Perryville Vacation Rentals

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Vacation Rentals in Perryville

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville MD

When you a stay at this vacation home in Perryville, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Hot Tub

Kitchen

* NEWLY RENOVATED** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville MD

When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Chesapeake Bay.

Hot Tub

Kitchen

Summer 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 Cecil County Public Library Chesapeake City Branch.

Chesapeake Bay House with Dock & Private Beach

Elkton MD

Located in Elkton, this vacation home is on the waterfront, within a 10-minute drive of Chesland Park and Brantwood Park.

Kitchen

Washer

Luxury Waterfront Home Built for Entertaining!

Abingdon MD

$784 nightly

$831 total

Dec 9 - Dec 10

Total with taxes and fees

Located in Abingdon, this vacation home is within a 10-minute drive of Belcamp Beach and Queen Alexandra Hospital Online.

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

Elkton MD

$265 nightly

$281 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Elkton, you'll be within a 15-minute drive of Upper Bay Museum and Elk Neck State Park.

Kitchen

Washer

Modern cozy get-away* game room-amish country

North East MD

Located in North East, this vacation home is a 4-minute drive from Milburn Stone Theater and 5 minutes from Calvert Regional Park.

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Havre De Grace MD

A stay at this vacation home places you in the heart of Havre De Grace, within a 15-minute walk of Susquehanna Museum at the Lock House and Susquehanna River.

Kitchen

Washer

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD

$567 nightly

$601 total

Dec 10 - Dec 11

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

Summer Rustic Camping with AC and King Bed

Elkton MD

$178 nightly

$179 total

Jan 8 - Jan 9, 2026

Total with taxes and fees

With a stay at this vacation home in Elkton, you'll be within a 15-minute drive of University of Delaware and Fair Hill Equestrian Center.

Waterfront house with amazing views. Top of the Chesapeake

Perryville MD

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.

Captivating Chesapeake experience

Perryville MD

When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 5-minute drive of Chestnut Point Estates and Marina and Chesapeake Bay.

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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.