Winchester Holiday Rentals from NZ$312: Search Short-Term Rentals

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Our top choices for Winchester holiday 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

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

19 Nov - 20 Nov

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.

includes taxes & fees

12 Nov - 13 Nov

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.

includes taxes & fees

16 Nov - 17 Nov

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.

includes taxes & fees

19 Nov - 20 Nov

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

6. Morocco Loft 2BR overlooking city walking mall

Old Town Winchester

Kristen R.

includes taxes & fees

15 Nov - 16 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

17 Nov - 18 Nov

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.

includes taxes & fees

12 Nov - 13 Nov

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

10. Mountain View Bungalow in Front Royal

Front Royal

Diedra

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

7 Dec - 8 Dec

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.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

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

15. Newly renovated Farm cottage with Mountain views

Strasburg

Marsha N.

includes taxes & fees

30 Nov - 1 Dec

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

16 Nov - 17 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

11 Nov - 12 Nov

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

includes taxes & fees

16 Nov - 17 Nov

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Find holiday rentals that suit your style

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as NZ$312 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

What are some of the best holiday rentals that Winchester has to offer?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a balcony and a BBQ 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 holiday with amenities such as a selection of games.

How many holiday rentals will I find in Winchester?

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

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the 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 holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.

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Winchester Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester holiday rentals

1. Executive Suites

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

3. Rosamond nice downtown studio apt

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

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

6. Morocco Loft 2BR overlooking city walking mall

7. Cameron Charmer pristine downtown apt with double master suites

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

9. The Stock Exchange downtown 3rd floor studio apt

10. Mountain View Bungalow in Front Royal

11. Nostalgia Lane in the heart of the city

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

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

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

15. Newly renovated Farm cottage with Mountain views

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

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

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

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

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

Find holiday rentals that suit your style

Find out more about Winchester

Winchester holiday rentals: An excellent choice for every season

How to find incredible deals on Winchester rentals

Frequently Asked Questions

Can I find holiday rentals in Winchester?

What are some of the best holiday rentals that Winchester has to offer?

How many holiday rentals will I find in Winchester?

What’s there to see and do in Winchester?

What’s a holiday rental in Winchester like?

Explore a world of travel with Expedia