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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Top Guest favourite
Guest suite in Woodstock
4.98 out of 5 average rating, 221 reviews

Our Retreat -in a peaceful setting.

Private- apartment in the lower level of our house. House in a rural setting- you may spot white tail deer or other wildlife.Enjoy the peaceful tranquil setting.We are within 5 minutes by car to Rte 70 and shopping centers. Our space isn't childproof. Workout equipment available for use at your own risk. We control the HVAC and will adjust as requested. May not be suitable for those with mobility issues due to the walk to the entrance. Non smoking. We aren't set up for heavy cooking. No stove.

Top 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, 139 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 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, 207 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 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
4.93 out of 5 average rating, 110 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.

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, 163 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 favourite
The exterior of a red brick building is shown, featuring a striking peaked roof and multiple windows. A shaded porch is visible at the entrance, adorned with potted plants. Lush greenery surrounds the property, and a gravel path leads up to the structure.
Farm stay in Leesburg
5 out of 5 average rating, 130 reviews

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

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, 147 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!

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, 120 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.

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, 135 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!

Guest favourite
A welcoming living area features a dark sectional couch adorned with colorful cushions. A low coffee table occupies the center, complemented by a cozy accent chair. Natural light enters through two windows with red curtains, creating a comfortable space for relaxation.
Apartment in Fulton
4.96 out of 5 average rating, 100 reviews

Family Vacation Home Base

Your entire family will truly enjoy the convenient access to a wealth of attractions from our centrally located home! This prime spot makes it easy to plan exciting day trips to vibrant cities such as Washington, DC, Baltimore, and Annapolis, as well as historical sites like Gettysburg. If you love the outdoors, you'll also find numerous beautiful parks and scenic hiking trails nearby, perfect for exploring nature and creating lasting memories.

Top Guest favourite
A tranquil pool area is showcased at dusk, with soft purple lighting illuminating the water. Lounge chairs line the poolside, and trees surround the space, creating a calm and serene environment. The moon is visible in the clear sky, enhancing the peaceful ambiance.
Tent in Westminster
4.98 out of 5 average rating, 100 reviews

Rest and Recharge Retreat

We have a new larger tent for 2026! Queen size bed. We have also added a sauna to our retreat. Rest and recharge at this beautifully landscaped glamping retreat. Enjoy quiet moments of zen in the meditation garden, awake to the birds and butterflies, float the afternoon away in the pool or enjoy stargazing in the hot tub at night. We are set up for a quiet retreat for 2 people. Additional guests must be approved in advance. No parties!

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, 153 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 holiday rentals

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