Winchester Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Winchester

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD

$527 nightly

$559 total

Mar 26 - Mar 27

Total with taxes and fees

Located in Perryville, this vacation home is on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Craft Haven Marina.

Kitchen

Washer

Lancaster co. farmhouse in the heart of amish country

Christiana PA

Located in Kirkwood, this vacation home is in a rural location, within a 15-minute drive of Wolf's Hollow Park and Moccasin Run Golf Course.

Kitchen

Washer

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Chesapeake City MD

With a stay at this vacation home in Chesapeake City, you'll be just steps from Ferryslip Road Park and Chesapeake City Town Hall.

Pool

Hot Tub

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square PA

$421 nightly

$465 total

Mar 11 - Mar 12

Total with taxes and fees

With a stay at this vacation home in Kennett Square, you'll be within a 10-minute drive of Longwood Gardens and Anson B. Nixon Park.

Washer

Dryer

Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle DE

$280 nightly

$291 total

Mar 25 - Mar 26

Total with taxes and fees

With a stay at this vacation home in New Castle, you'll be within a 15-minute drive of Christiana Mall and Dragon Run Park.

Kitchen

Washer

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Wilmington DE

$124 nightly

$129 total

Mar 11 - Mar 12

Total with taxes and fees

With a stay at this vacation home in Wilmington (South Wilmington), you'll be within a 15-minute drive of Wilmington Riverwalk and Christiana Mall.

Kitchen

Washer

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton MD

Located in Elkton, this vacation home is a 3-minute drive from Upper Bay Museum and 6 minutes from Milburn Stone Theater.

Kitchen

Washer

Underground Railroad Barn

Kennett Square PA

$253 nightly

$287 total

Mar 11 - Mar 12

Total with taxes and fees

With a stay at this vacation home in Kennett Square, you'll be within a 10-minute drive of Longwood Gardens and Anson B. Nixon Park.

Kitchen

Washer

Chesapeake Bay House with Dock & Private Beach

Elkton MD

Located in Elkton, this vacation home is on the waterfront, within a 15-minute drive of Chesland Park and Chesapeake City Bridge.

Kitchen

Washer

New Construction townhome close to everything downtown w/transparent pricing

Wilmington DE

With a stay at this vacation home in Wilmington (Hilltop), you'll be within a 15-minute drive of Wilmington Riverwalk and Christiana Mall.

Kitchen

Air conditioning

Spring Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City MD

With a stay at this vacation home in Chesapeake City, you'll be within a 5-minute drive of Chesapeake City Bridge and South Chesapeake City Historic District.

Kitchen

Washer

Nancy’s Touch, A Waterfront Paradise!

North East MD

Located in North East, this vacation home is on the waterfront, within a 10-minute drive of Roachs Shore and Elk Neck State Park.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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.