Vacation rentals in Glenelg

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Top-rated vacation rentals in Glenelg

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

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Guest favorite
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, 133 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

Guest favorite
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, 204 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.

Top guest favorite
An inviting family room features a pool table at its center, surrounded by comfortable seating and dining areas. Natural light illuminates the space through large doors leading to the deck. Ceiling fans and a warm color palette contribute to the open, relaxed atmosphere.
Home in Columbia
4.94 out of 5 average rating, 111 reviews

Rancher by Wash/Balt/Annap w/pool table, Kit, Deck

My Columbia House sits between Baltimore, Washington DC, and Annapolis, plus Historic Ellicott City, (county seat), is 8 miles close. The kid friendly neighborhood is central to Columbia village centers offering shops, restaurants, entertainment, lakes, hiking trails + more. Guests will enjoy FiOS Quantum data-multiple Laptop friendly work areas, 2 TVs and data jacks thru-out the home. See owners' favorites' list for local treats like Savage Mill, Ellicott City, or Merriweather Post Pavilion

Top guest favorite
The treehouse is elevated among the trees, featuring large windows that offer views of the surrounding forest. The exterior is constructed with dark wood shingles and is supported by sturdy stilts, blending seamlessly with the natural environment.
Treehouse in Waterford
5 out of 5 average rating, 262 reviews

Hummingbirds Hideaway Treehouse

Do not book on airbnb and ask for early arrival. experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun this slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please message us prior to booking

Guest favorite
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
4.88 out of 5 average rating, 156 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.

Top guest favorite
A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.
Guest suite in Harpers Ferry
4.99 out of 5 average rating, 288 reviews

Luxury Mountain Getaway: Sunsets, Wines & Views

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Top guest favorite
The two-story brick home is situated on a gently sloping lawn, surrounded by lush greenery and trees. White shutters adorn the windows, enhancing the classic facade. A well-defined pathway leads to the blue front door, inviting visitors into a warm and welcoming environment.
Home in Chevy Chase
4.96 out of 5 average rating, 109 reviews

Exclusive Home in Upscale Chevy Chase

You will love the secluded garden, near woods with deer and wildlife, the sunny kitchen with skylights, garden room, and large brick patio. Enjoy the 10-minute walk to Amazon Fresh, Starbucks and Einstein Bagels. One mile to Bethesda Metro; 1.5 miles to NIH, and Washington DC. Just1.8 miles to acclaimed restaurants in Bethesda and Kensington. 5G Wi-Fi, large workspaces. Centuries old trees. Self-check-in. Plentiful street parking. Only service dogs allowed / charged at $10 per day.

Top guest favorite
A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.
Home in Harpers Ferry
4.96 out of 5 average rating, 102 reviews

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

Top guest favorite
A wooden table is set with a bottle of Walnut Crest Cabernet Sauvignon and two etched wine glasses. A red apple rests in a dark, leather-like bowl, with a serene backdrop of green foliage visible through a screened window.
Guesthouse in Highland
4.98 out of 5 average rating, 308 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

Top guest favorite
The living area features a textured gray couch adorned with colorful pillows, complemented by a wooden armchair. A coffee table sits at the center, showcasing a decorative bowl. In the background, a fully equipped kitchen is visible, along with a dining area featuring tall stools.
Home in Ellicott City
4.94 out of 5 average rating, 112 reviews

Historic Hillside Cottage

Experience the charm of an 1800s home styled with modern amenities. This historic cottage is steps away from all that Historic Ellicott City has to offer. Spend the day exploring Main Street lined with restaurants and small businesses or go for a walk, hike, bike ride or swim in nearby Patapsco State Park. Perfect for guests in town for weddings, concerts or those that love history and nature. Centrally located with easy access to Columbia, Baltimore & Washington D.C.

Guest favorite
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, 132 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!

Top guest favorite
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, 145 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!

Popular amenities for Glenelg vacation rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Howard County
  5. Glenelg