Winchester Holiday Rentals

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Holiday Rentals in Winchester

Thunder Hill Retreat - Spacious/Deck/Hot tub

Lincoln University
10.0 out of 10, Exceptional, (16)
"Great property, space and location for the boys and dad to have there own space, big elk creek for fishing and grill was fabulous to do chicken and burgers for a large group"
United States
Richard F.
The price is AU$737
includes taxes & fees
17 Nov - 18 Nov
Thunder Hill Retreat - Spacious/Deck/Hot tub

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

Port Deposit
10.0 out of 10, Exceptional, (11)
"Amy has a beautiful home, filled with character and special touches. We absolutely loved our stay and have zero complaints. The location was wonderful and we were extremely comfortable."
United States
Geoff F.
The price is AU$330
includes taxes & fees
16 Nov - 17 Nov
Quarry Landing - Center of Town & River View - 3 Bedroom

Underground Railroad 4 Bedroom Farmhouse

Kennett Square
9.8 out of 10, Exceptional, (22)
"Clean and exactly as listed. Perfect for families. Beautiful house, beautiful property, beautiful area. Highly recommend. "
United States
Yvonne L.
The price is AU$444
includes taxes & fees
17 Nov - 18 Nov
Underground Railroad 4 Bedroom Farmhouse

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (18)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
The price is AU$432
includes taxes & fees
17 Nov - 18 Nov
Historic Chesapeake City Stay

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

2.0 star property
Elkton
9.8 out of 10, Exceptional, (6)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$250
includes taxes & fees
15 Nov - 16 Nov
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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

Port Deposit
10.0 out of 10, Exceptional, (30)
"This was our second time staying at this site. Always very clean, quiet and enjoyable."
United States
Chris S.
The price is AU$326
includes taxes & fees
16 Nov - 17 Nov
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Underground Railroad Barn

Kennett Square
9.8 out of 10, Exceptional, (26)
"Great property. Good for dogs, full fenced in yard. "
United States
David R.
The price is AU$444
includes taxes & fees
17 Nov - 18 Nov
Underground Railroad Barn

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

2.0 star property
Nottingham
9.6 out of 10, Exceptional, (10)
"It's a rustic but very cozy place. It was very clean and was stocked with so many niceties. Very classy and just lovely. The stairs are kind of steep so you might want to take that into consideration. We walked up to the barn area and met some of the animals - the turkeys and donkeys are quite sociable and very cute! The surrounding area is bucolic. All in all, a really nice place to get away from it all."
United States
LISA L.
The price is AU$361
includes taxes & fees
17 Nov - 18 Nov
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens

Kennett Square
10.0 out of 10, Exceptional, (35)
"Everything was thought of and our host was so responsive and helpful. Loved our stay, we’ll be back! "
United States
Anya M.
The price is AU$514
includes taxes & fees
17 Nov - 18 Nov
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

2.0 star property
Wilmington
8.0 out of 10, Very good, (3)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is AU$561
includes taxes & fees
16 Nov - 17 Nov
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"Cozy and very suitable. No issues, quiet and clean. "
United States
Rich D.
The price is AU$519
includes taxes & fees
16 Nov - 17 Nov
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Welcome to the Mushroom Capital of the World!

Kennett Square
10.0 out of 10, Exceptional, (11)
"I love how artistic and unique this lodging is! Owner is a mixed media artist and her unique artwork and eye are represented throughout the space. It was clean and very comfortable. Many extra amenities were in the space. I always enjoy a king size bed and it was very comfortable. Our extra guest slept well on the couch made into a bed easily. We had one issue, I've never encountered before with this type of lodging - we did not receive any check in information and the host was not...
United States
Julie H.
The price is AU$234
includes taxes & fees
19 Nov - 20 Nov
Welcome to the Mushroom Capital of the World!

Cozy loft above ink shop

Bear
9.4 out of 10, Exceptional, (3)
"Host was extremely responsive, place was in a great location for the lacrosse tournament we played in. Plenty of room, everything was great."
United States
Jeffrey R.
The price is AU$166
includes taxes & fees
16 Nov - 17 Nov
Cozy loft above ink shop

Country Get Away 1 Bedroom Apartment

Elkton
9.8 out of 10, Exceptional, (40)
"The hosts were amazing and enjoyed talking with them. We look forward to coming back soon. Sean and Paula "
United States
Michael B.
The price is AU$174
includes taxes & fees
24 Nov - 25 Nov
Country Get Away 1 Bedroom Apartment

Private townhouse near downtown and state park

Downtown Wilmington
9.4 out of 10, Exceptional, (11)
"Property was extremely clean!"
United States
margaret p.
The price is AU$436
includes taxes & fees
17 Nov - 18 Nov
Private townhouse near downtown and state park

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

Newark
9.8 out of 10, Exceptional, (19)
"This place is beautiful in a quiet neighborhood. The kitchen is well stocked, the bed are so comfortable and the bathrooms are very nice, especially the master bath!!! I'd definitely stay here again."
United States
Lisa Y.
The price is AU$517
includes taxes & fees
15 Nov - 16 Nov
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

New Construction townhome close to everything downtown w/transparent pricing

Wilmington
9.8 out of 10, Exceptional, (19)
"Beautiful home. Lisa was so lovely to specially set up a room for my 86 year old mother! We would not hesitate to stay again!!"
United States
becky m.
The price is AU$317
includes taxes & fees
16 Nov - 17 Nov
New Construction townhome close to everything downtown w/transparent pricing

Charming Carriage House in the Heart of Kennett

Kennett Square
10.0 out of 10, Exceptional, (37)
"Lovely property in downtown Kennett Square. Plenty of room and comfortable furniture. Bath has been updated beautifully. It is important to note that the loft is accessed by a steep ladder. The ladder appears to be very sturdy, but could be challenging for someone with mobility issues. Lots of places to walk the dog. We will stay here again!"
United States
Anonymous traveller
The price is AU$686
includes taxes & fees
16 Nov - 17 Nov
Charming Carriage House in the Heart of Kennett

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"The dome and surrounding areas looks like it does in the photos, and using the compost toilet, shower, etc were pretty easy even for a camping novice like myself. The farm is beautiful and quiet. Good opportunities for birding too. I never saw or heard the gentlemen who live in the farmhouse, I only saw their cars come and go. I came here for rest and a connection to nature, and that’s what I got. I’d love to come back in the future! I think it would be even nicer later in the spring."
United States
Lady N.
The price is AU$251
includes taxes & fees
16 Nov - 17 Nov
Summer Rustic Camping with AC and King Bed

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Elkton
8.0 out of 10, Very good, (9)
"Beautiful location in the middle of Elk Neck State Park. We slept comfortably and enjoyed our stay. Heads up for travelers (esp city folk!) with small children, don’t forget the tick repellent. We found one on our son who had played in the yard for a short time. "
United States
NEB 7.
The price is AU$435
includes taxes & fees
18 Nov - 19 Nov
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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, 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 favourite 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 depend 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 AU$194 per night. Entering your travel dates in the search wizard might find you 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

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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Winchester is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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. Historical Society of Cecil County and University of Delaware 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.