Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Superhost

A fire pit is centrally positioned on a wooden table, featuring decorative stones and visible flames. Surrounding seating is provided by black metal chairs and a table, set against a wooden fence that offers privacy. The outdoor space is peaceful, ideal for relaxation.

Guest suite in Glenelg

4.99 out of 5 average rating, 111 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

Superhost

Guest suite in Derwood

4.98 out of 5 average rating, 200 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.

Superhost

A spacious basement apartment is showcased, featuring a fully-equipped kitchenet with modern appliances and a dining table positioned nearby. Natural light floods the area through glass doors leading to the outdoor space. A decorative plant adds a touch of greenery to the minimalist environment.

Guest suite in Silver Spring

4.93 out of 5 average rating, 245 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.

Superhost

An outdoor deck is featured, with a gray finish and wooden railings. Stairs lead down from the deck, surrounded by greenery and a wooden fence. Soft light filters through nearby trees, creating a serene atmosphere in the space.

Home in Wheaton

5 out of 5 average rating, 14 reviews

Cozy Secluded Private Entrance, Private Bathroom!

I'm pleased to share my latest design after a two year renovation project! This finished basement has been totally renovated and designed with lots of great amenities! It features secure parking, a private entrance, brand new kitchenette area and private bathroom, dedicated workspace, LOTS of windows for natural lighting, a blackout curtain in the bedroom, and the entire ceiling has been soundproofed! Extra soundproofing has been used in the bedroom for added comfort and enjoyment!

Superhost

An outdoor patio area is seen, featuring four metal chairs arranged around a circular stone surface. Lush green grass surrounds the patio, with a fenced yard visible in the background. The sun sets gently, casting warm light over the scene.

Home in Gaithersburg

5 out of 5 average rating, 23 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.

Superhost

A sleek, modern bathroom features a freestanding soaker tub complemented by a wooden tray. A rain shower is visible in a glass enclosure, with textured stone tile detailing on the wall. Shelves hold neatly arranged toiletries, enhancing the spa-like ambiance.

Guest suite in Silver Spring

4.96 out of 5 average rating, 81 reviews

Relaxing 1 bedroom private basement apartment

Welcome, it's time to relax! This newly finished apartment is ready to host a single looking to get away, a couple looking to take a break, or a small family ready to enjoy the DMV area. 2 minutes from the NW branch trail that leads to Brookside Gardens and 5 minutes from the metro station (red line). Whether you choose to stay in and relax in the spa-like soaker tub and rain shower, use the workspace with high speed wifi, or get out and enjoy the trails, this location has it all.

Superhost

A comfortable living area is depicted with a large gray sectional sofa adorned with patterned throw pillows. A small coffee table stands in front, situated on a vibrant blue and white patterned rug. A full-length mirror reflects natural light, enhancing the open space.

Townhouse in Columbia

5 out of 5 average rating, 7 reviews

Cozy Cottage in Columbia

Nestled in the Village of Harper's Choice and 1.6 miles within walking distance to the Merriweather District, which boasts a variety of restaurants, shopping, recreational activities and the arts. The end unit, in a townhome community, is newly remodeled with open floor concept for living and dining areas. King and Queen bedrooms are traditionally furnished in beautiful hardwood decor. Unit is large and spacious with fenced in backyard, Charcoal BBQ and dining areas.

Superhost

A concrete patio area is shown, featuring two outdoor chairs. Lush green grass surrounds the concrete, with trees and a small shed visible in the background. Bright sunlight illuminates the space, creating a peaceful outdoor setting.

Apartment in Fulton

4.97 out of 5 average rating, 65 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.

Superhost

A winding stone pathway is bordered by bright green grass and colorful shrubs. Large trees provide shade, creating a peaceful outdoor setting. The pathway leads towards a well-maintained brick facade, enhancing the inviting appearance of the home.

Guest suite in Columbia

4.95 out of 5 average rating, 42 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

Guesthouse in Spencerville

4.87 out of 5 average rating, 30 reviews

Adorable Guesthouse on Historic Farm.

Spring is upon us at Drayton! With excellent proximity to both Washington DC and Balitmore, enjoy peaceful respite in a lovely historic cottage (fully airconditioned) in Montgomery County, MD. Enjoy the grounds of Drayton Manor, built in 1834, boasting beautiful cherry trees, magnolias, massive oak and yew trees, as well as an inground swimming pool (seasonal), summer house, fire pit, and a children's playground.

