Winchester Vacation Rentals

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Check prices for these dates

Tonight
Jan 13 - Jan 14
Tomorrow
Jan 14 - Jan 15
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Our top choices for Winchester vacation rentals

Private kitchen
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
3.0 star property
Trolley Square
6.0 out of 10, (1 review)
"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 P5,236
P17,553 total
includes taxes & fees
Jan 14 - Jan 15
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
Living area
The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning

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
Trolley Square
The price is P6,738
P22,515 total
includes taxes & fees
Jan 21 - Jan 22
The Gilpin Getaway 2br Free Coffee 2 Bedroom Apts by RedAwning
View from property
The Loft At Gilpin Placeking Bedtrolley Square! 1 Bedroom Apts by RedAwning

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
Trolley Square
6.0 out of 10, (1 review)
The price is P6,411
P19,113 total
includes taxes & fees
Jan 21 - Jan 22
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

Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

10/10 Excellent
"Good"
cuihua 18-night trip
Posted 4 days ago
Sonesta Select Newark Christiana Mall

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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Look no further and take a look at our great range of rental properties in Winchester!

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.