Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Rentals in Winchester

Apartment, 1 Bedroom | Private kitchen | Fridge, coffee/tea maker
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
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...
The price is NT$2,741
NT$8,575 total
includes taxes & fees
Oct 16 - Oct 17
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
Apartment, 1 Bedroom | Private kitchen | Fridge, coffee/tea maker
Gilpin Grand - Renovated Space In Trolley Square 1 Bedroom Apts by RedAwning
Gilpin Grand - Renovated Space In Trolley Square 1 Bedroom Apts by RedAwning
3.0 star property
The price is NT$3,235
NT$9,174 total
includes taxes & fees
Oct 19 - Oct 20
Gilpin Grand - Renovated Space In Trolley Square 1 Bedroom Apts by RedAwning
Apartment, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker
The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning
The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning
3.0 star property
The price is NT$3,561
NT$11,055 total
includes taxes & fees
Oct 21 - Oct 22
The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning
Apartment, 1 Bedroom | Living area
The Loft At Gilpin Placeking Bedtrolley Square! 1 Bedroom Apts by RedAwning
The Loft At Gilpin Placeking Bedtrolley Square! 1 Bedroom Apts by RedAwning
3.0 star property
6.0 out of 10, (1)
The price is NT$3,376
NT$9,346 total
includes taxes & fees
Oct 16 - Oct 17
The Loft At Gilpin Placeking Bedtrolley Square! 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

Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

10/10 Excellent
"Very pleasant place to stay"
REMONA 6-night trip
Posted 1 day ago
Baymont by Wyndham Newark at University of Delaware

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Winchester?

Yes, you can find vacation rentals near top local attractions in Winchester, or you can go with a 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 larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private accommodations you can stay in for several days or longer in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.