Cottage vacation rentals in Jefferson County

Historic Stone Schoolhouse on Winery Row

This antique schoolhouse building has been repurposed and has every modern convenience. It has been newly furnished and outfitted for relaxation and enjoyment of the scenic and historic area. Offers an expansive pergola deck with outdoor dining and lounge seating as well as a gas grill. The 3-acre lot provides space for playing yard games and offers a super firepit by a bold stream at the back of the property. Many wineries, breweries, historic sites, and outdoor recreation are very close by.

C&O Canal/Potomac River Lock Keepers Cottage

Located just steps away from Dam #4 on the C&O Canal / Potomac River. (marker 84.6) Perfect for a getaway or romantic weekend. Hike/bike the C&O Canal, bring your kayak/canoe/bikes, fish or swim in the river. Sit on the porch and listen to the rumble of the water falling over the dam. Local lore is this was the home of a canal lock keeper or the gate house keeper. Secluded location away from town. NOT A PARTY HOUSE/owner on site in garage apartment. Inquire if a blocked day is available.

Riverfront Cottage in Shepherdstown, WV

Escape to this tranquil, riverfront retreat with stunning, year-round river views, a private dock (available late May-Sept) & firepit. Relax, fish, explore, or visit nearby attractions in Shepherdstown, Sharpsburg, & Harper's Ferry. Two kayaks, a canoe, paddles, & lifejackets are available for your use. All water activities are at your own risk. WV DNR requires all boaters to have a lifejacket and all boats to have a whistle. Please bring your own whistle(s). MD or WV fishing license is fine.

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.

A little piece of the country in the town

Located in the scenic town of Harpers Ferry, this sunny little cottage is tucked away in a great little neighborhood full of friendly people and backyard chickens. The neighborhood has restaurants, a wonderful bakery, two local bars, and we are a 20 minute walk from historic Harpers Ferry. The cottage is owned by two local old time Appalachian musicians, so you might hear some fiddle tunes drifting through the air if you are deck sitting. Bedroom has a queen bed No cleaning fees

Modern, private cottage at Fairview Organic Farm

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 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.

Wild & Cozy | Harpers Ferry Mountain Escape

Enjoy a charming, rustic getaway in our mountain cottage by Lake Shannondale! This 4bd/2ba pet-friendly home with a 6-person jacuzzi, king-sized beds, pool table, is perfect for families and large groups! ★ "the Airbnb was better than the pictures." ★ "wish we could have stayed longer!" You are only: ☞ 5 minutes from The Appalachian Trail ☞ 20 minutes from Harpers Ferry ☞ <20 minutes from 20+ wineries & breweries

The Creekside Cottage: Downtown | Pet-Friendly

Welcome to the Creekside Cottage, a 2 bedroom/1.5 bathroom spacious home, offering a secluded escape by the creek yet just a short stroll through the gardens of Shepherdstown to shopping and dining. Perfect for getaways, family visits, or university stays, this Creekside Cottage offers a roomy interior, cozy living room, modern kitchen, fire pit, and a private patio & porch to be enjoyed along the Town Run.

Family & Pet Friendly- Hot Tub-Full Kitchen

Book our contemporary residence in Harpers Ferry, WV if you're into outdoor activities like hiking, kayaking, and fishing. Our home is close to natural attractions, including the Shenandoah river, Appalachian Trail, and WMA. Also nearby are the Harpers Ferry Adventure Park and Charles Town Casino. Local breweries, wineries, and dining options are available to satisfy your taste buds.