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

4.98 out of 5 average rating, 144 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

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Superhost

A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.

Home in Severn

4.86 out of 5 average rating, 226 reviews

Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21

Relax at this spacious 4,125 sqft, top-quality home on 1 acre. This 7-bedroom, 2.5 bathroom home features a private pool, gym, sauna, a huge family room w/ 10 ft ceilings, & a 67" Smart TV. Enjoy the large 1st class chef's kitchen with all the cooking & serving supplies you will ever need. Enjoy the modern amenities, multiple workspaces, a wrap-around porch, fire pit, & grill. Ideal for family events, quiet getaways, sports teams, & business mtgs. The perfect getaway for large or small groups.

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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

4.91 out of 5 average rating, 69 reviews

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!

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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

4.79 out of 5 average rating, 152 reviews

"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!

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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

4.94 out of 5 average rating, 120 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

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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

4.9 out of 5 average rating, 156 reviews

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.

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Top guest favorite

A modern living area features a spacious sofa adorned with decorative pillows, facing a large 70" LG 4K HDR TV mounted on an accent wall. An electric fireplace below adds warmth, while stylish artwork and lighting enhance the contemporary design.

Guest suite in Silver Spring

4.98 out of 5 average rating, 145 reviews

Brand New Modern Guest Living Space

Welcome to this new beautifully designed guest living space. The space comes with a 70" LG 4K HDR TV in the living room that is paired with a full equipped Dolby Digital 5.1 surround system, an Electric Fireplace, a Highspeed internet, each room has a smart 4k tv. There is a fully equipped kitchen, dining area, living room with sofa, bathroom, and bedrooms with queen beds. The space has a very beautiful modern design. Less than a mile away from shopping centers, Fast foods and a hospital.

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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, 313 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.

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Top guest favorite

A cabin is nestled among tall trees, featuring a sloped lawn leading up to a covered porch. The exterior showcases a combination of brick and wood, with a sturdy chimney on one side. A winding driveway approaches the property, framed by natural stone.

Home in Ellicott City

4.94 out of 5 average rating, 54 reviews

Country cabin in Ellicott City

Relax at this cozy and peaceful cabin. Recently renovated and minutes from Patapsco State Park and Historic Ellicott City, you'll love the serenity of the surrounding nature while still close to civilization. Just a 15 minute drive to the airport and close to highways linking to Baltimore and DC. Enjoy peaceful walks along the scenic road which leads to the Patapsco river and ample hiking and biking trails. Expansive wooded property offers ample peace and quiet.

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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

4.96 out of 5 average rating, 105 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.

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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

4.9 out of 5 average rating, 84 reviews

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!

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Top guest favorite