Perry Point Vacation Rentals

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Oct 12 - Oct 13
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Oct 24 - Oct 26

Vacation Rentals in Perry Point

Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (173)
"Nice property. Large enough for 13. Plenty of space to spread out "
Chesapeake Bay House with Dock & Private Beach
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV, books

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

10.0 out of 10, Exceptional, (25)
"Very nice cottage, as advertised"
$200 nightly
The price is $211
Oct 20 - Oct 21
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Waterfront house with amazing views. Top of the Chesapeake
Terrace/patio

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
Waterfront house with amazing views. Top of the Chesapeake
Nancy’s Touch, A Waterfront Paradise!
Terrace/patio

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (171)
"The house was quaint, scenic, well maintained and in a great location with a breathtaking view of the bay. We had a wonderful time there, would definitely recommend it and would love to revisit again. "
Nancy’s Touch, A Waterfront Paradise!
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (50)
"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
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

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

9.8 out of 10, Exceptional, (10)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Restful Non-Shared Basement Suite In Harford MD
1 bedroom, WiFi, bed sheets, wheelchair access

Restful Non-Shared Basement Suite In Harford MD

$105 nightly
The price is $111
Oct 19 - Oct 20
Total with taxes and fees
Restful Non-Shared Basement Suite In Harford MD
Historic Chesapeake City Stay
Marina

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
$263 nightly
The price is $279
Oct 13 - Oct 14
Total with taxes and fees
Historic Chesapeake City Stay
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, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

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

9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Marina

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Terrace/patio

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (3)
"Wonderful property. The owners went above and beyond to make us feel at home and to make a special celebration more memorable. The hose has charm, both inside and out. We enjoyed the four nights and will definitely be staying again. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Exterior

Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (94)
"The properly is in great shape, clean and well provisioned. The flat back yard is perfect for yard games and when the tide is low, there a little private beach! The kids played in the sand and floated around Still Pound Creek all weekend. Loretta was an excellent host!"
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
$282 nightly
The price is $311
Oct 13 - Oct 14
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
5-bedroom vacation home 5 minutes from historic Charlestown
Sun loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (145)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
$567 nightly
The price is $601
Oct 15 - Oct 16
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Summer Rustic Camping with AC and King Bed
1 bedroom

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (5)
"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."
$181 nightly
The price is $182
Nov 3 - Nov 4
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
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, (41)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds

Quarry Landing - Center of Town & River View - 3 Bedroom

9.8 out of 10, Exceptional, (9)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
$201 nightly
The price is $213
Nov 3 - Nov 4
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
High Tide Haven Suite
1 bedroom, iron/ironing board, WiFi, bed sheets

High Tide Haven Suite

$194 nightly
The price is $201
Oct 13 - Oct 14
Total with taxes and fees
High Tide Haven Suite
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

La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton

10/10 Excellent
"Good coffee and nice room"
Kalina 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Newark - Elkton

Find out more about Perry Point

Everything you need to know about Perry Point vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Perry Point vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Perry Point vacation 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 low season months. For more hustle and bustle, you may prefer to visit Perry Point in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Perry Point rentals

At Expedia, we put the best Perry Point vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Perry Point?

Yes, we have vacation rentals near well known attractions in Perry Point, or you can select a secluded option if you're looking for a relaxing stay.

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

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Perry Point is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 larger area.

What are vacation rentals like in Perry Point?

Vacation rentals are private properties you can book for a couple days or more in Perry Point. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.