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, 118 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 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, 191 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 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, 260 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, 295 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, 78 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 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

4.97 out of 5 average rating, 76 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 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

4.96 out of 5 average rating, 45 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.

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, 121 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, 43 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!

Top guest favorite

A striking wall art piece features a vibrant red rose contrasted against a muted black-and-white background of a wooden surface. The artwork is displayed in a multi-panel arrangement, adding a modern touch to the décor.

Guest suite in Jessup

4.93 out of 5 average rating, 76 reviews

In-Law/Guest Suite ~~ Red Rose Inn

Red Rose Inn Perfect for business travelers, students, or in between housing. Count on reliable internet and a quiet workspace. Minutes to Columbia, Ft. Meade, Merriweather Post Pavilion, Gateway Drive, NSA, Annapolis Junction, Baltimore, JHU APL, University of Maryland, NASA Goddard and DC. Forget your worries in this spacious and serene space.

Superhost

A cozy living space features a navy blue sofa adorned with patterned cushions. A small round dining table with two chairs is positioned nearby. On the walls, framed black-and-white photographs showcase iconic red double-decker buses, adding a touch of urban charm.

Apartment in Columbia

4.76 out of 5 average rating, 58 reviews

The Cardinal in the Woods

Forget your worries in this cozy apartment in a quiet suburban neighborhood attached to a single family home. Enjoy quick access to Baltimore, Washington DC, and Annapolis. Take advantage of the miles of walking trails throughout Columbia and a couple mile drive from both Merriweather Post Pavilion and old Ellicott City.

Top guest favorite

The exterior of a charming townhome displays a mix of brick and white siding. A covered porch is supported by classic columns, while flower beds filled with colorful blooms enhance the entrance. Lush greenery surrounds the pathway leading to the front door.

Townhouse in Columbia

5 out of 5 average rating, 11 reviews

Cozy Cottage in Columbia

Attending the Annapolis Powerboat Show? Stay at a newly remodeled, spacious end-unit townhome just 40 minutes away in Columbia’s Harper's Choice. Enjoy open living and dining areas, king and queen bedrooms with hardwood decor, a fenced backyard, charcoal BBQ, and nearby restaurants, shopping, and recreation.