Winchester Holiday Rentals from €121: Search Short-Term Rentals

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Holiday Rentals in Winchester

Stylish entrance with wooden steps and glass door, set amidst a modern architectural design.

"Very clean.. Great location! "

includes taxes & fees

12 Aug - 13 Aug

Relax in this charming attic room with a sloped ceiling, central window, and cozy wooden elements.

"Everything was as described. We had a lovely weekend relaxing under the stars in the hot tub and spending time with family in the Shenandoah Valley. We can't wait to come back to this oasis!"

includes taxes & fees

28 Jul - 29 Jul

Relax in a serene outdoor space surrounded by lush greenery and a stone wall.

"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"

includes taxes & fees

15 Jul - 16 Jul

Enjoy a meal or a moment of peace on the deck, surrounded by lush greenery and a tranquil atmosphere.

"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."

includes taxes & fees

15 Jul - 16 Jul

includes taxes & fees

28 Jul - 29 Jul

Enjoy cooking in this well-equipped kitchen with an oven, coffee maker, and dining area.

"Property is freshly renovated, very clean, nicely appointed. There was a pervasive musty/mildewy smell throughout the unit, i expect there is a leak somewhere from the renovation. Also, while well appointed, there were no hospitality items...usually there is at least coffee/tea, especially at this price point. We enjoyed our stay and the location was convenient to the theater and the downtown area."

Kitchen features oven, microwave, and toaster, with a window and hanging plant.

"We needed a place to stay for our golf foursome. Thisfour bedroom property met all of our needs."

includes taxes & fees

15 Jul - 16 Jul

Enjoy the serene surroundings from the open deck, featuring a fire pit and stunning views.

"Great stay and very accommodating for outings/get together with friends. We loved the fire pit area. Great views of the Shenandoah river as well."

includes taxes & fees

30 Jul - 31 Jul

Relax in a serene outdoor space with a pergola, sofa, and comfortable seating.

"Really enjoyed our stay. The house was lovely with amazing views. The bar and game room were fun. Lots of detail and thought were put into making this house feel like home. We will definitely be back!"

includes taxes & fees

21 Jul - 22 Jul

Kitchen features a refrigerator, microwave, coffee maker, and sink with a faucet.

"The house was clean, the kitchen had sufficient utensils and supplies, the location was close to restaurants."

includes taxes & fees

22 Jul - 23 Jul

Enjoy cooking in this well-equipped kitchen with an oven, microwave, and dishwasher.

"View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. "

includes taxes & fees

12 Aug - 13 Aug

Relax in a hot tub surrounded by a lush landscape and water views, with comfortable outdoor seating and a modern design.

"The place is amazing and the host was quick with the response! Me and my family had a great time and will be returning guests!!!"

includes taxes & fees

15 Jul - 16 Jul

Enjoy meals in this kitchen with stainless steel appliances and a dining area with a wooden table.

"The apartment is great. I suspect it would be particularly awesome for a long-term stay. It's a basement apartment, so stairs weren't a surprise. Obviously, if you're not mobile, you won't pick this apartment. However, if you're a little wobbly, the stairs only have one handrail (it's not sketchy, but I rely pretty heavily on my handrails, and this one was not comforting), the bathroom floor is shiny and terrifying, the walk to the unit is bumpy, with lots of tree roots, uphill, and possibly...

includes taxes & fees

29 Jul - 30 Jul

Relax by the fire pit in a serene outdoor space surrounded by Adirondack chairs and string lights.

"Cute little house perfect for a small town getaway. The house was a perfect fit for my family of 5. We were able to walk to the shops and enjoyed a nice day of shopping. We will be back!"

includes taxes & fees

13 Aug - 14 Aug

Enjoy cooking in this well-equipped kitchen with a central island and stools.

"This was an amazing property for (my now) wife, bridal party & myself. All rooms had their own bathroom & the common area on the top floor was good for isolating any noise!"

includes taxes & fees

10 Aug - 11 Aug

Enjoy cooking in this well-equipped kitchen with a microwave, oven, and stove.

"Location was great! We enjoyed our stay in this old historical home that has been completely updated. Property manager was super communicative and easy to work with. 10 out of 10 would stay here again. "

includes taxes & fees

28 Jul - 29 Jul

Enjoy cooking in this well-equipped kitchen with a large island, central sink, and ample lighting.

"Would highly recommend this property for a stay in Leesburg. Great walkable locations to coffee, shops and restaurants. The house was just what we needed and made for a wonderful weekend away."

Relax in this inviting outdoor seating area with sofas, armchairs, and a central table featuring a fire feature.

"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "

includes taxes & fees

15 Jul - 16 Jul

Kids can play on the playground's slides and climbing elements.

"The townhouse was great- very clean and plenty of room for my family of six. I do wish there was a bigger bed in the Master bedroom- the mattress was thin and the bed was squeaky to sleep in. Property manager was great- very easy to communicate with very helpful. "

includes taxes & fees

28 Jul - 29 Jul

Relax in style with a hot tub and lounge chairs on the deck, surrounded by lush greenery and twinkling lights.

"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "

includes taxes & fees

15 Jul - 16 Jul

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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, apart-hotels, 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 €121 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.

Recent reviews of Winchester properties

Fairfield Inn & Suites by Marriott Winchester

5/5 Excellent

"Unbelievably friendly and helpful staff. The woman works the breakfast is so kind and overly accommodating! Highly recommend."

A verified traveller stayed at Fairfield Inn & Suites by Marriott Winchester

Posted 1 day ago

SpringHill Suites by Marriott Winchester

5/5 Excellent

"The location is ideal for road warriors, with a large selection of restaurants and stores either walking distance or a short drive away. The room was spacious, and the couch's trundle bed was a nice touch as opposed to awkward fold-out sofa beds. We were also happy for the late checkout on Saturday, with a hearty breakfast offered until 11am. What a nice touch! If we are ever passing through the area, we are certain to stay here again."

A verified traveller stayed at SpringHill Suites by Marriott Winchester

Posted 3 days ago

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All accommodation types in Winchester

Villas in Winchester

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?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This holiday home rental outside of Winchester is located on a river, 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 19 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market 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 Jim Barnett Park.

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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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Juliana Spa Suite - Luxury Main Floor

Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

Historic Bluemont Village Home

Newly renovated Farm cottage with Mountain views

Welcome to the Ladybug Retreat!

Cameron Charmer pristine downtown apt with double master suites

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

Windy Knoll Adventure!

Sunset Haven - 10 min from Skyline Drive. Hot Tub

Big Sunny Family House

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Pirate's Cove River Front Oasis, Group Adventure

Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

The Cottage on Royal - Historic Leesburg Home

'Thomson Farm' Classic Home < 10 Mi to Vineyards!

Quaint Royal Cottage @ Historic Leesburg

Retreat in Historic Downtown Leesburg - Walkable to Everything!

Cottage on King | Charming Historic Leesburg Home

Balcony & Pool Access: Modern Gainesville Home

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

Find out more about Winchester

Recent reviews of Winchester properties

Fairfield Inn & Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester

Microtel Inn & Suites by Wyndham Winchester

Sleep Inn & Suites

Hampton Inn Winchester N/Conference Center, VA

SpringHill Suites by Marriott Winchester

La Quinta Inn & Suites by Wyndham Winchester

Comfort Inn & Suites

Country Inn & Suites by Radisson, Winchester, VA

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Frequently asked questions