Cottage vacation rentals in Western Maryland

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Top-rated cottage rentals in Western Maryland

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Guest favorite

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...

Mar 10 – 17

G$45,641 GYD per night

Guest favorite

Cottage in Markham

4.94 out of 5 average rating, 102 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!

Dec 16 – 23

G$59,704 GYD per night

Guest favorite

Cottage in Harpers Ferry

4.94 out of 5 average rating, 245 reviews

Adorable apartment with a view

This private apartment has it all. A bright, clean space with comforts of home. Great views! In addition you are centrally located to many attractions and destinations. These include the Appalachian Trail, Harpers Ferry National Park, white water rafting, Hollywood Casino, Charleston Race Track, fishing, River Riders Family Adventure, tour bus ride, shopping outlets, antique shopping, glass outlet, Skyline and Luray caverns, glass outlet, close to train station for day trips to DC, and more.

Jan 4 – 11

G$21,444 GYD per night

Guest favorite

Cottage in Winchester

4.9 out of 5 average rating, 101 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Jul 19 – 26

G$15,578 GYD per night

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 110 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.

Sep 16 – 23

G$46,637 GYD per night

Guest favorite

Cottage in Fort Valley

4.96 out of 5 average rating, 159 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.

Dec 12 – 19

G$37,640 GYD per night

Guest favorite

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.

Jul 30 – Aug 6

G$25,639 GYD per night

Guest favorite

Cottage in Spring Run

4.95 out of 5 average rating, 179 reviews

Cozy country charm

My cottage has beautiful views from every side of the house and a relaxing front porch to sit and relax and enjoy a cup of coffee. It's a cozy cottage at the foot of the mountain with lots of privacy. There are no neighbors. There are horses here to enjoy watching them graze or feed them a snack. It's truly a nice getaway and still only a half hour from 3 local towns. For warmer weather there is a firepit, picnic table, grill and some nice shaded areas to relax.

Sep 13 – 20

G$20,198 GYD per night

Guest favorite

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.

Aug 13 – 20

G$24,276 GYD per night

Guest favorite

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.

Nov 13 – 20

G$24,989 GYD per night

Guest favorite

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!

Oct 2 – 9

G$25,125 GYD per night

Guest favorite

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.

Feb 8 – 15

G$33,381 GYD per night