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...

Oct 8 – 15

R3,986 ZAR per night

Guest favorite

Cottage in Maurertown

4.92 out of 5 average rating, 193 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!

Jun 2 – 9

R2,255 ZAR per night

Guest favorite

Cottage in Fort Valley

4.96 out of 5 average rating, 157 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 13 – 20

R3,465 ZAR per night

Guest favorite

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.

Jul 8 – 15

R4,239 ZAR per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 424 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.

Feb 4 – 11

R2,309 ZAR per night

Guest favorite

Cottage in Spring Run

4.95 out of 5 average rating, 178 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.

Jun 4 – 11

R1,889 ZAR per night

Guest favorite

Cottage in Lovettsville

4.97 out of 5 average rating, 195 reviews

Cottage Escape in Virginia Wine Country

Nestled along the Blue Ridge Mountains, LoeLynn Farms is the quiet escape you need. The two story cottage offers two car parking next to the front door, a fully equipped kitchen, outdoor living, lake access and most importantly- peace and relaxation. The Cottage is conveniently located to many wineries, breweries, exceptional restaurants and outdoor adventures. We are just 90 minutes outside of Washington, D.C. in the heart of Loudoun County Wine Country.

Dec 14 – 21

R3,357 ZAR per night

Guest favorite

Cottage in Timberville

4.92 out of 5 average rating, 454 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.

Dec 31 – Jan 7

R2,245 ZAR per night

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 183 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!

Apr 3 – 10

R2,276 ZAR per night

Guest favorite

Cottage in Arbovale

4.94 out of 5 average rating, 186 reviews

Historical 1800s Cottage

Historical cozy cottage built in the mid 1800s conveniently located near the Green Bank Observatory, Snowshoe Mountain Resort, the National Forest and loads of hiking and biking trails. From the back yard, you can access hiking trails which connect to the Observatory's many hiking and biking trails. Cass Scenic Railroad and the Greenbrier River are only 6 miles away.

Oct 9 – 16

R1,499 ZAR per night

Guest favorite

Cottage in Capon Bridge

4.97 out of 5 average rating, 149 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.

Oct 13 – 20

R3,006 ZAR per night

Guest favorite

Cottage in Morgantown

5.0 out of 5 average rating, 265 reviews

Copper House

Copper House is a light, airy, tree-shaded lakefront home. Situated in a private community on a 20 acre lake, this home is a short 15 minute drive to downtown Morgantown and 10 minutes to the I-79 / US-68 interchange. A large 12'x35' deck overlooks the lake in the rear. Ideal area for relaxing or grilling. Please note: we do not allow large parties.

Feb 22 – Mar 1

R3,306 ZAR per night