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

4.86 out of 5 average rating, 57 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.

Superhost

A living area is presented with a black leather sectional sofa adorned with patterned cushions. A vibrant red and blue area rug complements the space. The room features large glass doors that lead to a wooded view, flanked by dark curtains. A fireplace sits in the corner.

Condo in Burtonsville

4.93 out of 5 average rating, 243 reviews

Rancho Relaxo! A Southwest styled Casita!

Hello! Welcome to "Rancho Relaxo" (Simpson's reference), our little Casita just north of Silver Spring Md! It is a newly renovated, fully furnished 2 bedroom, 1 bath condominium decorated in the Southwest spirit, in a quiet neighborhood centrally located between DC and Baltimore!

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Other great vacation rentals in Highland

Guest favorite

A decorative sign spelling 'home' is mounted on a white door. The letters feature a blend of black, yellow, and red, incorporating the colors of the Maryland state flag. The door displays a textured panel design, adding depth to the entryway.

Private room in Sykesville

4.91 out of 5 average rating, 114 reviews

Private room in sykesville with bathroom

MarinaRating, 5 stars2 weeks ago

This is the third time when my husband is having a long stay in Kristin’s place. The same as before the place was clean and convenient , Kris responsible and welcoming host. The cats are adorable.

Guest favorite

A secure white entrance door features a traditional round knob and a keyhole, accompanied by a black lockbox for key access. The lockbox includes a numeric keypad for entry, providing a convenient and safe method for accessing the space.

Home in North Laurel

4.93 out of 5 average rating, 61 reviews

Beautiful & serene environment

NinaRating, 5 stars1 week ago

Amazing stay all around ! Super comfy space and super clean! The only thing is that while the listing says “Entire home” it is just a seperate space basement, but a huge spacious one at that! Olu’s airbnb is definitely worth all the while!

The cozy kitchen area features a rustic wooden table with two matching chairs, illuminated by warm light from a lamp. A modern stainless steel refrigerator and gas stove are positioned against the log walls, complemented by a decorative rug that adds warmth to the space.

Tiny home in Glenwood

4.89 out of 5 average rating, 141 reviews

Ellerslie cabin

AliceRating, 5 stars2 weeks ago

Truly a tiny house, beautiful setting, well equipped. Lovely linens and towels. Host was helpful and quickly responsive to all communications. A convenient location for my trip.

Top guest favorite

A serene bedroom features a spacious bed with crisp white linens. Two bedside lamps provide soft lighting next to dark wooden nightstands. Decorative wall art adds a modern touch, while large windows are dressed in light curtains, allowing natural light to filter into the room.

Private room in Laurel

4.96 out of 5 average rating, 103 reviews

Beautiful master suite with private bath

DawnRating, 5 stars4 weeks ago

Great place. Just as described. Flavia and her husband were very kind.

Guest favorite

A spa is shown, featuring bubbling water and comfortable seating along the edges. The design includes built-in jets and a privacy fence. Steam rises gently from the surface, indicating the warmth maintained at a maximum of 104 degrees year-round.

Private room in Catonsville

4.9 out of 5 average rating, 369 reviews

Private Bedroom (GREEN) with Shared Bathroom

ZulieRating, 5 stars5 days ago

House was very cozy and had everything you’d need. The neighborhood is quiet and Patricia communicates really well. I’d highly recommend this house for solo travelers.

Guest favorite

A clear Brita pitcher is placed inside a refrigerator, containing filtered water. The pitcher features a white lid and a spout for easy pouring. The inside of the refrigerator appears clean and organized.

Private room in Glen Burnie

4.82 out of 5 average rating, 754 reviews

Room Near BWI & Baltimore NO Cleaning Fee!

TyRating, 5 stars2 weeks ago

ALL as advertised - which made it perfect for my 12-hour needs, being close to BWI for my 6 AM breakfast at Panera, rental car return, and easily making my 9 AM flight!

Guest favorite

A secure entry system is mounted on a wall, accompanied by a small potted plant on a wooden shelf. A black mailbox is positioned below, next to a red fire extinguisher. The mix of textures adds practicality to the entrance.

Private room in Rockville

4.91 out of 5 average rating, 190 reviews

Independent Self check in/out bedroom SFH basement

PeggyRating, 5 stars3 weeks ago

Another wonderful stay at Phong's! I'm always happy to see when his place is available and I snatch it up immediately. Safe neighborhood, very clean and all necessary amenities available with a responsive, conscientious host!

Top guest favorite