Vacation rentals in Highland

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Top-rated vacation rentals in Highland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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

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

ValueLocationLaundry

4.98 out of 5 average rating, 145 reviews

Guest favorite

A two-story apartment building is depicted with a light gray exterior and dark shutters. Outdoor steps lead to the upper entrance. A spacious driveway is visible in front of the garage doors, surrounded by green grass and trees in the background.

Guesthouse in Laurel

Cozy & Quiet 2 Bed Rm ADU Apart near DC&Baltimore

Get away for a relaxing weekend or short-term stay and Long term rental also available in this peaceful unique Garage Loft Apartment with parking and amenities all to yourself and whoever comes along with you! With a small patio to relax on and a vast backyard to roll around in, you can experience an unbothered stay only minutes away from a McDonalds, a Weis's grocery store, gas stations, various other stores just down the street. You'll want for little else but more time in this amazing Unit!

ValueFamilyAir conditioning

4.91 out of 5 average rating, 69 reviews

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

"The Whole First Floor is Yours" near Columbia, MD

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 two separate rooms with three 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, or a group of friends, welcome! My home is also close to Merriweather concert!

FamilyValueTV

4.79 out of 5 average rating, 152 reviews

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

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

LocationFamilyPool

4.94 out of 5 average rating, 120 reviews

Guest favorite

A green front door is adorned with a circular welcome sign, featuring a warm greeting on a decorative banner. The door's glass accents provide an inviting glimpse of the entryway.

Home in Laurel

Remedy Cottage

Welcome to Remedy Cottage, a place that holds deep sentimental significance for our family. It is a split foyer, two levels with steps leading in each direction from the foyer. It was built in 1978, every inch was renovated in 2022, featuring a brand new kitchen appliances. The interior boasts a modern farmhouse and minimalist design. This location is ideal for visitors to the nation's capital, the NSA, Andrews Air Force Base, and a short driving distance to three major airports in the area.

ValueFamilyCleanliness

4.9 out of 5 average rating, 156 reviews

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

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.

LocationValueGetting around

4.92 out of 5 average rating, 314 reviews

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

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.

ValueFamilyGrill

4.98 out of 5 average rating, 313 reviews

Top guest favorite

An outdoor patio area features a hot tub, a dining set, and a grill. A shaded seating area is furnished with cozy couches, while a colorful game board adds a playful element. Lush grass covers the ground, creating a welcoming space for relaxation and enjoyment.

Home in Silver Spring

Modern 3-Level Stay| Hot Tub | Game Room | Parking

Spacious 5BR home near D.C. with hot tub, fire pit, and game room—perfect for families or groups! Enjoy 3 levels of comfort, a full kitchen, fast Wi-Fi, smart TV, and self check-in. Relax in the private backyard, grill out, or unwind in the hot tub. Pet-friendly and sleeps 12 comfortably. Located in a quiet neighborhood just minutes from downtown Silver Spring and Washington, D.C. Free parking, kid-friendly, and ideal for work trips or weekend getaways. Book your stay today!

LocationValueNearby

4.99 out of 5 average rating, 289 reviews

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

Cozy | 1BR Apartment

Nestled in scenic 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.

LocationFamilyTV

4.99 out of 5 average rating, 103 reviews

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

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.

ValueFamilyHeating

4.96 out of 5 average rating, 106 reviews

Top guest favorite

The entrance of the apartment features a covered porch with a neatly arranged doorway. Lush greenery frames the entrance, including a bush and potted plants. A paved drive leads to the entrance, with fallen leaves scattered on the surface, adding a touch of seasonal charm.

Apartment in Laurel

The Rin’s Nest Cozy 2-Bedroom Retreat & Bonus Room

Tucked away just outside Columbia, Maryland, The Rin’s Nest is a peaceful retreat where you can relax and recharge. Thoughtfully decorated in soothing tones, this charming apartment offers comfort and convenience located near Merriweather Post Pavilion, BWI Airport, shopping, dining. Only a short drive to Baltimore and Washington, D.C.—perfect for day trips and city adventures. Comfort, convenience, and charm all in one place!

LocationFamilyRiver

4.91 out of 5 average rating, 85 reviews

Top guest favorite