Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favorite

Home in Silver Spring

4.83 out of 5 average rating, 12 reviews

Lovely 1bd1ba Basement Apartment

Beautiful basement apartment 1bd/1bath in peaceful Colesville neighborhood, Silver Spring, MD. It has additional full size bed in the living room. Has tidy kitchen, dining area, living area, Wi-Fi, TV, Washer & Dryer (optional & as prior agreement); Parking, off street Quite time, 10pm to 7am Off New Hampshire Ave, MD 20905 Rent -Basement only (access from the back side of the house) COVID 19- Please follow CDC guidelines. NOT ALLOWED, Pets, Smoking, Gatherings, Parities, Guest Furniture, mails

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

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, 212 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, 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

4.91 out of 5 average rating, 258 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.

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, 477 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, 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 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, 74 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

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

4.89 out of 5 average rating, 101 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.

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 Savage

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.

Guest favorite

A spacious sleeping area includes a full-sized bed dressed in a patterned bedspread. Two light-colored seating chairs flank the bed, with small tables and lamps positioned on either side. A white-brick fireplace decorates the wall, complemented by potted plants and framed artwork.

Apartment in Sykesville

4.83 out of 5 average rating, 395 reviews

Quiet Studio Basement Apartment

Welcome to my private studio apartment with a separate entrance and private bath. There is a mini fridge, microwave, toaster oven, coffee pot, tea, sugar, half and half. Bottled filtered water. Recently renovated bathroom, fresh towels, wash cloths and soap, shampoo and conditioner, sheets and bedspread. Iron and ironing board.

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

4.8 out of 5 average rating, 54 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.