Holiday houses in Glenelg

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Top-rated holiday rentals in Glenelg

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

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Guest favourite

A modern kitchen features a large island with bar seating and granite countertops. Stainless steel appliances and a six-burner gas range are present. Soft natural light filters through a window, illuminating a cozy living area with a comfortable sofa and decorative accents.

Guest suite in Glenelg

4.98 out of 5 average rating, 141 reviews

Lovely guest house with gourmet kitchen & King bed

If you're looking for a quick getaway or a brewery hopping good time we offer that and everything in-between. Locally offerings include walking trails/ restaurants, and family farms. We are located between Washington D.C. and Baltimore. Only a short 45 minute drive to D.C., you can spend the day exploring the museums and sites that the Nations Capital has to offer. Baltimore is 25 minutes away. A great place to see the National Aquarium. You will love your relaxing stay here in this rural area

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Top Guest favourite

A spacious sleeping area features a king-sized bed with a light-colored, textured duvet and decorative pillows. Two stylish lamps provide warm illumination beside the bed. A decorative bench sits at the foot of the bed, with neatly folded linens displayed on top. Natural light enters through a window with wooden blinds.

Guest suite in Derwood

4.98 out of 5 average rating, 240 reviews

Cozy, Private Garden Apt in Derwood-La Belle Vie

Spacious one bedroom basement apartment. Private entrance, full bathroom and kitchenette all newly done. Freshly landscaped slate patio with garden and pond. The sound of running water provides a relaxing environment. Secluded back yard backs up to beautiful woods. 5 min away from bike trails. Large, open living space with sectional couch, and attached eating area with a table that can double as a work station. Centrally located in Montgomery County-approx 40 minutes from DC/Baltimore/Frederick.

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Guest favourite

The main living area features exposed wooden beams above and a cozy sofa adorned with decorative pillows. A small dining table with chairs is positioned near a window, and a charming side table displays a decorative item. Natural light fills the space, enhancing its inviting atmosphere.

Guesthouse in Glenwood

4.95 out of 5 average rating, 209 reviews

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

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Top Guest favourite

The bedroom features a spacious bed adorned with a patterned blanket and decorative pillows. A circular area rug adds warmth to the space. Surrounding wall art complements the vintage aesthetic, while table lamps provide soft lighting. A rocking chair and another seating option are positioned nearby.

Guesthouse in Ellicott City

4.94 out of 5 average rating, 124 reviews

Cozy Historic Guest House

Located in the heart of Old Ellicott City! This studio is warm, cozy and decorated with almost all vintage furnishings to pay tribute to the 1800s home. The space offers a well stocked bedroom, full bathroom and kitchenette. Relax on the patio or walk to the many cafes and shops on Main Street. Parking is included. The home is built into a hill so you will need to walk up a series of steps & stoned in the back from the parking area to enter. Due to this our home may not be ideal for everyone.

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Guest favourite

A spacious kitchen area is highlighted by dark wood cabinetry and a black countertop. Pendant lights hang above the counter, and light wood flooring leads towards an open living space. Decorative wall art featuring floral motifs is displayed on the yellow walls.

Guest suite in Highland

4.79 out of 5 average rating, 141 reviews

"The Whole First Floor is Yours" near Columbia, MD

Welcome to the American Dream! Our home is set in a picturesque suburban neighborhood of the nation's capital. On our first floor (2000 square feet), we have two separate rooms with three beds, two bathrooms, a private access, and a full complement of amenities just for you! we can have 6 quests in total! Our 1.6-acre yard is perfect for anything from a peaceful lounge to a pickup soccer game. If you have a family, or a group of friends, welcome! My home is also close to Merriweather concert!

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Guest favourite

The image depicts a small historic log cabin with white siding, surrounded by lush greenery and well-kept gardens. Nearby, a larger white building stands. The scene is set under a clear sky, with soft natural light illuminating the exterior.

