Winchester Holiday Rentals

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Holiday Rentals in Winchester

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm

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

10.0 out of 10, Exceptional, (25)
"Very nice cottage, as advertised"
The price is NZ$359
includes taxes & fees
7 Oct - 8 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (173)
"Nice property. Large enough for 13. Plenty of space to spread out "
Chesapeake Bay House with Dock & Private Beach

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

9.4 out of 10, Exceptional, (33)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

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

9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
The price is NZ$571
includes taxes & fees
7 Oct - 8 Oct
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"Everything about this rental was easy, from check in to departure. We had one challenge with the TV and the host answered my text immediately and solved the issue for us. House was clean and as described in the listing. Highly recommend. "
Waterfront house with amazing views. Top of the Chesapeake

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is NZ$478
includes taxes & fees
7 Oct - 8 Oct
Historic Chesapeake City Stay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (170)
"Absolutely fantastic place to stay. When we walked in, it just felt so comfortable. The gardens are beautiful and we were able to see Eagles most every day. Communication was excellent. "
Nancy’s Touch, A Waterfront Paradise!

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (81)
"One of the nicest properties we have stayed at. Fantastic amenities. Highly recommend!!"
The price is NZ$656
includes taxes & fees
7 Oct - 8 Oct
Homey Retreat in Historic Kennett Square!!

Charming Carriage House in the Heart of Kennett

10.0 out of 10, Exceptional, (36)
"We had a lovely visit! Communication was great, the place was clean, comfortable, and well stocked. Highly recommend!"
The price is NZ$747
includes taxes & fees
7 Oct - 8 Oct
Charming Carriage House in the Heart of Kennett

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (48)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (3)
"Wonderful property. The owners went above and beyond to make us feel at home and to make a special celebration more memorable. The hose has charm, both inside and out. We enjoyed the four nights and will definitely be staying again. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (276)
"We had such a great weekend at this property. It was beautiful and such a relaxing location. House had everything we needed. We hope to be back!! "
Captivating Chesapeake experience

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (145)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is NZ$1,031
includes taxes & fees
15 Oct - 16 Oct
5-bedroom vacation home 5 minutes from historic Charlestown

Tiny Home Tranquil Oasis

The price is NZ$414
includes taxes & fees
7 Oct - 8 Oct
Tiny Home Tranquil Oasis

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is NZ$277
includes taxes & fees
7 Oct - 8 Oct
Summer Rustic Camping with AC and King Bed

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

9.8 out of 10, Exceptional, (10)
"We thoroughly enjoyed this cottage and location for weekend during lacrosse tournaments. Much better than staying in hotel and perfect on the water to enjoy some family time! Thanks Angela! "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

2.0 star property
9.6 out of 10, Exceptional, (9)
"We had an excellent stay"
The price is NZ$400
includes taxes & fees
8 Oct - 9 Oct
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Charming apartment in serene Wilmington with AC

8.0 out of 10, Very good, (1)
"The host and actual apartment are great - clean, nice bathroom, the host was so friendly and left amazing treats, including a surprise for breakfast. The neighborhood was not great, and unfortunately was the only bad part about this stay. Otherwise I'd give 5 stars and would definitely stay with this host again."
The price is NZ$213
includes taxes & fees
13 Oct - 14 Oct
Charming apartment in serene Wilmington with AC
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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Top Winchester Hotel Reviews

Find out more about Winchester

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$213 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

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. 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.