Plan your trip

A rural landscape with rolling hills, a variety of trees, and a cloudy sky.

Search Berryville Cottage Rentals from CA $142

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Sign in

  • Be picky

    Search almost a million properties worldwide

  • Find vacation rentals that suit your style

    Cabins

    Apartments

    Cottages

    Chalets

    Villas

    Condos

    Check prices for these dates

    Check prices for these dates, December 14–15, 2026

    View in a map

    Our top choices for Berryville cottages

    1. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

    A hot tub under a wooden pergola with a grassy yard and trees in the background.

    2. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

    A covered deck with a table and chairs, overlooking a river and autumn foliage.

    3. Peaceful Lakefront Cottage with Mountain Views!

    A hot tub on a deck with a view of a lake and forest.

    4. Woodsy Retreat with a Hot Tub and Seasonal Views!

    A modern building with large windows, a deck, and a stone wall.

    5. Cottage w/ Hot Tub and 100-Mile Valley Views!

    A hot tub with a view of a forested landscape during sunset.

    6. Mountain View Cottage with Hot Tub and River Views

    A covered outdoor area with a fire pit, seating, and a view of the landscape.

    7. Quaint Mini Cottage in Shepherdstown - Walking Distance

    A living room with a dining table, chairs, a sofa, and a television.

    8. The Carriage House at Carrot Top Cottage

    A bedroom with a bed, a table, and a view of the outdoors.

    9. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

    A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

    10. Mountain View Cottage | Hot Tub & Game Room

    A hot tub on an outdoor deck with a view of trees and hills.

    11. Mountaintop Cottage | Private Hot Tub

    A covered outdoor area with a fire pit, seating, and a view of the landscape.

    12. 18th Century Stone Cottage minutes from historic Middleburg

    A stone house with a chimney, surrounded by a well-maintained lawn and trees.

    13. Walk to Stores: Home in Historic Shepherdstown!

    A two-story house with a front lawn and trees in the background.

    14. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

    A two-story house with a covered porch and a wooden fence.

    15. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

    A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

    16. The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

    A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

    17. Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV

    A two-story house with a porch, a front door, and a number '190' sign.

    18. Renovated 3B/3B Home | Downtown | Private Fire Pit

    A two-story house with a porch and a front door.

    19. Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia

    A historic building with a brick facade, multiple windows, and a covered porch area.

    20. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

    A stone house with a white picket fence, a front porch, and potted plants.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

    View all properties

    Learn more about Berryville

    Stroll down charming Main Street to discover local artisan shops and the historic Barns of Rose Hill cultural centre. Nearby Shenandoah National Park offers scenic hiking trails, while Clarke County's wineries invite visitors to savour Virginia's finest vintages.

    See all hotels in Berryville

    A rural landscape with rolling hills, a variety of trees, and a cloudy sky.

    Top reviews in Berryville

    La Quinta Inn & Suites by Wyndham Winchester

    A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

    Hampton Inn Winchester N/Conference Center, VA

    A Hampton Inn hotel with a modern facade, multiple windows, and a welcoming entrance.

    Microtel Inn & Suites by Wyndham Winchester

    A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

    Quality Inn Winchester

    A hotel with a covered outdoor area, a parking lot, and well-maintained landscaping.

    Fairfield Inn & Suites by Marriott Winchester

    A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

    TownePlace Suites by Marriott Winchester

    A multi-story hotel with a sign reading "Towneplace Suites by Marriott."

    Spark by Hilton Winchester

    A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

    The George Washington Hotel, A Wyndham Grand Hotel

    A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

    Comfort Inn & Suites Winchester

    A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

    Home2 Suites by Hilton Charles Town

    An outdoor patio area with wicker furniture, a fire pit, and a view of the parking lot.

    Hampton Inn Winchester-University/Mall Area

    A Hampton Inn by Hilton hotel with a clear sky and sunset.

    Hilton Garden Inn Winchester

    A multi-story hotel with a prominent entrance, outdoor seating area, and a parking lot.

    Frequently Asked Questions

    Why book your cottage in Berryville with Expedia?

    Booking a cottage in Berryville is as easy as working out your travel dates and selecting an ideal place for a vacation in the outdoors. From upmarket retreats to budget-friendly properties and cottages that come with amenities like a kitchenette, Expedia has something for all traveler tastes. As for the best offers around? We've got them as well!

    How can I find cheap cottages in Berryville?

    Expedia is here to help you track down cheap cottages in Berryville. To discover a fantastic stay in just a few keystrokes, simply use our convenient filter tool to refine your search by amenities, budget and star rating.

    What is there to do in Berryville near my cottage?

    You'll find loads of fabulous things to fill your days in Berryville. Make tracks to attractions like The Fire House Gallery, Barns of Rose Hill and Watermelon Park Campground. Mackintosh Fruit Farm, Holy Cross Abbey and 612 Vineyard also lure many visitors.

    Explore a world of travel with Expedia