very responsive & accommodating to my questions & requests. The Airbnb is very thoughtfully equipped with everything one might need for an enjoyable getaway (to include new inflatable paddle boards and kayaks). The furnishings are all upscale from the beds & linens to the kitchen equipment & gadgets. One really does feel at home. The neighborhood is lined with beautifully maintained historical homes. Restaurants are within walking distance - Snapper Waterfront Cafe - 2 min walk & Blue Ruin – 9 min walk. Jet skis and motorboats are available 3 miles away behind the Hyatt at Blackwater Adventures. The Hyatt has a wonderful Spa which offers day passes to enjoy the pools and the Spa's serenity areas & steam & saunas. Don't miss a visit to St Michael's! When we returned from Marti's Airbnb, my husband asked, "when are we going back?" I said, "to where?" He said, "to Marti's." I laughed as we just got home & unpacked.

Guesthouse in Cambridge

What guests are saying

Guest Cottage in Town

4.75 out of 5 average rating, 55 reviews4 weeks ago

The house suited all our needs and was very close to restaurants and retail. It was not fancy, but was very homey and comfortable. I felt like if we had any issues, we would get prompt and helpful response from our host. The stay met and exceeded all our expectations and we would recommend it to others.

Guesthouse in Great Mills

What guests are saying

Studio on the Bay.

4.96 out of 5 average rating, 108 reviews1 month ago

Studio on the Bay was perfect for our weekend get away. Jennifer and Joey were quick to respond to any questions we had and were top novk hosts. The view was amazing from the bedroom and you could see the sunrise over the bay. The bed was very comfortable and the bathroom/shower and closet area were very spacious. The kitchenette worked great for the small meals and we enjoyed the hot tub and fireplace outside. We were very close to fishing spots and enjoyed going out on Joey's charter Fish Taxi. We caught lots of fish and had a great day on the water. So if you are looking to fish check him out for sure. We plan to go back and would recommend the studio for your get away. Thank you Jennifer and Joey for sharing your studio and your welcoming hospitality!!

Guesthouse in Saint Leonard

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