Winchester Holiday Rentals from €383: Search Short-Term Rentals

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

Homey Retreat in Historic Kennett Square!! : This holiday home rental outside of Winchester offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

Check Winchester holiday rental availability

Holiday Rentals in Winchester

"We were relaxing and visiting Mt. Cuba. Wanted to stay in-town. House was adorable and location was great. Lots of nice touches to make everything comfortable (tea, extra blankets, multiple keys). Would absolutely come back!"

includes taxes & fees

29 Nov - 30 Nov

"Cute and cozy home, Host is a great communicator. "

"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"

On the beach, sun-loungers, beach towels

"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."

"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."

"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."

"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."

includes taxes & fees

3 Dec - 4 Dec

"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."

"Loved the preserved historic quality of the property. So tastefully furnished and lovely. Nice and quiet neighborhood. The exposed beams certainly let you know when someone was in the room over your head but so worth it for the character."

"Property was clean and close to everything in Chesapeake City"

includes taxes & fees

30 Nov - 1 Dec

"Cozy and comfortable. Barnyard animals so close at hand it offered a taste of country life, including the rooster wake-up call."

"Our trip to the Lancaster area wouldnt have been as great without this amazing place to stay. Our host was great and the property was beautiful. Lots of time and places to take a deep breath and relax. We went to Sight and Sound which wasnt far from the farm and also went to a concert in Baltimore one night just over an hour away. It was great to meet our new farm friends and give them treats (ask permission). If you are looking for a home base in the Lancaster area, this is it. Kids would...

"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."

"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...

"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"

"The house was perfect for our stay. We were in town for a family event and needed a place for 8 adults and 4 children and this was perfect. Lots of space to spread out with a great rec room that kept both kids and adults entertained during down time. The neighborhood was beautiful and had easy access to area restaurants and shopping. Close to many area attractions. It was the perfect location to have close proximity to points of interest and then return to at end of day to a relaxing...

"Great value, was a great jumping point for our group, who was here for a wedding"

"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"

"Place was great !"

"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"

includes taxes & fees

3 Dec - 4 Dec

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Other types of properties in Winchester you may be interested in

"Great people "

includes taxes & fees

28 Nov - 29 Nov

"Ask for a room on the front of the hotel. There's a lot of traffic noise on the back side"

includes taxes & fees

15 Dec - 16 Dec

"Top notch accommodations, well appointed , very friendly & I appreciate the flexibility of daily room service or not. "

includes taxes & fees

20 Dec - 21 Dec

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 €383 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 Wilmington New Castle

5/5 Excellent

"Parking is $24.99, not acceptable for the cost you pay for a night "

A verified traveller stayed at Fairfield Inn & Suites Wilmington New Castle

Posted 12 hours ago

Comfort Inn & Suites Newark - Wilmington

5/5 Excellent

"I especially liked the complementary breakfast which offered many choices. I liked that you could get coffee anytime. And fresh lemon infused water was available in the lobby. I also appreciated having a microwave, refrigerator and coffeemaker in my room. Extra pillows on the very comfortable bed were a plus, as was the controllable A/C thermostat. The effective blackout curtains & the quiet were wonderful! All in all, a very favorable experience."

A verified traveller stayed at Comfort Inn & Suites Newark - Wilmington

Posted 7 days ago

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

Homey Retreat in Historic Kennett Square!!: This holiday home rental outside of Winchester offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Fred Rust Ice Arena, or get outside and enjoy nature at Fair Hill State Natural Resources Management Area. University of Delaware and University of Delaware Botanic Gardens are a couple of places you'll find in the wider area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you to 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 popular choice for a small group gathering.

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Holiday Rentals in Winchester

Check Winchester holiday rental availability

Holiday Rentals in Winchester

Homey Retreat in Historic Kennett Square!!

Historic Kennett Square

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterfront house with amazing views. Top of the Chesapeake

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Historic home in the heart of Main Street- walkable to shops and restaurants

Stunning waterfront villa with indoor pool and kids swing set and play area.

Beautiful Colonial Style Home in Nottingham PA

Historic Chesapeake City Stay

Cozy loft tucked away on the beautiful Chester and Lancaster County line.

Lancaster co. farmhouse in the heart of amish country

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!

Chesapeake City Quiet Overlook

Welcome to Woodview Estates!

Wilmington Comfort 4 Min to Riverfront fenced yard

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Private Carriage House Retreat on a 33 Acre Historic Working Estate

Top of the Chesapeake - Minutes from Historic Charlestown

Other types of properties in Winchester you may be interested in

Sonesta Select Newark Christiana Mall

Fairfield Inn by Marriott Kennett Square Brandywine Valley

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Find out more about Winchester

Recent reviews of Winchester properties

Fairfield Inn & Suites Wilmington New Castle

Staybridge Suites Wilmington Downtown, an IHG Hotel

Days Inn by Wyndham Newark Wilmington

Sheraton Suites Wilmington Downtown

Quality Inn

Hyatt Place Wilmington Riverfront

Ramada by Wyndham Newark/Wilmington

Sonesta Select Newark Christiana Mall

Comfort Inn & Suites Newark - Wilmington

Frequently asked questions