Cottage holiday rentals in Western Maryland

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Top-rated cottage rentals in Western Maryland

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Top guest favourite
The exterior of a cozy two-story cottage is visible, showcasing a blend of stone and brick. A path of brick leads to a welcoming entrance, complemented by a nearby gentle stream and a red wooden bridge. Lush greenery surrounds the structure, creating a serene landscape.
Cottage in Strasburg
4.95 out of 5 average rating, 468 reviews

The Cottage at the Barb Farm

The Cottage at the Barb Farm is a cozy two story cottage nestled in the Shenandoah Valley on the historic Fisher's Hill Battlefield. The cottage was used as the summer kitchen in the civil war days. It was rebuilt in 1991 to the current cottage. There is lots of civil war history to discover, hiking trails, wineries, and breweries in the area. The town of Strasburg is about 15 minutes away. If you're looking for a weekend getaway or a relaxing vacation in the mountains, this is the perfect spot!

Top guest favourite
An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.
Cottage in Winchester
4.99 out of 5 average rating, 465 reviews

COZY+SEXY Private Country Escape! HOT TUB & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Guest favourite
A charming cottage is illuminated by string lights, creating a welcoming atmosphere. A fire pit surrounded by several chairs is visible, set against a backdrop of lush greenery. The large deck extends from the cottage, providing a spacious area to enjoy the outdoors.
Cottage in Mount Jackson
4.92 out of 5 average rating, 122 reviews

Hot Tub!, 2 Fire Pits, Huge Deck, Private orchard!

The home is an adorable cottage perfect for both a romantic getaway or a family/friends retreat. Enjoy views of the small orchard on the 3 acre wooded property from the large deck and two firepits. The Orchard Cottage is a great base to explore local wineries, hiking, and nearby Bryce Resort. Conveniently located 2 hrs from DC, 45 minutes from Harrisonburg, and only 12 minutes from Bayse/Bryce Ski Resort. Only a 15 min drive to I-81 to conveniently access all the Shenandoah Valley has to offer

Guest favourite
A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. A large island serves as a breakfast bar with four sturdy stools. Natural light floods in through a large window, providing scenic views of the surrounding landscape and illuminating the room's airy feel.
Cottage in Markham
4.94 out of 5 average rating, 182 reviews

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Guest favourite
Two classic wooden Adirondack chairs are positioned near the bank of a gently flowing stream. Lush greenery surrounds the area, with trees casting dappled sunlight on the water. A clear blue sky adds a serene backdrop, enhancing the peaceful atmosphere of the outdoor space.
Cottage in Waynesboro
4.95 out of 5 average rating, 131 reviews

Antietam Toll House~an historic waterfront cabin

The Antietam Toll House (@antietamtollhouse) is a renovated historic property circa 1800. Sitting on the bank-head of the Antietam stream, this cabin has it's own private fishing hole. Secluded, yet close to amenities and attractions, this property is the perfect place for an artist retreat, respite from the city or a base from which to explore local gems of the area. Wineries, Appalachian Trail, Antietam, Gettysburg battlefields, Ski Liberty, Catoctin , Cunningham Falls and more nearby.

Guest favourite
The exterior of a charming brown cottage is surrounded by lush green foliage. A spacious wooden deck with railing leads to the entrance, which is framed by white French doors. A red shade sail is positioned above the deck, adding a pop of color.
Cottage in Berkeley Springs
4.95 out of 5 average rating, 492 reviews

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

Hidden Hill is a renovated 1880’s cottage tucked away just above historic downtown Berkeley Springs. Xfinity high speed internet! Literally steps from spas, restaurants, art, antiques, and nightlife, this cottage also feels hidden just above downtown. Hidden Hill is a great spot to stay while enjoying everything Berkeley Springs has to offer. Explore everything West Virginia has to offer during the day, then retreat to Hidden Hill for the convenience of restaurants and bars at your doorstep.

Top guest favourite
The modern cabin is framed by lush greenery, showcasing a unique combination of wood and metal siding. A circular fire pit surrounded by black adirondack chairs is situated in a gravel area, leading to a pathway that connects to the entrance of the cabin.
Cottage in Lost City
4.98 out of 5 average rating, 111 reviews

Hidden Hideaway

Welcome to your retreat, your Hidden Hideaway. Leave the hustle and bustle of the city to relax and rejuvenate in Lost River. This luxury minimalist cabin has everything you want and need whether you are looking for a quick weekend getaway or a month-long working vacation. Immerse yourself in nature on the screened in porch, gaze into the Milky Way stars as you sit around the fire pit, or curl up with a book in the sun drenched reading nook, you will find what you need at Hidden Hideaway.

Top guest favourite
The cottage exterior features a combination of beige siding and stone facade, highlighting a spacious screened-in porch. A wooden deck extends from the front, offering access to the inviting outdoor space surrounded by grassy areas and shrubs.
Cottage in Shenandoah Junction
4.96 out of 5 average rating, 218 reviews

Modern, private cottage at Fairview Organic Farm

Traveling Nurses welcome. Discounts for stays of 5 nights or more. Sitting atop a hill on 23 acres at historic Fairview Organic Farm, Circa 1737, the newish cottage is surrounded by pasture, organic flower gardens, history & overlooks the Harpers Ferry Gap. We are just a few miles from Charles Town, Harpers Ferry, Shepherdstown, the Hollywood Casino, the Appalachia trail, the Shenandoah & Potomac Rivers, and many historical sites. Enjoy sun rise from the deck and sunsets from the porch.

Top guest favourite
Cottage in Bentonville
4.97 out of 5 average rating, 571 reviews

The Cottage

Need some time to refresh? Spending time in the foothills of the Skyline Drive at our cozy cottage may be for you. Well behaved dogs are welcome but not on furniture. The driveway is long and home is very secluded. Winter access will be subject to weather conditions. Driveway does not get plowed and gets rutty during rainy periods. Cell service is spotty on Browntown road. The cottage has a landline and wifi. Use your wifi calling feature for cell phone use. More info under photos.

Guest favourite
The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.
Cottage in Leesburg
4.91 out of 5 average rating, 388 reviews

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Top guest favourite
The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.
Cottage in Green Spring
4.98 out of 5 average rating, 116 reviews

The River House

A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

Top guest favourite
Two black rocking chairs are positioned on a stone patio, each adorned with a decorative pillow. A wide window provides views into the interior, framed by a white picket fence in the background, enhancing the outdoor sitting area.
Cottage in Oakland
4.96 out of 5 average rating, 192 reviews

Cheerful cottage 2 minutes from Deep Creek Lake

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

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