Winchester Vacation Rentals from $111: Search Short-Term Rentals

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

Sailor's Sunrise Cottage - Chesapeake Bay : This vacation home rental near Winchester is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winchester vacation rentals

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Port Deposit

John H.

$197 nightly

May 10 - May 11

Total with taxes and fees

Underground Railroad Barn

Kennett Square

James C.

$313 nightly

May 11 - May 12

Total with taxes and fees

Historic Chesapeake City Stay

Chesapeake City

Manjetjola P.

$263 nightly

May 10 - May 11

Total with taxes and fees

Two-story condo in luxury townhouse. Free parking.

Downtown Wilmington

Donald H.

$345 nightly

May 10 - May 11

Total with taxes and fees

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Elkton

Melissa J.

$152 nightly

May 9 - May 10

Total with taxes and fees

Country Get Away Studio Apartment

Elkton

Robert B.

$105 nightly

May 18 - May 19

Total with taxes and fees

Nature's Haven Tiny Home

Bear

James S.

$219 nightly

May 9 - May 10

Total with taxes and fees

Tiny Home Tranquil Oasis

Bear

$230 nightly

May 9 - May 10

Total with taxes and fees

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Top Winchester Hotel Reviews

Comfort Inn & Suites Newark - Wilmington

10/10 Excellent

"Above all, the room was quiet. Front desk staff was courteous and helpful. I felt that my parked car was absolutely safe. I am thankful for a great stay."

Staybridge Suites Wilmington Downtown by IHG

10/10 Excellent

"A one night stay was all we needed to see what a great hotel this is. The AGM is incredibly helpful, hotel is new, fresh and clean. Great amenities, easy parking, quiet yet right in the middle of all the activities Wilmington has to offer. A nice touch is the free breakfast and happy hour each day. I would stay here again."

Baymont by Wyndham Newark at University of Delaware

4/10 Poor

"The Good: Staff was friendly and reasonably fast The Bad: Everything else! This is the worst hotel I have ever stayed at. It is beyond run down, the carpet is disgusting, the walls needed paint years ago, the doors dont latch and this is all before I got in the room. The room itself was so run down the the door handle fell off. Nothing seemed very clean and the room had the smell of something that was kept too damp too long. To use the internet you were forced to create an account, when I finally got access in the wonky portal I learned I had to pay for premium internet if I wanted to do anything other than checking email or texting, Instagram videos never loaded and any other app that required some bandwidth didnt work either. I would never stay here again, even if they paid me. This is especially sad since I have always had good experiences at Kimpton properties, I will have to rethink visiting one again."

Best Western Plus Newark/Christiana Inn

6/10 Okay

"The hotel and room were fine however, the hot tub wasn’t working and it was not noted on the website. Also, the pool closes too early at 8 pm. We were there for a tournament and got back around 7:50, when we went to our room, the key cards did not work and when I went down to the front desk, they expected me to wait on the line of people were checking in. My daughter needed to get into the room desperately so I just went to the front of the line and said please reactivate the keys.. there was no apology given. The buffet was OK on the first day. The yogurt machine was out and no one came to add more.. and on the second day, we needed to leave early and most of the items were not put out yet even though it was past 7:30 AM ( muffins and bagels). The breakfast attendant didn’t seem to care when I asked her.. The hotel is on a main highway so ask for a room in the back. The gentleman at the front desk on Sunday morning was on his phone the entire time. Barely looked up when I left the keys. The check-in staff on Friday night was very nice. I’ll be returning."

Quality Inn Newark - Wilmington

6/10 Okay

"No one broke into my car and i didn't see any bugs. That's the best i can say for this place. I have pretty low standards, and i would not book here again. The facilities are extremely outdated. The whole place needs a few coats of paint and some elbow grease, not to mention a new elevator, some hardcore parking lot cleanup and room repairs. The staff was incredibly nice and it was surprisingly quiet but i left a night early to go check in elsewhere. "

Ramada by Wyndham Newark/Wilmington

2/10 Terrible

"I had booked to stay here however once I got to the hotel it was not what I expected so I got my money back and went somewhere else. (The staff was very nice to deal with, not her fault.) It smelt like smoke, the chair in the room was stained and disgusting, the bathroom has a cigarette burn in the shower and mold. Unacceptable. "

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 $111 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.

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Frequently asked questions

Are there vacation rentals in Winchester?

Yes, you can find vacation rentals near top local attractions in Winchester, or you can go with a secluded option if you're looking for a relaxing stay.

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

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home rental near Winchester is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

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 larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private accommodations you can stay in for several days or longer in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.

Winchester Vacation Rentals

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Check prices for these dates

Our top choices for Winchester vacation rentals

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Underground Railroad Barn

Historic Chesapeake City Stay

Two-story condo in luxury townhouse. Free parking.

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Country Get Away Studio Apartment

Nature's Haven Tiny Home

Tiny Home Tranquil Oasis

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Quarry Landing - Center of Town & River View - 3 Bedroom

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Long Beach Cottage, (romantic couple’s getaway)

Underground Railroad 4 Bedroom Farmhouse

Cozy 1-bedroom bungalow in quaint Darlington with AC

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

New Construction townhome close to everything downtown w/transparent pricing

5-bedroom vacation home 5 minutes from historic Charlestown

Homey Retreat in Historic Kennett Square!!

Entire place with private parking

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Comfort Inn & Suites Newark - Wilmington

Find out more about Winchester

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