Perryville Holiday Rentals

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Holiday Rentals in Perryville

Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun-loungers, beach towels

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Property grounds

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

9.8 out of 10, Exceptional, (40)
"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Top of the Chesapeake - Minutes from Historic Charlestown
View from property

Top of the Chesapeake - Minutes from Historic Charlestown

9.8 out of 10, Exceptional, (135)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is AU$1,016
includes taxes & fees
2 Dec - 3 Dec
Top of the Chesapeake - Minutes from Historic Charlestown
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
Exterior

Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

10.0 out of 10, Exceptional, (236)
"This was our second time staying at the property in Drumore. Everyone had a great time and enjoyed our stay. "
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Pet-Friendly Delta Cabin w/ Private Hot Tub!
Terrace/patio

Pet-Friendly Delta Cabin w/ Private Hot Tub!

10.0 out of 10, Exceptional, (22)
"My husband and I wanted a private location we could relax at and were not disappointed. The cabin was very clean, nicely furnished, and was everything we were looking for. The coffee bar was a very nice addition. The hot tub was clean and extremely relaxing as well. We had never played pickle ball but how can you say no to a private court! We would definitely stay again and would highly recommend!!"
Pet-Friendly Delta Cabin w/ Private Hot Tub!
Historic home in the heart of Main Street- walkable to shops and restaurants
Interior

Historic home in the heart of Main Street- walkable to shops and restaurants

10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
The price is AU$716
includes taxes & fees
2 Dec - 3 Dec
Historic home in the heart of Main Street- walkable to shops and restaurants
Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (10)
"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."
Stunning waterfront villa with indoor pool and kids swing set and play area.
Beautiful Colonial Style Home in Nottingham PA
Fridge, microwave, oven, stovetop

Beautiful Colonial Style Home in Nottingham PA

9.8 out of 10, Exceptional, (6)
"Loved the preserved historic quality of the property. So tastefully furnished and lovely. Nice and quiet neighborhood. The exposed beams certainly let you know when someone was in the room over your head but so worth it for the character."
Beautiful Colonial Style Home in Nottingham PA
Amazing Waterfront Home on the Bush River
Terrace/patio

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (18)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun-loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Historic Chesapeake City Stay
Pool

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AU$798
includes taxes & fees
26 Dec - 27 Dec
Historic Chesapeake City Stay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Chesapeake City Quiet Overlook
Outdoor dining

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook
BEACH WITHOUT THE BUSTLE
Beach nearby, sun-loungers, beach towels

BEACH WITHOUT THE BUSTLE

10.0 out of 10, Exceptional, (26)
"We enjoyed our stay. Condo was comfortable and very clean. It provided convenient access for our weekend plans in Kennedyville and Chestertown."
BEACH WITHOUT THE BUSTLE
Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"
Miscellaneous

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

10.0 out of 10, Exceptional, (100)
"House was great, directions were clear and host provided excellent info, property was absolutely beautiful."
Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"
River Haven with Hot Tub | 4 Bed, 3.5 Bath
Terrace/patio

River Haven with Hot Tub | 4 Bed, 3.5 Bath

9.8 out of 10, Exceptional, (22)
"Very secluded and a great house for a family reunion."
River Haven with Hot Tub | 4 Bed, 3.5 Bath
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Outdoor dining

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

9.6 out of 10, Exceptional, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Terrace/patio

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (75)
"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
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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Other types of properties in Perryville you may be interested in

Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun-loungers, beach towels

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Property grounds

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

9.8 out of 10, Exceptional, (40)
"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Top of the Chesapeake - Minutes from Historic Charlestown
View from property

Top of the Chesapeake - Minutes from Historic Charlestown

9.8 out of 10, Exceptional, (135)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is AU$1,016
includes taxes & fees
2 Dec - 3 Dec
Top of the Chesapeake - Minutes from Historic Charlestown
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Frequently asked questions

Can I find holiday rentals in Perryville?

Yes, there are holiday rentals close to the most popular sights in Perryville, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Perryville has a good selection of restaurants. Make sure you have time to check out the riverfront and shopping during your trip.

What are some of the best holiday rentals that Perryville has to offer?

Waterfront house with amazing views. Top of the Chesapeake: This highly rated holiday home rental in Perryville is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Some other homes for rent in Perryville include Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay and Top of the Chesapeake - Minutes from Historic Charlestown.

How many holiday rentals are there in Perryville?

Expedia has 7 holiday rentals for your stay in Perryville.

What can I see and do in Perryville?

Susquehanna River and Garrett Island Beach are a couple of lovely local spots to get outside and enjoy nature. Hollywood Casino and Concord Point Lighthouse are a couple of places you'll find in the wider area.

What are holiday rentals like in Perryville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Perryville. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.