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Winchester Vacation Rentals

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

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    Our top choices for Winchester vacation rentals

    1. Executive Suites

    A modern apartment with a spiral staircase, a living area with a dark-colored sofa, a coffee table, and a kitchen in the background.

    2. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

    A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

    3. Morocco Loft 2BR overlooking city walking mall

    A living room with a sofa, ottoman, lamp, and a mirror.

    4. Rosamond nice downtown studio apt

    A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

    5. The Queen of Winchester Three Bedroom with Upper Level Deck

    A covered deck with outdoor furniture and a grill.

    6. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

    A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

    7. Cameron Charmer pristine downtown apt with double master suites

    A backyard patio with a stone-tiled floor, a wooden table with chairs, a barbecue grill, and a wooden fence.

    8. Luxury tiny home farm stay on historic property with hot tub in Stephens City

    A hot tub in front of a wooden cabin with a tree in the background.

    9. Nostalgia Lane in the heart of the city

    A living room with a sofa, coffee table, and lamps. There is a bookshelf and a framed picture on the wall.

    10. Chalet w/Hot Tub, Deck, Game Room & EV Charger

    A modern house with a large window, a covered porch, and outdoor seating.

    11. The Stock Exchange downtown 3rd floor studio apt

    A building with a red door, white trim, and a small balcony with a metal railing.

    12. Mountain View Bungalow in Front Royal

    A wooden deck with a ceiling fan, white door, and windows.

    13. The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6

    A house with a fire pit in the foreground and a deck with string lights in the background.

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

    A hot tub area with a wooden structure overhead, a bottle, and glasses.

    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. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

    A cozy outdoor seating area with a sofa and a fire pit, wooden deck, and a glass door leading to an interior space.

    17. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

    A hot tub on a deck with a white railing and greenery in the background.

    18. Mountaintop Cottage | Private Hot Tub

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

    19. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

    A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

    20. Mountain View Cottage | Hot Tub & Game Room

    A two-story house with a balcony, a deck, and a stone retaining wall.

    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.

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    Find vacation rentals that suit your style

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    Top Winchester Hotel Reviews

    Glen Gordon Manor

    A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

    The Carriage Inn B&B

    A garden with a statue, flowering shrubs, and a brick pathway.

    Home2 Suites by Hilton Martinsburg, WV

    An outdoor seating area with a stone fire pit, cushioned benches, and string lights.

    Home2 Suites by Hilton Charles Town

    A hotel with a prominent "HOME" sign, outdoor seating area, and a covered entrance.

    Holiday Inn Express & Suites Brunswick - Harpers Ferry Area by IHG

    A Holiday Inn Express hotel with a modern design, featuring a stone facade, multiple windows, and a covered entrance.

    Hotel Burg

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

    Goodstone Inn & Restaurant

    A four-poster bed with a white bedspread, two bedside tables with lamps, a chair with a tray of food, and a window with a view of greenery.

    Loudoun Valley Manor

    A gazebo with a paved pathway leading to it, surrounded by greenery and a sunset in the background.

    Hilton Garden Inn Haymarket

    A modern dining area with round tables and wicker chairs, large windows, and a wooden ceiling.

    The George Washington Hotel, A Wyndham Grand Hotel

    An outdoor patio with brick walls, tables, chairs, and string lights.

    SpringHill Suites by Marriott Winchester

    An outdoor patio with a fire feature, seating, and a covered area with a view of the building's interior.

    Hampton Inn & Suites Charles Town

    A spacious hotel lobby with multiple seating areas, a long communal table, and large windows offering views.

    L'Auberge Provencale Inn & Restaurant

    A bar area with wooden shelves stocked with bottles, a bar counter, and leather bar stools.

    Light Horse Inn

    A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.

    Find out more about Winchester

    Everything you need to know about Winchester vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Winchester vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $174 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Winchester rentals

    At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find vacation rentals in Winchester?

    Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

    What are some of the best vacation home rentals in Winchester?

    Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home near Winchester is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

    How many vacation rentals will I find in Winchester?

    Choose from 15 Expedia vacation rentals in Winchester for a memorable vacation.

    What’s there to see and do in Winchester?

    Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of family-friendly sights, whereas cultural attractions include Bright Box Theater and Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Apple Blossom Mall.

    What’s a vacation rental in Winchester like?

    A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.

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