Book Holiday Homes in Perryville

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Featured Holiday Homes in Perryville

Chesapeake City Quiet Overlook

Chesapeake City Quiet Overlook

Chesapeake City
Located in Chesapeake City, this vacation home is on the waterfront, within a 10-minute drive of C and D Canal Museum and Lums Pond State Park.
Chesapeake City Quiet Overlook
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Luxurious and spacious townhome with all necessary amenities awaits your stay.

Middletown
Located in Middletown, this vacation home is within a 5-minute drive of Dutch Country Farmers Market and Appoquinimink Friends Meeting House.
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
Located in Elkton, this vacation home is a 3-minute drive from Upper Bay Museum and 6 minutes from Milburn Stone Theater.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
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Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Perryville
Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Hollywood Casino.
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton
When you stay at this vacation home in Betterton, you'll be on the waterfront and 7 minutes by foot from Betterton Beach.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Amazing Waterfront Home on the Bush River

Amazing Waterfront Home on the Bush River

Edgewood
When you stay at this vacation home in Edgewood, you'll be on the waterfront and 9 minutes by car from CopperPlex.
Amazing Waterfront Home on the Bush River
Baseball Lovers Paradise!

Baseball Lovers Paradise!

Aberdeen
Located in Aberdeen, this vacation home is within a 5-minute drive of Cal Ripken Museum and Ripken Stadium.
Baseball Lovers Paradise!
Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"

Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"

Delta
Located in Delta, this vacation home is on the waterfront, within a 15-minute drive of Guppy Gulch Quarry and Holtwood Dam Whitewater Park.
Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"
Upper Chesapeake Getaway - Newly Renovated

Upper Chesapeake Getaway - Newly Renovated

Perryville
Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Hollywood Casino.
Upper Chesapeake Getaway - Newly Renovated
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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.

Perryville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Perryville vacation homes are the perfect way for you to wing it.

Holiday houses in Perryville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Perryville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Perryville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Perryville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Perryville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Perryville Holiday Homes essential information

Accommodation
92 Holiday Homes
Lowest Price
AU$428
Highest Price
AU$739
Popular accommodation
Chesapeake City Quiet Overlook, Luxurious and spacious townhome with all necessary amenities awaits your stay., Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio, Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach, Amazing Waterfront Home on the Bush River, Baseball Lovers Paradise!, Historic Ox Bow House c.1800 "The Cabin at Muddy Creek" , Upper Chesapeake Getaway - Newly Renovated

Top trending hotels in Perryville

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway, Perryville, MD
Fully refundableReserve now, pay when you stay
The price is AU$428 per night from 5 Jan to 6 Jan
AU$428
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Perryville, Great Wolf Lodge Perryville is a 1-minute drive from Hollywood Casino and 5 minutes from Susquehanna State Park.
Great Wolf Lodge Perryville
Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake

Perryville
Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Upper Bay Museum.
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Perryville
Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Hollywood Casino.
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Save an average of 15% on thousands of hotels when you're signed in
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
The price is AU$739 per night from 12 Jan to 13 Jan
AU$739
includes taxes & fees
12 Jan - 13 Jan 2025
Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Upper Bay Museum.
5-bedroom vacation home 5 minutes from historic Charlestown
Don't see what you're looking for?
See all available properties in Perryville
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.