Search Holiday Rentals in Winchester

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Top Holiday Rentals in Winchester

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 £228
includes taxes & fees
7 Jul - 8 Jul
Private townhouse near downtown and state park

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 £595
includes taxes & fees
14 Jul - 15 Jul
Entire two-unit four-story townhouse, for multi-family vacations; free parking

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

2.0 star property
The price is £211
includes taxes & fees
8 Jul - 9 Jul
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

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 £181
includes taxes & fees
7 Jul - 8 Jul
New Construction townhome close to everything downtown w/transparent pricing

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 £273
includes taxes & fees
9 Jul - 10 Jul
Charming and Cozy 3-bedroom Row Home - Ideal for Students, Travelers & Families!

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 £265
includes taxes & fees
7 Jul - 8 Jul
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

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 £235
includes taxes & fees
13 Jul - 14 Jul
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Underground Railroad 4 Bedroom Farmhouse

9.8 out of 10, Exceptional, (18)
"Great property for a girls' weekend. Super clean, helpful and friendly owner, cute property and grounds, well-maintained."
The price is £215
includes taxes & fees
10 Jul - 11 Jul
Underground Railroad 4 Bedroom Farmhouse

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 £232
includes taxes & fees
28 Jul - 29 Jul
Underground Railroad Barn

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (76)
"So convenient and easy to walk to shops and food! The house is adorable and clean. Looking forward to staying again. "
The price is £246
includes taxes & fees
14 Jul - 15 Jul
Homey Retreat in Historic Kennett Square!!

The Historic Walton House by RPG

10.0 out of 10, Exceptional, (33)
"This house made visiting my dad recovering from a medical procedure feel more of a "vacation" for my pre teen and teen kids. Exactly what we were looking for."
The price is £506
includes taxes & fees
8 Jul - 9 Jul
The Historic Walton House by RPG

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 £374
includes taxes & fees
7 Jul - 8 Jul
Kennett Square, Near Longwood Gardens & Downtown

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 £393
includes taxes & fees
8 Jul - 9 Jul
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

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

9.6 out of 10, Exceptional, (5)
The price is £260
includes taxes & fees
9 Jul - 10 Jul
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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 £125
includes taxes & fees
7 Jul - 8 Jul
Summer Rustic Camping with AC and King Bed

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 £453
includes taxes & fees
15 Jul - 16 Jul
5-bedroom vacation home 5 minutes from historic Charlestown

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 £175
includes taxes & fees
7 Jul - 8 Jul
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

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

9.4 out of 10, Exceptional, (3)
"Beautiful house with lots of space for a family gathering. After a couple very hot days at Ripken (only 15 minute drive) the kids enjoyed cooling off in the pool and playing in the large yard. Would definitely stay again! "
The price is £899
includes taxes & fees
6 Jul - 7 Jul
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Quiet house heated pool & waterfall open all year

10.0 out of 10, Exceptional, (3)
"We stayed there over valentines weekend. Home was very well taken care out. Very clean. The heated pool is amazing. We were able to swim with snow on the ground. Plenty of room. Bathroom is beautiful. Homeowner communicated well and I can’t express enough how much we loved this place e and hope to come back again soon. It’s only 15 minutes away from Conowingo Dam to see all the bald eagles. Also within 10 minutes of grocery stores and food establishments. "
The price is £336
includes taxes & fees
8 Jul - 9 Jul
Quiet house heated pool & waterfall open all year
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?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Winchester is located on a lake, and has a patio, a garden and a BBQ to put you at ease 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. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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.