Holiday rentals in Damascus

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Top-rated holiday rentals in Damascus

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

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Guest favourite

A modern kitchen features a large island with bar seating and granite countertops. Stainless steel appliances and a six-burner gas range are present. Soft natural light filters through a window, illuminating a cozy living area with a comfortable sofa and decorative accents.

Guest suite in Glenelg

Lovely guest house with gourmet kitchen & King bed

If you're looking for a quick getaway or a brewery hopping good time we offer that and everything in-between. Locally offerings include walking trails/ restaurants, and family farms. We are located between Washington D.C. and Baltimore. Only a short 45 minute drive to D.C., you can spend the day exploring the museums and sites that the Nations Capital has to offer. Baltimore is 25 minutes away. A great place to see the National Aquarium. You will love your relaxing stay here in this rural area

LocationValueWifi

4.98 out of 5 average rating, 144 reviews

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

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.

LocationValueIndoor spaces

4.95 out of 5 average rating, 76 reviews

Guest favourite

The modern lakeside home is framed by lush trees, featuring multiple levels and large windows that allow natural light to fill the interiors. A gravel area with seating and a fire pit sits in the grassy yard, providing a cozy outdoor space for gatherings.

Home in Gaithersburg

DMV 4BR Luxury LakeHouse - GameRoom Firepit

Welcome home to a modern, luxurious, unique, extra RARE, and serene 4BR lakeside retreat with a lake in the backyard. Your relaxing haven in nature's embrace, yet near city buzz. Minutes to DC, NoVA, Baltimore, dining, and shopping. Enjoy the entire house, including 4 bedrooms, 4 full baths, 3 living/family rooms, a Game Room with an Arcade and pool & foosball tables, gym equipment, and, to top it off, a rooftop deck with lake views. Amenities abound. Have a great time with family.

FamilyLocationPets

4.91 out of 5 average rating, 79 reviews

Guest favourite

The historic stone house features a large front porch with a railing and several steps leading to the entrance. Its facade includes multiple windows framed by red shutters, with a modern addition visible on one side. Lush green grass surrounds the house, adding to the rural setting.

Farm stay in Mount Airy

Poole House at Friendship Farm

Welcome to Poole House at Friendship Farm! Escape to the country at this historic stone house built in the 1700s. With accommodations for eight guests it is perfect for a getaway with friends and family, wedding parties and work retreats. The house received a meticulous restoration that includes all mechanical systems and a modern addition with a gourmet kitchen and master bedroom. The property also includes a three car garage as well as a restored smoke house and log cabin.

LocationFamilyView

4.98 out of 5 average rating, 122 reviews

Top guest favourite

A charming white farmhouse is set against a backdrop of rolling hills, with a vibrant row of sunflowers blooming in the foreground. The open pasture offers a serene landscape, enhanced by the warm light of the setting sun casting a gentle glow.

Farm stay in Mount Airy

Sunsets from a Haven on a Hill

Come rest & relax in the high hill country of Mount Airy, MD. Find an oasis of beautiful views, rolling hills, open skies, and pastureland. This three-story farmhouse sits on one of the highest points in Mount Airy, MD with views of both the sunrise and the sunset. With an open kitchen plan, large family room, and beds to sleep 9, it’s a perfect place to gather family together for the holidays. Unwind, unplug, and connect with your loved ones in this beautiful farm setting.

LocationFamilyHiking

4.98 out of 5 average rating, 109 reviews

Guest favourite

The exterior of a two-story brick house is featured, with a spacious wrap-around porch. Lush shrubs and well-maintained landscaping frame the walkway leading to the front door, which is flanked by two large windows. A cloudy sky adds a serene backdrop.

Home in Mount Airy

Century Revival

Welcome to your perfect Mt. Airy getaway, where small-town charm meets comfort and convenience. Located in the heart of town and just minutes from I-70, this beautifully renovated 1910 home makes it easy to explore or unwind. Whether you’re here for a weekend escape, visiting family, or passing through, you’ll love the blend of historic character and modern updates. Enjoy your morning coffee on the wraparound porch or relax after a day out in this peaceful, inviting space.

ValueFamilyGetting around

4.97 out of 5 average rating, 38 reviews

Top guest favourite

Home in Mount Airy

Private sauna retreat with country views

Welcome to The Gathering Place, a private Mount Airy retreat designed for families and friends. Unwind in the infrared sauna, gather by the fireplace, enjoy the game room, or relax on the deck with peaceful country views. Sleeps 10 with 4 bedrooms and 3 baths. Ideal for wedding weekends, winery getaways, family visits and girls’ trips. Enjoy 1 GB Wi-Fi, a well-stocked kitchen, garage parking and no cleaning fee. Designed for gathering, not parties.

FamilyLocationCleanliness

4.99 out of 5 average rating, 87 reviews

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

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!

LocationFamilyView

4.95 out of 5 average rating, 164 reviews

Guest favourite

A historic home constructed from stone is situated amidst lush greenery. The house features a wraparound porch with white railings and several tall windows. A smaller stone building is visible in the foreground, surrounded by expansive lawns and trees.

Farm stay in Brookeville

Farmstay in a Historic Home

Enjoy relaxing in a peaceful historic home on a working 500 acre farm steeped in history. Hosted by farmers but central to Baltimore, Washington and Frederick. Across from Patuxent State Park. Enjoy hiking on the farm or in the park, fishing in the pond, fresh veggies from the garden, farm animals that amuse or read a book with your feet in the creek. Individual fun but well suited to small events of any ilk.

FamilyLocationSleep quality

4.89 out of 5 average rating, 38 reviews

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

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.

ValueFamilySleep quality

5.0 out of 5 average rating, 127 reviews

Superhost

A modern dining table is set for two, featuring dark placemats, plates, and wine glasses. Two wooden stools with metal legs are positioned at the table, and natural light filters through the nearby window, complementing the simple yet inviting setup.

Flat in Damascus

Apartment- 1BR/1BA with Kitchenette

Completely private 1 bed/1 bath unit with walkout entrance. Bright beautiful living area & kitchenette to make you feel at home. Close to I-270 tech corridor, Holy Cross Germantown Hosp, Clarksburg Premium Outlet , Kaiser and Rio Washingtonian Center. Commutable to major cities in the DMV (DC Maryland and Virginia) area. See approximate distance below. Book now, I'd love to host you!

LocationFamilyNearby

4.76 out of 5 average rating, 17 reviews

Top guest favourite

A modern kitchen is highlighted by a spacious island featuring dark cabinetry and a white countertop. Bright pendant lights hang overhead, illuminating the area. A bouquet of fresh flowers adds a touch of color, while an array of appliances is visible in the open shelving.

Farm stay in Ijamsville

Beyond Your Expectations Farm Stay

Escape to our historic farm stay, where charm meets modern comfort. Enjoy the gourmet kitchen, unwind on the magnificent patio with a huge fire pit, and indulge in the infrared sauna. Perfect for families and friends, with an adorable kid's playhouse and games. Interact with friendly animals, immerse yourself in serenity, and experience the ultimate getaway near Whiskey Creek Golf Course.

ValueFamilyWifi

4.96 out of 5 average rating, 328 reviews