Holiday rentals in Derwood

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Top-rated holiday rentals in Derwood

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

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Guest favourite
A spacious living area features a bright red couch, accent chairs, and a decorative area rug. Natural light enters through large windows beside glass doors that lead to an outdoor deck. Wall art adds color to the neutral walls, creating a relaxed and inviting environment.
Guest suite in Bethesda
4.86 out of 5 average rating, 162 reviews

The Den @ Glen - 1B1B w/ kitchen and private door

The house is in a quiet and safe neighborhood. You will have your own bedroom, bath room, spacious living, dining area and a kitchenette (no stove or oven) with a refrigerator, a coffee maker, a microwave, a small portable electric hot pad, plates, bowls, cups and utensils for simple cooking. You have your own entrance to the space. The kitchenette is the only shared space so the host can access the laundry room. Locks are installed in all other area of the ground floor to ensure your privacy.

Guest favourite
Guest house in Glenwood
4.95 out of 5 average rating, 204 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.

Top guest favourite
A modern two-story building features large windows allowing natural light to fill the space, showcasing a sleek garage door. The open living area is furnished with a comfortable sofa and accent decor, while a cozy bedroom showcases a spacious bed with minimalist design. The contemporary kitchen provides stainless steel appliances and ample storage.
Flat in Sterling
4.99 out of 5 average rating, 104 reviews

The Potomac Perch-Peaceful Cozy Family Apt

Step into a calming and contemporary haven. This thoughtfully designed one-bedroom apartment features a spacious bedroom with full bathroom , a modern full kitchen perfect for preparing your favorite meals, and comfortable living areas. The bright and airy layout, with its clean lines and tasteful decor, creates an inviting atmosphere for relaxation after a day of exploring. Nestled in a quiet and peaceful neighborhood along Broad Run Drive, you'll be just moments from the scenic Potomac River.

Top guest favourite
A charming red structure is nestled near a tranquil pond, surrounded by lush greenery and flowering plants. A windmill is visible in the background, complementing the rural landscape, while a gravel path leads toward the entrance of the building.
Farm stay in Lovettsville
4.99 out of 5 average rating, 269 reviews

‘Waterfront’ Farm Escape for Hikers & Wine Lovers

Feel refreshed when you stay in this rustic gem! The Springhouse is nestled in the rolling hills of Northern Virginia’s Wine Country! Originally constructed in the early 1800's, the structure was built over a natural spring that was used for refrigeration. Water from the spring maintains a constant cool temperature throughout the year while also filling a pond. The original stone well, channel and stone flooring are all intact for guests to explore and experience how our ancestors lived.

Guest favourite
The bedroom features a spacious bed with a dark blue and white patterned bedding set. Soft lighting is provided by two bedside lamps on dark wood nightstands. Natural light enters through a window, illuminating the neutral walls and carpeted floor.
Flat in Gaithersburg
4.93 out of 5 average rating, 176 reviews

Private Garden Suite Near Metro to DC + Parking

Private, serene 1-bedroom garden suite with its own entrance, designed specifically for work-friendly longer stays and comfortable living near Washington, DC. Fully equipped with a dedicated workspace/chair, high-speed Wi-Fi, kitchenette and in-unit laundry for routine and convenience. Free parking included. Easy Metro access to DC, major hospitals, sports venues, and family neighborhoods—offering a comfortable, pet-friendly, well-located home base for work, rest, and visiting loved ones.

Top guest favourite
A cozy living area features a large black sectional sofa and two red chairs, offering a comfortable seating arrangement. A sleek coffee table is centered on a plush area rug. A flat-screen TV is mounted on the wall, complemented by two stylish floor lamps providing soft illumination.
Home in Bethesda
4.98 out of 5 average rating, 221 reviews

Stylish Spacious Greentree Apartment

This 1,500 sq ft spacious luxury apartment is located in the lower level of a private custom home. NO SHARED HVAC. Sunny and light bedrooms with top-notch finishes and décor. Private entrance and walkway, covered porch, and free on-site parking for 2 cars. Prime Bethesda location: 1 mile to NIH and Naval Medical with public transportation just outside the front door. Bus 47 (free to ride) takes 10 minutes to Bethesda Metro station (Red-line) or in the opposite direction to Montgomery Mall.

Guest favourite
The two-story brick home is situated on a gently sloping lawn, surrounded by lush greenery and trees. White shutters adorn the windows, enhancing the classic facade. A well-defined pathway leads to the blue front door, inviting visitors into a warm and welcoming environment.
Home in Chevy Chase
4.96 out of 5 average rating, 109 reviews

Exclusive Home in Upscale Chevy Chase

You will love the secluded garden, near woods with deer and wildlife, the sunny kitchen with skylights, garden room, and large brick patio. Enjoy the 10-minute walk to Amazon Fresh, Starbucks and Einstein Bagels. One mile to Bethesda Metro; 1.5 miles to NIH, and Washington DC. Just1.8 miles to acclaimed restaurants in Bethesda and Kensington. 5G Wi-Fi, large workspaces. Centuries old trees. Self-check-in. Plentiful street parking. Only service dogs allowed / charged at $10 per day.

Guest favourite
Flat in Great Falls
4.96 out of 5 average rating, 120 reviews

Wooded Retreat in Great Falls

Escape to this wooded retreat in Great Falls, perfect for nature lovers and adventure seekers. This basement apartment boasts a dining area with sunlit windows showcasing vibrant forest views, a spacious living room, and a cozy bedroom. Enjoy easy access to hiking, biking, and outdoor fun in the parks just minutes away. Relax in the great outdoors experience the shops and dining in the nearby village. A perfect blend of nature and adventure awaits at this charming getaway.

Top guest favourite
The open living area features comfortable seating arranged around a circular table. Natural light floods the space through multiple windows, highlighting the light colors of the decor. Wood beams add a subtle architectural element, while a patterned rug anchors the seating area.
Home in Leesburg
5 out of 5 average rating, 198 reviews

Downtown Leesburg Cottage. Walk to everything!

Beautiful cottage in Downtown Leesburg! Walkable to all that Downtown has to offer! Across the street from the iconic Mom's Apple Pie and a short walk to restaurants, shopping, breweries and W&OD trail. Just a short drive to many local wineries, wedding venues, hiking and only 20 minutes from the Dulles Airport. Escape for the weekend or week and enjoy this beautiful 2 bedroom/1 bath home. Equipped with the essentials you need for a more than enjoyable stay!

Top guest favourite
Guest house in Woodbine
4.95 out of 5 average rating, 147 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 favourite
Guest house in Rockville
4.93 out of 5 average rating, 355 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.

Top guest favourite
Aerial view of a spacious cottage surrounded by lush green pastures and woodlands. The property features a large, circular driveway and open lawn areas, with fields stretching into the distance. The landscape showcases a blend of farmland and natural surroundings.
Farm stay in Damascus
5 out of 5 average rating, 122 reviews

Large countryside escape

Large, sparkling-clean, light-filled cottage with peaceful views of grazing horses, swaying pastures and mountains all around. Oversized dine-in kitchen and gathering room allow for reconnection. Clean linens, comfortable beds and quiet, allow for great rest. Unwind, reconnect and recharge in this magical place minutes away from the hustle and bustle of Damascus and 45 minutes from downtown DC.

Popular amenities for Derwood holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Montgomery County
  5. Derwood