Perry Point Holiday Rentals

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Holiday Rentals in Perry Point

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is AU$434
includes taxes & fees
28 Aug - 29 Aug
Historic Chesapeake City Stay

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is AU$1,005
includes taxes & fees
8 Sept - 9 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.2 out of 10, Wonderful, (5)
The price is AU$491
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom cabin close to Fair Hill on horse farm

Sailor's Sunrise Cottage - Chesapeake Bay

9.6 out of 10, Exceptional, (51)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

10.0 out of 10, Exceptional, (20)
"Very nice cottage, as advertised"
The price is AU$328
includes taxes & fees
1 Sept - 2 Sept
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

2.0 star property
9.4 out of 10, Exceptional, (6)
"We had an excellent stay"
The price is AU$365
includes taxes & fees
1 Sept - 2 Sept
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

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

9.6 out of 10, Exceptional, (61)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (7)
"Can’t say enough about how nice this place is. We had quick friendly responses from owners. Very clean and the water front view was excellent. Highly recommended "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

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

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

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

9.4 out of 10, Exceptional, (30)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

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

9.2 out of 10, Wonderful, (179)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (45)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (166)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

9.8 out of 10, Exceptional, (17)
"Enjoyed our stay. Location is beautiful and peaceful! Great place for a large group."
Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is AU$272
includes taxes & fees
1 Sept - 2 Sept
Summer Rustic Camping with AC and King Bed

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (272)
"Beautiful home and setting!"
Captivating Chesapeake experience
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 Perry Point Hotel Reviews

Find out more about Perry Point

Find out more about Perry Point

Everything you need to know about Perry Point holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Perry Point holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Perry Point holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Perry Point holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Perry Point. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Perry Point holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Perry Point holiday rentals we have selected for you start as low as AU$272 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Perry Point rentals

At Expedia, we put the best Perry Point holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Perry Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Perry Point holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Perry Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Perry Point?

Yes, there are holiday rentals close to the most popular sights in Perry Point, or you can select a more secluded option if you're looking for a relaxing stay.

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

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Perry Point is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Perry Point?

While exploring the area, visit family-friendly sights like Havre de Grace Maritime Museum, or get outside and enjoy nature at Garrett Island Beach. Concord Point Lighthouse and Havre de Grace Decoy Museum are a couple of places you'll find in the wider area.

What are holiday rentals like in Perry Point?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Perry Point. Holiday rentals feature extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips or small group gatherings.