Tiny home in Glenwood

4.89 out of 5 average rating, 165 reviews

Ellerslie cabin

Located in Glenwood, Maryland, Ellerslie is a 50 acre farm which dates back to 1763 with scenic views, fields of corn and a tranquil stocked pond. Nestled here is a small historic log cabin, built around 1810, that is charming and cozy. It has recently been restored and is equipped with all modern amenities, including a new stainless steel refrigerator and gas stove. The cabin is perfect for a business person who prefers staying in the country to a city setting or for a weekend getaway.

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Top Guest favourite

A scenic view showcases a charming cottage nestled in a serene landscape, with gentle rolling hills and a white fence encircling the property. Soft golden light from the setting sun highlights the trees and adds warmth to the surroundings, creating a peaceful rural atmosphere.

Guesthouse in Mount Airy

5.0 out of 5 average rating, 27 reviews

Gillis Carriage House 1 BR entire place pond view

Take a break and unwind at this peaceful oasis. This charming guest cottage is tucked away from the hustle and bustle, offering a quiet retreat to relax and recharge. Yet it's conveniently located less than 10 minutes from shopping, restaurants, and a major highway. Enjoy a cozy interior, peaceful surroundings, and easy access to everything you need. Whether you're here for a weekend getaway or an extended stay, this tranquil spot is the perfect place to slow down and feel at home.

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Guest favourite

The historic stone house features a large front porch with a railing and several steps leading to the entrance. Its facade includes multiple windows framed by red shutters, with a modern addition visible on one side. Lush green grass surrounds the house, adding to the rural setting.

Farm stay in Mount Airy

4.98 out of 5 average rating, 121 reviews

Poole House at Friendship Farm

Welcome to Poole House at Friendship Farm! Escape to the country at this historic stone house built in the 1700s. With accommodations for eight guests it is perfect for a getaway with friends and family, wedding parties and work retreats. The house received a meticulous restoration that includes all mechanical systems and a modern addition with a gourmet kitchen and master bedroom. The property also includes a three car garage as well as a restored smoke house and log cabin.

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Top Guest favourite

The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.

Cottage in Leesburg

4.92 out of 5 average rating, 404 reviews

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

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Guest favourite

A bright and airy bedroom features a spacious bed with a white quilt and an accent pillow. Natural light filters through two windows, illuminating the wood floor. A small dining table with chairs and a wall-mounted air conditioner add functionality to the cozy space.

Guesthouse in Woodbine

4.95 out of 5 average rating, 155 reviews

Garden Cottage

Located in a beautiful and peaceful part of Maryland our Garden Cottage offers a cute and cozy getaway. A perfect escape from the city, our cottage is nestled among some of Maryland's best farmers markets, breweries, wineries, and outdoor experiences while still being conveniently located near several small towns and Frederick, MD. If you’re looking for a longer stay but our calendar looks booked please reach out to us!

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Guest favourite

A historic home constructed from stone is situated amidst lush greenery. The house features a wraparound porch with white railings and several tall windows. A smaller stone building is visible in the foreground, surrounded by expansive lawns and trees.

Farm stay in Brookeville

4.89 out of 5 average rating, 36 reviews

Farmstay in a Historic Home

Enjoy relaxing in a peaceful historic home on a working 500 acre farm steeped in history. Hosted by farmers but central to Baltimore, Washington and Frederick. Across from Patuxent State Park. Enjoy hiking on the farm or in the park, fishing in the pond, fresh veggies from the garden, farm animals that amuse or read a book with your feet in the creek. Individual fun but well suited to small events of any ilk.

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Top Guest favourite

Aerial view of a spacious cottage surrounded by lush green pastures and woodlands. The property features a large, circular driveway and open lawn areas, with fields stretching into the distance. The landscape showcases a blend of farmland and natural surroundings.

Farm stay in Damascus

5.0 out of 5 average rating, 125 reviews

Large countryside escape

Large, sparkling-clean, light-filled cottage with peaceful views of grazing horses, swaying pastures and mountains all around. Oversized dine-in kitchen and gathering room allow for reconnection. Clean linens, comfortable beds and quiet, allow for great rest. Unwind, reconnect and recharge in this magical place minutes away from the hustle and bustle of Damascus and 45 minutes from downtown DC.

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