Guesthouse vacation rentals in Montgomery County

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Top-rated guesthouse rentals in Montgomery County

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

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Top guest favorite

An inviting living area features a white brick fireplace, providing warmth and focus. Two brown armchairs are positioned around a round table with decorative items. A doorway leads to a bright bedroom, illuminated by natural light, enhancing the cozy atmosphere of the space.

Guesthouse in Washington

4.92 out of 5 average rating, 103 reviews

Lovely one bedroom w/a fireplace & outdoor space

Unwind with the whole family in this stylish& serene retreat.location is unbeatable! Just steps from the RedLine train & multiple bus routes, getting around is effortless. Nearby, you’ll find Whole Foods, Wegmans, CVS, Target, a library, parks & great restaurants.This beautifully renovated apt is entirely private & sleeps 3, featuring a cozy bedroom with queen bed & a comfortable sofa bed. Enjoy a private entrance and an outdoor patio, perfect for relaxing. near Georgetown, national mall & more.

Superhost

The living area features a cozy sofa adorned with colorful pillows, complemented by a sleek coffee table. Natural light enters through large windows, while a spiral staircase leads to the loft. An inviting front door opens to the outdoor space, enhancing the overall ambiance.

Guesthouse in Rockville

4.87 out of 5 average rating, 223 reviews

Adorable private 1-bedroom place, close to metro

Adorable 1-bed guesthouse close to metro station.Features a cozy double bed, a pull-out sofa and chic kitchenette.Private outdoor space with comfy chairs and fire pit.Street parking available on adjacent street.We are a long walk, or a short bus ride (15 minute walk) to the WhiteFlint metro station. 0.8 miles to Pike&Rose with lots of restaurants and shopping malls.Experience D.C. and return to your private cozy home away from home! 10 min walk to the winding creek park with trails by the creek!

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

4.94 out of 5 average rating, 198 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

The living area features a comfortable blue sofa accompanied by a vibrant orange armchair. A glass coffee table sits atop a patterned rug. Artwork adorns the walls, and soft lighting enhances the inviting atmosphere. A modern kitchen with stainless steel appliances is visible in the background.

Guesthouse in Washington

4.96 out of 5 average rating, 71 reviews

Entire 2-BR house with a padio

Charming 2-bedroom guest house located in a very vibrant neighborhood in DC. Comfortably sleeps 3 people. It is conveniently located near many restaurants, bars, bodegas, and public transportation. It is only a few stops away from downtown DC and major landmarks such as The National Cathedral, The DC Zoo, The Monument, The Lincoln Memorial, The Jefferson Memorial, and a wide array of Smithsonian museums. it is just a walking / biking distance from Rock Creek Park for nature and hiking lovers

Guest favorite

A two-story accessory dwelling unit features a combination of brick and siding exterior, with large windows allowing natural light. A set of stairs leads to the entrance, and the surrounding area is shaded by trees, contributing to a tranquil outdoor setting.

Guesthouse in Washington

4.95 out of 5 average rating, 123 reviews

DC Treehouse - Charming, private 1-bdrm ADU in DC

Come to DC to work or play but stay here to relax. DC can be a busy, loud, fast-moving city at times, but the space we've cultivated here is a tranquil escape from the commotion without having to leave the city. This private 1 bedroom accessory dwelling unit has a full bathroom, full kitchen, laundry machines, desk/workspace, dining table, and small porch with table and chairs for a morning cup of coffee or evening cocktail surrounded by trees. We're hosts focused on hospitality, join us!

Top guest favorite

A bright and open living space features a striped sofa with a wooden coffee table and decorative wicker baskets. A dining area with modern chairs is complemented by a patterned wall art piece. Natural light streams in from the doorway, enhancing the inviting atmosphere.

Guesthouse in Herndon

4.94 out of 5 average rating, 143 reviews

Modern Sugarland Apt-Metro/IAD

Welcome to our stylish basement apartment, perfect for modern travelers. Whether you're here for work or leisure, this space has you covered. Situated minutes from the Metro, Airport, and major work centers. The apartment features a desk with dual monitors, keyboard, mouse, and 1GB internet. At night, relax in the plush king-size bed. A convertible futon couch with a 65-inch TV, awaits your binge-watching sessions. A washer/dryer and full kitchen, w/refrigerator and stove complete the space.

Top guest favorite

An inviting living space featuring a spacious L-shaped couch adorned with vibrant throw pillows. A glass dining table is positioned in the foreground, complemented by a bottle of rosé and two glasses. A modern kitchen with stainless steel appliances and bar seating can be seen in the background.

Guesthouse in Rockville

4.94 out of 5 average rating, 215 reviews

Modern Farmhouse Apartment. Close to Metro

Welcome to this beautiful and private 2 bed and 2 bath fully equipped apartment in a gorgeous modern farmhouse. Perfectly located in the City of Rockville. The apartment is in the basement of a newly constructed (2020) home. Completely separate with a private entrance and outdoor space. When you enter the home you will notice full natural light and high ceilings. No detail has been spared in the cozy 1000 sq ft apartment. From the full size laundry room to the soft close toilet seats.

Guest favorite

The pool area features a crystal-clear pool bordered by stone pavers and landscaped greenery. A pool house with large glass doors is visible in the background, accompanied by a defined hot tub and neatly arranged lounge chairs. Surrounding trees and bushes enhance the outdoor setting.

Guesthouse in Monrovia

4.96 out of 5 average rating, 164 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

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, 303 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.

Superhost

The exterior entrance showcases a brick façade with a stone pathway leading up to double glass doors. Lush greenery flanks both sides, enhancing the welcoming feel of the approach.

Guesthouse in Silver Spring

4.92 out of 5 average rating, 12 reviews

Cozy Main Level near Downtown

Welcome to our spacious main level home located just 0.3 miles from downtown Silver Spring. Ideal for families or groups. Our home is situated in a vibrant neighborhood close to downtown, offering easy access to restaurants, shops, and entertainment. Whether you're visiting for work or leisure, our space provides a comfortable retreat. Book your stay with us and experience the charm of Silver Spring from our inviting home!

Top guest favorite

A bright and airy bedroom features a spacious bed with a white quilt and an accent pillow. Natural light filters through two windows, illuminating the wood floor. A small dining table with chairs and a wall-mounted air conditioner add functionality to the cozy space.

Guesthouse in Woodbine

4.96 out of 5 average rating, 136 reviews

Garden Cottage

Located in a beautiful and peaceful part of Maryland our Garden Cottage offers a cute and cozy getaway. A perfect escape from the city, our cottage is nestled among some of Maryland's best farmers markets, breweries, wineries, and outdoor experiences while still being conveniently located near several small towns and Frederick, MD. If you’re looking for a longer stay but our calendar looks booked please reach out to us!

Top guest favorite

The entrance features a vibrant yellow door contrasting with a gray exterior. The door is flanked by two windows with decorative glass. A wooden ramp leads up to the door, providing accessible entry into the rental space.

Guesthouse in Takoma Park

4.94 out of 5 average rating, 179 reviews

Private, above-ground studio

This space was just renovated and now has its own private bathroom on the same level! The above-ground rental has a full bathroom, queen size bed and kitchenette (small fridge, microwave and coffee maker) making sure you have the basics needed for exploring the area. Keyless access makes for easy check in. Located on a quiet residential street, you’ll get the rest you need for your time working or exploring the area.