A white neoclassical building with columns, an American flag, and a clock tower.

Winchester Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Winchester vacation rentals

A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

1. Executive Suites

Winchester

$212 nightly

Dec 12 - Dec 13

Total with taxes and fees

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

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

Winchester Historic District

Timothy B.

$219 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

3. Rosamond nice downtown studio apt

Winchester Historic District

Jameson D.

$162 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

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

Winchester

Chris C.

$227 nightly

Nov 30 - Dec 1

Total with taxes and fees

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

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

Winchester Historic District

Leslie L.

$190 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

6. Morocco Loft 2BR overlooking city walking mall

Old Town Winchester

Kristen R.

$253 nightly

Nov 12 - Nov 13

Total with taxes and fees

A two-story house with a front porch, a mailbox, and a number plate.

7. Cameron Charmer pristine downtown apt with double master suites

Winchester

Carolyn F.

$294 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Stephens City

Laura H.

$157 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

9. The Stock Exchange downtown 3rd floor studio apt

Winchester Historic District

Greg A.

$167 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden deck with white railings and a covered porch area.

10. Mountain View Bungalow in Front Royal

Front Royal

Onon

$184 nightly

Nov 22 - Nov 23

Total with taxes and fees

A living room with a sofa, armchair, coffee table, and a television.

11. Nostalgia Lane in the heart of the city

Old Town Winchester

Melissa J.

$270 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern, dark-colored triangular building with a balcony and outdoor seating area.

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

Stephens City

Laura V.

$348 nightly

Nov 30 - Dec 1

Total with taxes and fees

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

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

Front Royal

Denise A.

$349 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cozy living room with a grey sofa, patterned cushions, a small side table with a lamp, and decorative vases.

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

Front Royal

Jake M.

$193 nightly

Nov 12 - Nov 13

Total with taxes and fees

A garden with a wooden swing set and a circular seating area.

15. Newly renovated Farm cottage with Mountain views

Strasburg

Marsha N.

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

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

Strasburg

Paul S.

$436 nightly

Nov 12 - Nov 13

Total with taxes and fees

A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

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

Front Royal

P H.

$336 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

18. Blue Mountain Cabin, secluded, perfect for couples, near main road

Front Royal

Carla M.

$221 nightly

Nov 12 - Nov 13

Total with taxes and fees

A two-story house with a balcony, surrounded by trees and snow.

19. Cozy A frame cabin in quaint Front Royal. Dog friendly

Front Royal

Kye Y.

$243 nightly

Nov 12 - Nov 13

Total with taxes and fees

An outdoor dining area with a wooden deck, a table set for four, and a view of the surrounding greenery.

20. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

Front Royal

$273 nightly

Nov 17 - Nov 18

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

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

Glen Gordon Manor

Huntly

10/10 Excellent

Omar

A two-story house with a front porch, American flags, and a mailbox.

The Carriage Inn B&B

Charles Town

10/10 Excellent

retired teacher

An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

TownePlace Suites by Marriott Front Royal

Front Royal

10/10 Excellent

JoEllen

An outdoor patio area with wicker furniture, a stone fire feature, and a covered seating area with string lights.

Home2 Suites by Hilton Charles Town

Charles Town

10/10 Excellent

Tommy

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

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

Knoxville

10/10 Excellent

Johnna

A modern house with a stone facade, large windows, and a sloped roof.

Goodstone Inn & Restaurant

Middleburg

10/10 Excellent

Adrian

A gazebo with a brick pathway leading to it, surrounded by a grassy area with purple flowers.

Loudoun Valley Manor

Waterford

10/10 Excellent

My partner and I stayed here for two nights, and had a relaxing little vacation away from the bustle of D.C. Olga was a lovely host and made us feel very welcome. She cooked omelettes bright and early every morning, and always had coffee, tea, and snacks available throughout the day. There are a lot of vineyards and breweries nearby to visit, and the air-conditioned rooms were a comfortable retreat from the afternoon heat. The house was pristine, gorgeously decorated, and the view of the...

Anonymous traveler

A modern hotel lobby with a central seating area, a reception desk, and a bookshelf filled with books.

Hilton Garden Inn Haymarket

Haymarket

10/10 Excellent

Anonymous traveler

A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

Quality Inn Winchester

Winchester

10/10 Excellent

Paul

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

10/10 Excellent

Kelley Ann

An outdoor patio with a fire feature, seating, and a covered area.

SpringHill Suites by Marriott Winchester

Winchester

10/10 Excellent

Lynette

A covered porch with white columns, a bench, and hanging flower baskets.

L'Auberge Provencale Inn & Restaurant

Boyce

10/10 Excellent

Mary

A building with classical architecture, featuring columns and a symmetrical facade.

Hampton Inn & Suites Charles Town

Charles Town

10/10 Excellent

Trisha

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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Things to do in Winchester
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