Cottage holiday rentals in Western Maryland

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Top-rated cottage rentals in Western Maryland

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Guest favourite

Cottage in Winchester

4.98 out of 5 average rating, 306 reviews

Uber SXY 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...

14–21 Oct

$296 SGD per night

Guest favourite

Cottage in Markham

4.94 out of 5 average rating, 101 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!

18–25 Sep

$397 SGD per night

Guest favourite

Cottage in Maurertown

4.92 out of 5 average rating, 194 reviews

The Cottage at Little Ridge

The beauty of the Shenandoah Valley, the tranquility of a working family farm, and the delights of a taproom and cafe, all come together in this amazing property. This country modern one bedroom/one bath/kitchen unit is a brand new addition to Ridge Runner Farms. With its own private porch it offers views of this four acre working farm in Maurertown, VA. Ridge Runner also boasts a farm Cafe. Enjoy sunsets on your own porch or walk the 100 feet to enjoy a seat inside the welcoming cafe!

14–21 Jul

$167 SGD per night

Guest favourite

Cottage in Shepherdstown

4.96 out of 5 average rating, 109 reviews

NEW * The Getaway Cottage at Rocky Marsh Farm

Welcome to The Getaway Cottage, a charming two-bedroom, two-bath home nestled in a peaceful country setting, located just 3.5 miles from Shepherdstown. Our location offers easy access to all the exciting activities and attractions the eastern panhandle has to offer, enjoy a short country side drive to dining, shopping, hiking trails, white water rafting and kayaking adventures. The historic town of Harpers Ferry is a short 25-minute drive away, and 15 minutes to Antietam Battlefield.

17–24 Sep

$310 SGD per night

Guest favourite

Cottage in Fort Valley

4.96 out of 5 average rating, 158 reviews

Cozy Cottage/Pet Heaven

Deep breath...exhale. Looking for the perfect place to hideaway? You have found it. Enjoy big skies, picturesque landscapes, friendly farm animals and colorful sunsets. Nestled in the valley within the valley, you are surrounded by the George Washington National Forest. Offering hiking, biking, ATV trails, and so much more. Skyline Drive and Luray Caverns are just a 30 min drive. 30 minutes to shopping. Located less than 2 hours west of DC. Come see what you have been missing.

8–15 Dec

$251 SGD per night

Guest favourite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

26 Jan – 2 Feb

$171 SGD per night

Guest favourite

Cottage in Warrenton

4.97 out of 5 average rating, 264 reviews

The Soper House-A Quaint & Lovely Country Getaway

The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

17–24 Jul

$162 SGD per night

Guest favourite

Cottage in Oakland

4.98 out of 5 average rating, 100 reviews

Pet friendly-Cottage in the Woods

Tucked conveniently between Swallow Falls State Park and Deep Creek Lake, this recently renovated 2 bd cottage has everything you need for a weekend getaway or a much needed week(s) long vacation! Inside you will find a completely stocked kitchen, open living/dining area, full size bathroom, 2 bedrooms and a cozy nook with sleeper sofa and desk. Relax and unwind in the spacious backyard or charming balcony. *pets stay free

16–23 Jan

$223 SGD per night

Guest favourite

Cottage in Timberville

4.92 out of 5 average rating, 456 reviews

Cider House Orchard Stay

Welcome to the Old Hill Cider House at Showalter's Orchard! Located just steps away from the first row of Summer Rambo Apple Trees at Showalter's Orchard. The thoughtful renovation was only completed in early July. The former wash house could be a base for all your Shenandoah Valley Travels, or this light, airy and romantic little house is a comfortable and cozy place for your farm vacation.

18–25 Jan

$166 SGD per night

Guest favourite

Cottage in Shepherdstown

4.96 out of 5 average rating, 186 reviews

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!

30 Jul – 6 Aug

$160 SGD per night

Guest favourite

Cottage in Capon Bridge

4.97 out of 5 average rating, 150 reviews

The 3R's River, Relaxation, Retreat

Rustic river cabin on Cacapon River on stilts only 4 steps away from the river .Fishing ,kayaking, swimming, camp fires ,grilling and relaxing from riverside deck over looking the Cacapon River. Capon Bridge W.V is a little over a mile away with restaurants , shopping, artesian market and fresh market with local wines. Plus see the occasional American bald Eagle.

2–9 Feb

$222 SGD per night

Guest favourite

Cottage in Martinsburg

4.98 out of 5 average rating, 355 reviews

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

4–11 Nov

$153 SGD per night