Search Holiday Rentals in Winchester

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Winchester holiday rentals

Apartment, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker
The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning

Apartment in Trolley Square

The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning
3.0 star property
The price is 3.132.814 ₫
9.686.027 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning
Apartment, 1 Bedroom | Private kitchen | Fridge, coffee/tea maker
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Apartment in Trolley Square

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
3.0 star property
6.0 out of 10, (1)
"Be aware that there is on street parking that requires a permit from the city of Wilmington. Red Awni ng worked with me to resolve the issue but it took some time and a few texts to make it work.The on street parking placed me a block and half from the propery. No cost but need proof of renting the space. The GPS sent you down a one way street that does not bring by the front of the property. This was a problem finding the property after dark. No climate control of the rental unit. The bed was...
United States
Clifford
The price is 2.416.630 ₫
7.529.775 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
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

Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront

10/10 Excellent
"Yes"
Garnell 1-night trip
Posted 3 days ago
Woodspring Suites Wilmington Riverfront

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 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.