Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Top 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

4.99 out of 5 average rating, 113 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

Top guest favorite

The exterior of a spacious two-story house is presented, featuring a light brown façade, large windows, and decorative window shutters. A welcoming front porch is visible, adorned with potted greenery. A driveway leads to a closed garage, with a basketball hoop positioned nearby.

Apartment in Germantown

4.94 out of 5 average rating, 109 reviews

Private/Cozy Lower Level Apt-Great for Long Stays

Private entrance to One-bedroom apartment with Queen Bed, Full Bath, Lounge, Kitchenette/Dinette and Pool/Billiard Room. Perks include Wifi, Cable TV, Air-conditioning & Heating, Keurig Coffee Maker, Toaster, Microwave and Refrigerator, Hair Dryer, and Iron with Ironing board. Awesome safe neighborhood on a cul-de-sac, great landscape with a quiet & serene backyard facing wild life conservation land blending into Seneca Park trail. Perfect for a jog, or just read, and watch the deer and birds.

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, 204 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, 187 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

4.93 out of 5 average rating, 98 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

Superhost

An airy interior is highlighted by wooden beams and natural light from multiple windows. A compact kitchen with blue cabinetry and white countertops is visible, alongside a cozy sitting area featuring a textured sofa and a small coffee table. A black ladder leads to the upper loft.

Tiny home in Silver Spring

4.83 out of 5 average rating, 472 reviews

★Cozy Tiny House★ Private and Quiet

Ever wanted to experience a real Tiny House? Here's your chance! This one sits at the back of an acre lot in Silver Spring. Close enough to visit DC or Baltimore but far away from all the noise. End of a quiet cul de sac in a beautiful neighborhood. Perfect to get away and relax. Sleeps 3 with a queen bed in the upper loft and a twin bed in the rear. Fully functional kitchen and bathroom with walk in shower. Mini fridge/freezer, conduction cook top stove, AC/Heat unit, hot water, and more!

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, 293 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 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 Columbia

5 out of 5 average rating, 71 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.

Top guest favorite

A spacious bedroom features a comfortable bed with a light quilt and two decorative pillows. A nightstand with a lamp sits beside the bed. A ceiling fan is overhead, and a closet with sliding doors is visible, offering ample storage space.

Guest suite in Columbia

4.88 out of 5 average rating, 64 reviews

QED Home Away From Home.

Beautiful ground level suite (fully handicap accessible with ramps) in private home located in a quiet cul-de-sac in Columbia, Maryland about 30 minutes drive to Baltimore and DC. Separate entrance with security system. Near many beautiful lakes in Columbia. Conveniently located near shopping centers, Columbia Mall, best public libraries in North America, hospital and community college. We can comfortably accommodate 5. Please contact me if more than 2 guest are expected,

Guest favorite

A cozy living area features two comfortable chairs, a coffee table, and a sleek fireplace. A television is placed on a wooden unit beside a small shelf. Soft lighting enhances the neutral color scheme and new flooring throughout the space.

Guest suite in Columbia

4.95 out of 5 average rating, 44 reviews

2 BR Lovely/Safest BSMT

Cozy, Deep wooded, very safe and peaceful 2 BR retreat Basement where you can get everything within 10 minutes drive. Whether you are professional needed a rest after long day work or just get away as long as you drive or Uber it’s perfect place. I have 8 & 10 years old boys and sometimes you will hear them or their foot steps upstairs when they are home playing. Normally they go to sleep at 8:30pm -7:30am. At school from 8:30-4:30pm.

Guest favorite

The exterior of a two-story townhouse is visible, featuring a red front door framed by large windows. Lush greenery and flower beds surround the entrance, complemented by a concrete walkway leading to the door. The setting is well-lit by natural sunlight.

Townhouse in Olney

4.91 out of 5 average rating, 98 reviews

Your vacation at perfect & cozy townhouse

Relax with the whole family at this peaceful place to stay. You will be close to your family! Enjoy a game of tennis or light the fireplace and enjoy it with a board game You will be next to the best shopping center across the street with everything you need three supermarkets, banks, restaurants, laundry, service, tjmax, etc. there is a playgroung ,tennis court, is a beautifully neighborhood to walk, Olney is a perfect family town.

Superhost

The exterior of the cottage is showcased, featuring a brick facade and neatly manicured bushes. A covered entryway provides sheltered access to the front door. The surrounding yard is landscaped with lush grass and a sparse tree line in the background.

Guesthouse in Dayton

4.82 out of 5 average rating, 61 reviews

Cozy Cottage in Dayton

Our cozy cottage (a spacious studio) is in a quiet and peaceful neighborhood. Perfect for relaxation with the whole family or couples getaway. Within walking distance to Big Branch Recreation Area. Close drive to Triadelphia Lake View Farm, gas stations, and restaurants. About 30 minutes drive to Baltimore/Washington International Thurgood Marshalls Airport and 21 minutes drive to the Mall in Columbia.