Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favorite

An open-concept living area is presented, featuring a cozy sofa and comfortable chairs arranged around a coffee table. A large smart TV is placed on a wooden cabinet. The bright kitchen area, equipped with modern appliances, is visible in the background.

Home in Silver Spring

5 out of 5 average rating, 15 reviews

Comfy Corner in Silver Spring & Near DC

Discover comfort and convenience in our charming two-bedroom basement unit. Nestled in a niche neighbourhood, you'll enjoy the safety and serenity of the area, perfect for peaceful living. Just minutes away, you'll find a variety of stores, restaurants, and hospitals, making everyday errands a breeze. For nature lovers, the surroundings are ideal for relaxing walks, with lush greenery & beautiful trails. Enjoy two comfortable queen-sized beds, a spacious bathroom, ensuite laundry & free parking!

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, 112 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 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 River Hill

4.88 out of 5 average rating, 132 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! High-end 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

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.

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, 470 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, 292 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

5 out of 5 average rating, 24 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

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, 69 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, 69 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

4.95 out of 5 average rating, 43 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.

Superhost

A cozy living area is furnished with a sectional couch adorned with yellow accent pillows. A wooden coffee table sits in front of it. Natural light enters through the window, complemented by a plant on the windowsill. An indoor palm adds greenery to the space.

Guesthouse in Savage

4.94 out of 5 average rating, 35 reviews

The GreenHaus Oasis near Baltimore/DC/Annapolis

Our cozy 1 bedroom 1 bath guesthouse is a great base to explore three great cities: DC (30 min), Baltimore (20 min), and Annapolis (25 min). It is located in a residential neighborhood and is steps away from historic Savage Mill. It is home to several cute antique shops, restaurants, and running trails to explore. Laurel Race track (5 min) Ft. Meade (10 min) UMBC ( 15 min) BWI Airport (20 min)

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

4.87 out of 5 average rating, 60 reviews

Cozy Cottage in Dayton

Cozy cottage 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.