Winchester Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winchester

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"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 AU$270
includes taxes & fees
18 July - 19 July
Summer Rustic Camping with AC and King Bed

Underground Railroad Barn

9.8 out of 10, Exceptional, (15)
"The barn was lovely and great location! The owner was easy to reach with any question I had. "
The price is AU$486
includes taxes & fees
5 Aug - 6 Aug
Underground Railroad Barn

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had an excellent stay"
The price is AU$367
includes taxes & fees
29 July - 30 July
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great outdoor space "
The price is AU$480
includes taxes & fees
21 July - 22 July
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Charming and Cozy 3-bedroom Row Home - Ideal for Students, Travelers & Families!

8.8 out of 10, Excellent, (3)
"We needed a place to accommodate our family for a stay to visit family. House was very clean and listing was accurate. 3 bedroom was a pull out futon. Parking was off-street. "
The price is AU$567
includes taxes & fees
27 July - 28 July
Charming and Cozy 3-bedroom Row Home - Ideal for Students, Travelers & Families!

Kennett Square, Near Longwood Gardens & Downtown

7.8 out of 10, Good, (10)
"Great place, very difficult check in process. It was a nice stay overall "
The price is AU$777
includes taxes & fees
20 July - 21 July
Kennett Square, Near Longwood Gardens & Downtown

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

9.6 out of 10, Exceptional, (4)
"This property was amazing! My family of six, really enjoyed the pool, large yard, for one including a balcony, toys for the kids, and many more! Will definitely be staying again in the future"
The price is AU$1,798
includes taxes & fees
21 July - 22 July
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

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

9.8 out of 10, Exceptional, (18)
"We rented this townhouse for a month for my son's surgical residency rotation at Cristiana Care. It was a perfect location and easy to get to and from the hospital. Owner was very responsive with any questions / concerns which we appreciated. Very quiet and close to grocery stores. Even had a Trader Joe's close by!"
The price is AU$541
includes taxes & fees
21 July - 22 July
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

2.0 star property
The price is AU$424
includes taxes & fees
21 July - 22 July
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

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

8.4 out of 10, Very good, (6)
"Very Nice!"
The price is AU$548
includes taxes & fees
3 Aug - 4 Aug
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Underground Railroad 4 Bedroom Farmhouse

9.8 out of 10, Exceptional, (19)
"Great property for a girls' weekend. Super clean, helpful and friendly owner, cute property and grounds, well-maintained."
The price is AU$616
includes taxes & fees
3 Aug - 4 Aug
Underground Railroad 4 Bedroom Farmhouse

The Historic Walton House by RPG

10.0 out of 10, Exceptional, (33)
"Very convenient location and well-appointed unit. "
The price is AU$1,019
includes taxes & fees
22 July - 23 July
The Historic Walton House by RPG

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (77)
"So convenient and easy to walk to shops and food! The house is adorable and clean. Looking forward to staying again. "
The price is AU$522
includes taxes & fees
22 July - 23 July
Homey Retreat in Historic Kennett Square!!

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AU$947
includes taxes & fees
21 July - 22 July
5-bedroom vacation home 5 minutes from historic Charlestown

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is AU$465
includes taxes & fees
28 July - 29 July
Private townhouse near downtown and state park

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
The price is AU$803
includes taxes & fees
22 July - 23 July
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Entire two-unit four-story townhouse, for multi-family vacations; free parking

9.6 out of 10, Exceptional, (9)
"An excellent stay once again. Our host was friendly and the house was amazing per usual. Thank you!"
The price is AU$1,227
includes taxes & fees
29 July - 30 July
Entire two-unit four-story townhouse, for multi-family vacations; free parking

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (17)
"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!!"
The price is AU$372
includes taxes & fees
12 Aug - 13 Aug
New Construction townhome close to everything downtown w/transparent pricing
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.
Save an average of 15% on thousands of hotels when you're signed in

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.