Holiday rentals in Damascus

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Top-rated holiday rentals in Damascus

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Superhost
A spacious living area features a cozy blue sofa with an attached ottoman. A full-size desk and a chair provide a dedicated workspace. The setting includes a kitchenette with a refrigerator and a microwave, complemented by a neutral carpet and tasteful wall art.
Apartment in Germantown
4.8 out of 5 average rating, 15 reviews

Cozy Downtown Studio Suite

Stylish one-bedroom private suite in the heart of Germantown, MD! Walk to the library, restaurants, grocery stores, offices, entertainment, gym, and scenic trails. Enjoy a spacious living area with a full-size desk, cozy sofa, and a 45” Smart TV with high-speed WiFi. The bedroom features a comfortable full bed, two large windows with green views, ample drawers, and a closet. The suite includes a full bathroom and an in-unit washer/dryer. Perfect for business travelers, couples, or solo guests!

Top guest favourite
A spacious farmhouse with a modern design is depicted, featuring a metal roof and multiple gabled windows. The property is surrounded by a green lawn, showcasing the natural landscape in the background under a soft sunset sky.
Farm stay in Laytonsville
4.98 out of 5 average rating, 62 reviews

The Lounge at The Stables of Rolling Ridge

The Lounge at The Stables of Rolling Ridge is a private, quiet, newly renovated apartment in the heart of a small town. Conveniently located on 77-acres of rolling farm land, our family invites you to unwind and relax away from the hustle and bustle of the DMV. The farm offers incredible sunsets, lush gardens with a gorgeous wooden pergola, and plenty of farm friends to keep you company! The Lounge is bright with a modern farmhouse feel and comes with all the essentials to make you feel at home!

Top guest favourite
The exterior of a spacious two-story house is presented, featuring a light brown façade, large windows, and decorative window shutters. A welcoming front porch is visible, adorned with potted greenery. A driveway leads to a closed garage, with a basketball hoop positioned nearby.
Flat in Germantown
4.94 out of 5 average rating, 110 reviews

Private/Cozy Lower Level Apt-Great for Long Stays

Private entrance to One-bedroom apartment with Queen Bed, Full Bath, Lounge, Kitchenette/Dinette and Pool/Billiard Room. Perks include Wifi, Cable TV, Air-conditioning & Heating, Keurig Coffee Maker, Toaster, Microwave and Refrigerator, Hair Dryer, and Iron with Ironing board. Awesome safe neighborhood on a cul-de-sac, great landscape with a quiet & serene backyard facing wild life conservation land blending into Seneca Park trail. Perfect for a jog, or just read, and watch the deer and birds.

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, 219 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
A spacious home theater area is depicted, featuring comfortable reclining chairs and a large flat-screen television mounted on a blue wall. A warm wooden floor enhances the inviting ambiance, complemented by a decorative area rug. Additional seating is provided with a trunk and a small side table.
Guest suite in Gaithersburg
5 out of 5 average rating, 10 reviews

Private Luxe Retreat w/ Theatre

Enjoy a private country getaway in this expansive lower-level light-filled suite, tucked beneath a serene wooded estate. With a private entrance, this well-appointed space features a cozy bedroom, full bath, and an inviting common area perfect for relaxing or working. You’ll love the bar & kitchenette w/ mini fridge, microwave, air fryer, keurig and quartz countertops. Unwind in the home theater, play pool or Pac-Man, or head outside to your patio with firepit, surrounded by trees & fresh air.

Top 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, 195 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
A bright living area is presented, featuring two armchairs and a sofa, arranged around a circular coffee table. Natural light floods in through four windows, accentuating the hardwood floors and a patterned rug adorned with starfish. Decorative plants add a touch of greenery to the space.
Home in Gaithersburg
4.94 out of 5 average rating, 34 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.

Top guest favourite
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.
Guest house in Woodbine
4.95 out of 5 average rating, 111 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
A modern two-story home is set against a lush backdrop of greenery. A well-maintained driveway leads up to the house, framed by soft garden lights. The stylish facade features large windows that allow warm light to emanate from within, creating an inviting atmosphere.
Home in Rockville
5 out of 5 average rating, 45 reviews

Luxury 5BR Getaway |Hot Tub, Game Room & Fire Pit

Rare 5BR/5BA 4200 sq ft estate just minutes from DC! Enjoy a chef’s kitchen, full game room, gym, 6-person hot tub, 2 fire pits, kids’ playground, EV charger, heated floors, and more. Parking for 8, private backyard, indoor/outdoor dining, and concierge grocery service. Perfect for families, long stays, and business trips. Walk to schools and top dining. Custom fridge, high-end essentials, and unmatched comfort await!

Top guest favourite
The living area features a spacious couch dressed in soft blankets, complemented by two armchairs and a dark coffee table. A flat-screen television rests on a media console, while large windows allow natural light to brighten the space, offering views of the surrounding landscape.
Home in Frederick
4.98 out of 5 average rating, 57 reviews

Sugarloaf Mountain Retreat- 300 Acre Estate

Welcome to Sugarloaf Retreat! This cozy one-bedroom, one-bathroom home on a 300-acre estate offers stunning views, a fully equipped chef's kitchen, and a plush king-sized bed. Relax on the patio under the stars after a day of adventure. Conveniently located near Sugarloaf Mountain trails, C&O Canal, golf clubs, roads for biking, and just a short drive from Downtown Frederick, it's the ideal luxury escape in nature.

Superhost
A bright and inviting guest room is featured with hardwood flooring. A spacious bed with white bedding is positioned against a wooden headboard. Natural light filters in through two window shades. A small desk, chair, and lamp are visible, providing a convenient workspace.
Guest suite in Gaithersburg
4.92 out of 5 average rating, 13 reviews

Fully equipped kitchen, and baby crib available

Brought to you by Ameridency: 1.7 miles from I-270, 4.7 miles from Germantown Soccerplex, 0.4 miles from Bowling alley, 1 mile from Kaiser Permanente, 4 miles from Shady Grove Hospital and Shady Grove Metro Station, 0.7 miles from the Gaithersburg MVA, 1.2 miles from the shopping center, 3.1 miles from Fitness centers, 3 minute walk from the RideOn bus stop (61, 74, 78), and minutes away from Tech Hub.

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, 113 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 Damascus holiday rentals

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