Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favorite
The exterior of the apartment complex is highlighted by lush greenery and mature trees, providing natural shade. A well-maintained lawn surrounds the building, and the brick façade adds a classic touch to the welcoming atmosphere.
Guest suite in Silver Spring
4.82 out of 5 average rating, 197 reviews

Spacious, Private Basement Apartment

Clean private walkout basement apartment with private bedroom (queen bed); plus folding twin bed for third guest, private full bathroom; kitchenette equipped with a fridge, Keurig coffee maker, cook-top, boiler, microwave, and toaster; spacious living room with fireplace equipped with TV (Netflix) and free WiFi. Dining table with two chairs. Basic kitchen utensils and silverware. Workspace: desk, swivel chair. The entrance path is sloping, may be difficult for guests with mobility challenges.

Top guest favorite
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, 225 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.

Top guest favorite
A modern kitchen features wooden cabinetry and a spacious granite island at its center. Stainless steel appliances, including a refrigerator and oven, are present. Pendant lights hang above the island, and a decorative rug lies on the floor, adding warmth to the space.
Apartment in Clarksville
4.88 out of 5 average rating, 140 reviews

1k+ sf Charm in Upscale SFH Suburban NH of DC Balt

Read our reviews! this clean, 1k+ sf & above-grade (thus having plenty of natural light) ground floor 2BR Apt w own entrance in safe & highly sought-after upscale SFH community. Super Fast Internet! In-unit full-size LG washer & dryer. Full-size modern kitchen with granite countertop & big island. 7 minutes walk 2 shopping plaza & modern Columbia Gym, 22min to DC Metro & 25min to Baltimore. Home away from home with amenities such as king-size bed for MBR, big vintage desks, breakfast station.

Top guest favorite
A spacious bedroom area features a king-size bed with neutral linens, accompanied by accent pillows and a throw. A modern sectional sofa is positioned nearby, and a wall-mounted flat-screen TV is visible. Soft lighting illuminates the room, creating a relaxed ambiance.
Guest suite in Silver Spring
4.92 out of 5 average rating, 277 reviews

Private guest suite in a newly remodeled home

We welcome you to a spacious and private basement apartment with its own entrance and self check-in. Get cozy with your guests in a space that has a bedroom with a king-size bed, an 85-inch smart TV, soft sectional , private toilet, bathroom and kitchenet, all in the same space. None of the amenities are shared. The fully-equipped kitchenet has everything you'll need to cook and warm your meals. Guest suite is the entire basement apartment which is a part of a bigger home where host lives.

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, 301 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
A bright living area is presented, featuring two armchairs and a sofa, arranged around a circular coffee table. Natural light floods in through four windows, accentuating the hardwood floors and a patterned rug adorned with starfish. Decorative plants add a touch of greenery to the space.
Home in Gaithersburg
4.95 out of 5 average rating, 39 reviews

Entire Modern & Cozy Private Basement w/Amenities

Relax in our private, secluded basement suite, complete with a private cozy bedroom, newly renovated full bathroom, kitchen, and private entrance. This clean, one-bedroom suite in Gaithersburg, MD, is conveniently located near - - Germantown (9 miles ) - Damascus(3 miles), - Clarksburg (6 miles), - Washington DC (33miles) -Shady Grove Metro - 16 miles It is perfect for both short stays and longer visits. You'll have full privacy while we reside in the upper two levels of the home.

Top guest favorite
Guest suite in Gaithersburg
5 out of 5 average rating, 9 reviews

Private Mini-Suite (Space NOT shared with Host)

Keeping it simple at this peaceful and centrally-located place. 1.7 miles from I-270, 4.7 miles from Germantown Soccerplex, 0.4 miles from Bowling alley, 1 mile from Kaiser Permanente, 4 miles from Shady Grove Hospital and Shady Grove Metro Station, 0.7 miles from the Gaithersburg MVA, 1.2 miles from the shopping center, 3.1 miles from Fitness centers, 3 minute walk from the RideOn bus stop (61, 74, 78), and minutes away from Tech Hub and pharmaceutical companies.

Guest favorite
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, 84 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.

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
4.78 out of 5 average rating, 129 reviews

The whole first floor is yours in MD Columbia

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 a spacious suite with two beds, two bathrooms, a private access, and a full complement of amenities just for you! we can have 4 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
4.96 out of 5 average rating, 122 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!

Top guest favorite
The living space features a large dark sofa with a chaise lounge, facing a mounted TV. A wooden dining table with four chairs is positioned nearby, complemented by a patterned area rug on the wooden floor. A wall clock and artwork add functional and aesthetic touches.
Guest suite in Silver Spring
5 out of 5 average rating, 39 reviews

Renovated private basement w/gym, bus to DC

2 miles from DC, easily accessible by public transportation. 0.2 mile walk to bus stop to Silver Spring metro, or less than a 2 mile drive to the metro! Quiet and safe neighborhood (use Blair HS as a reference for location). Comfortable, clean, new space- close to all the things the DMV has to offer. Queen bedroom with a workspace & fast Wi-Fi, and living space with giant couch. There is also a gym available.

Guest favorite
A modern kitchen and dining area features sleek cabinetry and stainless steel appliances. A large table with white chairs occupies the central space, illuminated by soft lighting. A unique pendant light hangs from the ceiling, adding a design element to the contemporary environment.
Apartment in Glenmont
4.82 out of 5 average rating, 106 reviews

Luxury 1 BR + Den Apartment (lower level)

Just 35 minutes from the White House and 3 minutes from the Metro, this smart micro-luxury apartment offers private parking, a sunny deck, and a peaceful backyard and a bathroom to die for. Walk to Glenmont Station and hop on the Red Line for direct access to D.C.’s iconic landmarks and museums. Luxury, convenience and comfort in one stylish stay.

Popular amenities for Highland vacation rentals

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  2. United States
  3. Maryland
  4. Howard County
  5. Highland