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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Guest favorite

Guesthouse in Glenwood

4.94 out of 5 average rating, 161 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.

Apr 1 – 8

R3,341 ZAR per night

Superhost

Guesthouse in Herndon

4.77 out of 5 average rating, 203 reviews

Historic Herndon In-law house, kitchen. By IAD.

Entire in-law house w/ full kitchen and bathroom. Over 800 sqft. The house has a bedroom. You have the entire place to yourself and your family/friends. Keypad on the entrance so you can come and go whenever you please. Free parking. Verizon Fios TV, Gigabit WiFi Internet (speed varies). In-room climate control with central air and heat. -walk to downtown Herndon -close to FFX Parkway ~8 mins to Reston Town Center ~10 mins to Wiehle-Reston metro ~10 mins to Dulles Airport ~30 mins to Wash D.C.

Sep 24 – Oct 1

R3,963 ZAR per night

Guest favorite

Guesthouse in Clarksville

4.93 out of 5 average rating, 14 reviews

Unique guest house spa retreat

Kick back and relax in this calm, stylish space, central to amenities. Well connected to commuter routes. Located on a serene meadow in the heart of Clarksville, while giving you access to downtown Columbia, sport and fitness, fine dining, art and culture, music events, parks and hikes galore. Short distance to Fort Meade, NSA, NASA, Washington DC, Baltimore, historic Ellicott City, and Merriweather Post Pavilion. Fully independent guest house for privacy and convenience in a beautiful setting.

Sep 13 – 20

R2,717 ZAR per night

Guest favorite

Guesthouse in Washington

4.9 out of 5 average rating, 411 reviews

Ingraham Alley Inn - A Quiet & Cozy Micro House

Our microhouse in 16th St Heights is the perfect home base for exploring the city. We're close to Rock Creek Park, the many restaurants and coffee shops of Petworth and Columbia Heights, and just a short bus ride from the downtown tourist sites. 16th St Heights is worthy of a little exploration in its own right, with a fantastic farmers market, beloved local eateries like Moreland’s Tavern and Highlands Café, and miles of forested bike/jogging trails in Rock Creek Park just a short walk away.

Nov 2 – 9

R1,776 ZAR per night

Guest favorite

Guesthouse in Hyattsville

4.83 out of 5 average rating, 228 reviews

Small cabin style- 23 min commute to US Capitol!

This in-law suite is better defined as a small apt. attached to house; own entrance, bathroom, kitchen & free parking! Queen bed, clean sheets, towels, iron, board, kitchen pots, dining table, TV & more. It’s small but with all amenities necessary to live. If looking for a huge space, this will not be it. Good for single/couple cruising by the DMV on a BUDGET! -20 min walk to metro; off DC border, 18 min. drive to center of city. -Check in times on weekends may vary! Sat- 3pm & Sun- 5pm

Mar 20 – 27

R1,240 ZAR per night

Guest favorite

Guesthouse in Rockville

4.97 out of 5 average rating, 133 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.

Jun 19 – 26

R3,741 ZAR per night

Guest favorite

Guesthouse in Monrovia

4.95 out of 5 average rating, 110 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:)

Oct 11 – 18

R3,986 ZAR per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 264 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 and adjacent walking trails.

Oct 18 – 25

R2,216 ZAR per night

Superhost

Guesthouse in Silver Spring

4.8 out of 5 average rating, 116 reviews

*Contactless check-in/check-out Basement*

No contact basement suite. Self check-in/out ensures a no contact stay. Professionally cleaned after each guest checks out. Parking is safe and free on the street. There’s no kitchen but a breakfast station with coffee maker, microwave and refrigerator is in the suite. Silver Spring downtown is only 2 miles away with plenty of authentic restaurants and interesting local breweries. The short term residential license registration number : STR23-00099

Sep 19 – 26

R1,580 ZAR per night

Guest favorite

Guesthouse in Takoma Park

4.92 out of 5 average rating, 132 reviews

Newly renovated private rental - close to DC!

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.

Oct 8 – 15

R1,785 ZAR per night

Guest favorite

Guesthouse in Silver Spring

4.96 out of 5 average rating, 52 reviews

Modern, spacious basement apt w/private entrance

Enjoy a modern kitchen and dining area, dedicated work space and large bedroom with a huge walk-in closet & en-suite bathroom with a large standing shower. This open concept home gets lots of sunlight throughout the day. Perfect for a visit to the suburbs of DC. Kid-friendly: toddler bed & high chair available upon request. Playgrounds and parks in neighborhood Dogs ONLY: Dog park in neighborhood & open grass areas

Aug 19 – 26

R2,322 ZAR per night

Guest favorite

Guesthouse in Rockville

4.92 out of 5 average rating, 301 reviews

Historic Carriage House with 1BR Loft

Historic 1-1/5 story carriage house in the heart of Rockville, MD. Located at the back of our property (detached from our main residence)- guest parking, private entrance, and covered outdoor patio with furniture available upon request. Modern but cozy decor. Comfortably sleeps 2 in king size bed, room for an additional guest on living room futon. Short 0.7 mile walk to Rockville Metro and Town Center.

Jul 19 – 26

R2,445 ZAR per night