Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favorite
A welcoming living space features a modern sectional sofa adorned with patterned pillows and a sleek coffee table. Nearby, a dining area with a round table and chairs is complemented by natural light from a window. A stainless steel refrigerator and decorative artwork enhance the ambiance.
Apartment in Silver Spring
4.92 out of 5 average rating, 459 reviews

Escape to a Sunny Apartment in a Quiet D.C. Suburb

Living Room amenities include a Smart TV and an Amazon Fire TV Stick. Fully equipped kitchen and cooking essentials. Lovely patio with seating area and herb garden. Comfortable bed and quality linens. Keurig coffee maker with coffee and tea provided. You have your own private entrance and patio area on an entire different side of the house so your experience can be as private as you like. The entire apartment which includes: washer/dryer, fully equipped kitchen and patio area. Your host will be available for anything you need during your stay. My daughter/co-host, Bernadette, a young D.C. professional, can also answer any questions about the D.C. area, restaurants and other cool places to go. The apartment is in a quiet suburban neighborhood with easy access to the Washington area. It's a short walk to the FDA. Downtown Silver Spring is nearby, with its many restaurants, bars, Fillmore music venue, Ellsworth Dog Park, and a movie theater. The National Archives, University of Maryland College Park and UMUC are just few miles away. A Ride-On bus stop is located on the same block as the apartment. A Metro bus stop is 5 minute walk. Silver Spring Metro Station is about 4 miles away. There are a few parking garages at the Silver Spring Metro Station if you choose to drive there and then hop on the metro. Free parking on weekends and holidays at all Montgomery County Parking garages (some lots and street parking may require payment on Saturday). You could also Uber/Lyft to the metro station or all the way into the city (great option esp if you're splitting fare).

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, 218 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
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, 194 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.

Guest favorite
A well-appointed bedroom features a queen-sized bed with a decorative red and white patterned quilt. Two bedside lamps illuminate the space, and natural light filters through the window treatments. Light tones are complemented by wood flooring and a ceiling fan adds to the comfort.
Guest suite in Wheaton
4.9 out of 5 average rating, 82 reviews

Pleasant 1 BR Suite near DC & Recreational Parks

This adorable private suite is close to everything, making it easy to plan your visit. Love nature? Love the city? It is unique because it is next to a 500 acre park with world-class gardens, hiking, biking, and horseback riding. It is also one mile to the city's Metro. Within a 30-45 ish min metro ride, you can be in the center of Washington DC to enjoy the free Smithsonian Museums, monuments, site-seeing and international festivals. Kitchenette, updated bathroom, free street parking, Wifi

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, 268 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, 298 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.

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
4.94 out of 5 average rating, 33 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
Townhouse in Columbia
5 out of 5 average rating, 14 reviews

Cozy Cottage in Columbia

Escape to Cozy Cottage this fall. This two-bedroom, single-story townhome in Columbia's Harper's Choice Village is surrounded by scenic walking paths vibrant with autumn colors. The cottage features a fully equipped kitchen, laundry room, and a private, fenced yard for ultimate relaxation. It's conveniently located near the Village Center for dining and groceries. Enjoy one designated parking space and visitor parking. Experience the best of autumn in Columbia at Cozy Cottage.

Top guest favorite
A modern basement apartment showcases an open layout with a dining area featuring a black table and four chairs. A dark sofa is positioned against a gray wall, and art pieces provide colorful accents. Soft lighting enhances the spacious feel of the room.
Apartment in Wilde Lake
5 out of 5 average rating, 81 reviews

Cozy | 1BR Apartment

Nestled in the scenic village of Wilde Lake, this cozy apartment offers a perfect blend of natural beauty and modern aesthetics. Beautiful trails and abundant green spaces make the surrounding area ideal for outdoor exploration. Located within walking distance from Merriweather Pavilion, local eateries, and The Mall in Columbia making entertainment readily accessible. With both urban conveniences and natural serenity, this Airbnb is the perfect choice for your next stay.

Superhost
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
4.77 out of 5 average rating, 123 reviews

The whole first floor is yours in MD Columbia

Welcome to the American Dream! Our home(total 6000+ square feet) is set in a picturesque suburban neighborhood of the nation's capital. On our first floor, we have spacious two bedrooms(3 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, welcome!

Top guest favorite
A modern two-story home is set against a lush backdrop of greenery. A well-maintained driveway leads up to the house, framed by soft garden lights. The stylish facade features large windows that allow warm light to emanate from within, creating an inviting atmosphere.
Home in Rockville
5 out of 5 average rating, 45 reviews

Luxury 5BR Getaway |Hot Tub, Game Room & Fire Pit

Rare 5BR/5BA 4200 sq ft estate just minutes from DC! Enjoy a chef’s kitchen, full game room, gym, 6-person hot tub, 2 fire pits, kids’ playground, EV charger, heated floors, and more. Parking for 8, private backyard, indoor/outdoor dining, and concierge grocery service. Perfect for families, long stays, and business trips. Walk to schools and top dining. Custom fridge, high-end essentials, and unmatched comfort await!

Guest favorite
A well-lit kitchenette features light wooden cabinets with a dark countertop, stainless steel sink, and basic appliances. A stylish dining table set for two is positioned nearby. A decorative shelf displays plants and an elephant figurine on the wall, adding a subtle decorative touch.
Guest suite in Silver Spring
4.88 out of 5 average rating, 59 reviews

Private Studio in Silver Spring

Welcome to our cozy studio in Silver Spring, MD! Our private bathroom and kitchenette offer convenience and comfort. Relax with a 55-inch Roku TV, rest on a queen-size bed, and work or dine at our versatile table. Steps from local amenities, our studio is your perfect base for Silver Spring adventures.

Popular amenities for Highland vacation rentals

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