Holiday rentals in Derwood

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Top-rated holiday rentals in Derwood

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Top guest favourite
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, 235 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.

Guest favourite
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.
Guest house in Glenwood
4.95 out of 5 average rating, 203 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 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, 175 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 spacious family room features a curved sectional sofa in light fabric surrounding a glass-top coffee table. A television is mounted on the wall, while natural light streams through windows, illuminating a decorative cabinet and accent chair in the corner.
Guest house in Leesburg
4.99 out of 5 average rating, 113 reviews

Private 2 King BR, 1 BA Apartment Near Wineries!

Fox Farm Apartment is a private country retreat, located on 10 acres, on a quiet, private road. It has 2 king bedrooms, one bath, with incredible views (the sunsets are amazing) and filled with natural light. It has a private entrance w/ staircase to 2nd floor. The bath has a luxury shower and dual vanities. It has a full kitchen stocked with cookware, Direct TV, and large family room. Very close to Leesburg and local wineries and breweries. Linens and towels, soaps, shampoos are included.

Superhost
A comfortable brown sofa is placed against a softly textured wall featuring decorative wall hangings. Two pink cushions are positioned on the sofa. A small side table stands beside the sofa, illuminated by a modern, multi-armed lamp.
Townhouse in Gaithersburg
4.88 out of 5 average rating, 252 reviews

Cozy, clean 2 Bedrooms apartment!

The space is located on the lower level of a townhouse, with a private entrance from the street. 1 assigned parking & visitors spots. It is solely dedicated to hosting guests, small families on vacation, solo travelers for work, tourist. Another rental listing is located upstairs. Motion act camera outside the front door, please refrain of bringing more people than you booked. NO PARTIES ALLOWED, NO SOCIAL REUNIONS ALL GUEST MUST BE REGISTERED INTO THE AIRBNB SYSTEM BEFORE CHECKING IN

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, 108 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.

Top guest favourite
A historic cottage features a log exterior and a distinctive red metal roof. Surrounded by lush greenery and colorful flowers, the property is set back from the road, offering a peaceful rural aesthetic. The front porch provides outdoor space with views of the natural landscape.
Cabin in Waterford
4.97 out of 5 average rating, 102 reviews

The Weaver’s Cottage c. 1815

Welcome to The Weaver’s Cottage c. 1815! This unique and peaceful historic property has been lovingly restored to maintain its original period character while providing modern convenience. Located in historic Waterford, VA, a National Historic Landmark, and close to many farmer’s markets, wineries, breweries, distilleries, restaurants, antiquing, endless outdoor activities, and more, you won’t lack for fun local things to do! The history of the village itself deserves to be explored.

Top guest favourite
A treehouse is elevated among lush greenery, supported by sturdy wooden posts. A small deck extends from the entrance, leading to a spiral staircase. The exterior features dark blue siding and a metal roof, harmonizing with the surrounding forested environment.
Treehouse in Leesburg
4.96 out of 5 average rating, 441 reviews

Romantic Secluded Treehouse Stay in the Sky

Enjoy sounds of nature and view from our amazing treehouse nestled in the Poplar Trees surrounded by woods. Climb steep spiral staircase to a comfortable modern living area with kitchenette and another spiral staircase to a lovely bedroom with king size bed, bathroom and shower. Enjoy your morning coffee on side deck. During winter months you can see Sugarloaf Mountain in the distance. (Make sure to read the other details to note)booking a treehouse in a tree.

Guest favourite
The living area features warm wooden paneling and a cozy seating arrangement. A comfortable sofa is paired with a table, while a TV is positioned on a stand. Natural light streams through large windows, enhancing the spacious ambiance of the room.
Flat in Bethesda
4.75 out of 5 average rating, 421 reviews

May sale, full apt 10 mi from DC

You’ll stay in a cosy ground floor apartment in a single-family house, safe neighborhood, close to NIH, Cancer Institute, Sibley and Suburban hospitals, all airports, beltway, golf courses, historic sights; - Complete privacy, your own entrance, free parking; - Check-in/out 4 pm/11 am; - Well trained pets welcome, with pet fee; - Kitchen. Access to laundry upon request; - Two queen-size sleeping places. Please read the entire description before booking.

Top guest favourite
A modern living area features a sectional sofa in soft tones, complemented by a coffee table with decorative items. A large television is mounted on a textured wall, and a dining area with a table and chairs is visible in the background. Natural light enters through expansive glass doors.
Home in Oakton
4.97 out of 5 average rating, 158 reviews

Quiet Luxury Home - Modern - King - 20 Min from DC

Completely new renovations with an eye for details have created a space that feels like a custom built home. Made to provide you with a memorable luxury rental experience. Comfortable, bright, modern, unique and stylishly furnished mastering the mix of timeless elegance and modern simplicity. An open floor plan space that’s equally welcoming and sophisticated, incorporating natural elements, layered fabrics, and textures.

Top guest favourite
A cozy living area features a spacious sectional sofa adorned with patterned cushions. A round table is accompanied by wooden chairs, while a minimalist coffee table sits on a plush area rug. Natural light enters through multiple windows, highlighting the room's inviting design.
Apartment in Leesburg
4.94 out of 5 average rating, 265 reviews

Downtown 1 BR Condo Steps to Everything

Large private hideaway, tucked one block from the bustle of King Street. This renovated 2nd floor condo with vaulted ceilings is accessed by a separate secure entrance. Full kitchen includes a 2 top table, toaster, pots & pans, dinnerware, basic cooks tools & coffee maker. Queen size bed with luxury linens & private balcony. 1 full bath. W/D in unit. High Speed Internet. 1 Reserved off street parking space.

Top guest favourite
The living area features a sleek black sofa facing an orange accent wall. Two blue chairs are positioned nearby, complemented by a coffee table with a decorative tray. A large artwork adorns the wall above the seating, and natural light enters through a window, enhancing the space.
Guest house in Rockville
4.93 out of 5 average rating, 349 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.

Popular amenities for Derwood holiday rentals

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