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Holiday rentals in Reisterstown

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Top-rated holiday rentals in Reisterstown

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Guest favourite
The historic brick building features a classic architectural style, with several evenly spaced windows and two prominent blue doors at the entrance. A pathway leads to the doorway, with a flag displayed on the left side. Lush greenery surrounds the property, creating a serene outdoor setting.
Flat in Monkton
4.95 out of 5 average rating, 175 reviews

The Fisherman's Lodge at the 1858 Monkton Hotel

Love the outdoors? Love to fish, hike, bike, kayak? All of the above? The Monkton Hotel is a registered landmark that sits on the NCR trail, which runs along the Gunpowder River, home for some of the best trout fly fishing in the country. This fully renovated apartment, themed the "Fisherman's Lodge", is on the second floor and has the latest amenities. Nothing in the area matches the charm, convenience and history. An electric bike store, tube rental and great cafe are all in the same building.

Top guest favourite
The open-concept living space features a combination of comfortable furniture, including two green chairs and a gray sofa. A wooden coffee table occupies the center of the room, surrounded by an area rug. A fireplace and bookshelves add warmth and character to the setting.
Flat in Sykesville
4.95 out of 5 average rating, 225 reviews

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

Top guest favourite
Home in Owings Mills
4.93 out of 5 average rating, 106 reviews

Garden Cottage: Dogs welcome | primary on main

Step into a storybook spring at Grandma’s House, a nostalgic home in Owings Mills. Enjoy blooming dogwoods, a fenced yard for pups, and nightly deer sightings on our 1/2 acre. Ideal for exploring trails, sports games, medical travel (primary on main for easy access), and grad. season. Features a private upstairs wing, fully stocked kitchen, fast Wi-Fi, and heritage charm 30 mins from Baltimore. Wegmans nearby. Restorative, cozy, dog friendly! Full AC, laundry & parking. Permit: RHR-2026-00248

Top guest favourite
A spacious bedroom features a wooden bed frame with a light-colored mattress, flanked by two minimalist wall sconces. Soft blue throws are neatly arranged on the bed. A large window allows natural light, complemented by warm wood flooring. A wooden console table displays modern amenities.
Flat in Baltimore
4.99 out of 5 average rating, 120 reviews

Private Serene Suite with Jacuzzi- Non Smoking

Escape to this serene in-law suite, an extension of the main house, in Baltimore’s safest & quietest area. Ideal for couples, it offers a private Jacuzzi, California king bed, large modern TV, and dedicated HVAC for comfort. The spacious sitting area and luxurious shower create a peaceful retreat. Walk to nearby shops and parks for added convenience. A Tesla charger is available upon request, ensuring convenience for electric vehicle owners. Perfect for a relaxing getaway or city visit.

Top guest favourite
An open layout is showcased with a spacious living area, featuring a comfortable sectional sofa and a coffee table. A smart TV is positioned on a stand, while a dining set is visible in the background. Natural light filters through the windows, illuminating the space.
Guest suite in Randallstown
4.99 out of 5 average rating, 140 reviews

Private Efficiency Suite ~ King Bed ~ Baltimore Co

Welcome to Hickory Roots Hideaway! A cozy yet spacious 750 sq ft efficiency guest suite situated on our picturesque 4 acre homestead! Great Wi-Fi and amenities make this a perfect getaway even if work and virtual school must continue. Enjoy a relaxing stay - you are welcome to explore our garden, shoot some hoops in our basketball court, or get to know our adorable farm animals! We are conveniently located with easy access to I-70, I-795, and just 30 minutes from downtown Baltimore!

Top guest favourite
A charming stone cottage features a red front door with black shutters framing the windows. A friendly dog stands on the stone path, surrounded by lush greenery. The staircase leading to the studio is visible on the right side, along with decorative elements of the owner's residence.
Guest house in Towson
4.99 out of 5 average rating, 293 reviews

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Top guest favourite
A bright living area is presented, featuring a grey sofa adjacent to a rich brown ottoman. A small kitchenette is visible with a stove and refrigerator, complemented by open shelving. Natural light enters through a skylight and windows adorned with blinds. A doorway leads to a bathroom.
Guest house in Owings Mills
4.96 out of 5 average rating, 136 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 favourite
An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.
Guest house in Annapolis
4.99 out of 5 average rating, 199 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Guest favourite
A spacious master suite features a king-size bed with a decorative canopy, flanked by nightstands. Two armchairs provide seating, and a woven area rug adds warmth. A mural depicting nature adorns the wall, while large windows allow natural light. An accessible doorway leads to the bathroom.
Farm stay in Cockeysville
4.94 out of 5 average rating, 120 reviews

Historic Gatehouse Master Suite

Discover the historic charm of Maryland's scenic horse country! Our Master Suite, part of a Tudor-style gatehouse on a country estate, offers luxury and convenience. Minutes from Hunt Valley and Baltimore, indulge in a Carrera marble bathroom, a private deck with sweeping views, a full-size tennis court, a refreshing pool, and more. Immerse yourself in elegance and history.

Guest favourite
An outdoor seating area features two vibrant red chairs placed on a mulch bed. A small table stands between the chairs, surrounded by greenery and decorative plants. A bright red door provides an inviting entrance, while a vintage wrought iron fence encloses the area for privacy.
Guest house in Catonsville
4.95 out of 5 average rating, 328 reviews

Fox Cottage *Pet Friendly*

Fox Cottage is a thoughtfully designed eclectic modern retreat nestled beside our beautifully preserved 115-year-old Victorian home. Tucked along a peaceful, wooded path, this private cottage offers the perfect balance of charm, comfort, and convenience — ideal for couples, professionals, concertgoers, and travelers bringing their furry companions.

Top guest favourite
A spacious bedroom features a large wooden sleigh bed dressed in a checked pattern. A chandelier hangs from the ceiling, illuminating the rustic wooden beams. A window with light curtains allows natural light to enter, while a round mirror rests against the wall near a side table.
Cabin in Upperco
4.93 out of 5 average rating, 137 reviews

The Guesthouse at Downey Family Farm

Cozy yet spacious renovated log cabin on our small farm in Maryland's picturesque countryside. Large bedrooms, two bathrooms, great Wi-Fi, and fully-equipped kitchen and washer/dryer make this a great place to stay with your family. The Guesthouse is conveniently located with easy access to I-795, and is 35 minutes from BWI Airport.

Top guest favourite
An open living area showcases high wooden beams and natural light from large windows. The space includes a rustic kitchen with a stove, a cozy seating area, and a staircase leading to a library above. A warm color palette and antique furnishings create a welcoming environment.
Flat in Reisterstown
4.97 out of 5 average rating, 125 reviews

Barn Apt on Tranquil Historic Farm--Amazing Views

Beautiful, spacious loft-style apartment in barn on historic farm 25 miles northwest of Baltimore. Quiet, lovely, and peaceful, surrounded on all sides by farmland in conservation. Perfect for a relaxing, tranquil getaway, but within easy commute to Baltimore metro area.

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