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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Cottages in Chesapeake City

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, (20)
"Very nice cottage, as advertised"
The price is AU$327
includes taxes & fees
4 Sept - 5 Sept
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

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
Smart TV, books

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
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Fireplace

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (12)
"Great location right on the water. Great for fishing or just sitting and relaxing. The house is in a quiet secluded area but only 10 minutes from Chesapeake Bay. Pool was an awesome extra. My son enjoyed it. The home was clean and plenty of space. "
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Sunset River Shack -amazing waterfront view
Property grounds

Sunset River Shack -amazing waterfront view

2.0 star property
9.4 out of 10, Exceptional, (3)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
Sunset River Shack -amazing waterfront view
Waterfront cottage in historic Charlestown, Maryland
Interior

Waterfront cottage in historic Charlestown, Maryland

9.8 out of 10, Exceptional, (9)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
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, (7)
"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 💙"
The price is AU$430
includes taxes & fees
2 Sept - 3 Sept
Quarry Landing - Center of Town & River View - 3 Bedroom
Eastern shore beachfront cottage with stunning sunset views!
Interior

Eastern shore beachfront cottage with stunning sunset views!

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Eastern shore beachfront cottage with stunning sunset views!
A cottage on the shore of the Delaware River
On the beach

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (65)
"This small home was perfect for a stay on our road trip. Beautiful views and quiet place to stay."
A cottage on the shore of the Delaware River
Waterfront Cottage on the C&D Canal!
Fridge, microwave, oven, stovetop

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!
Walk to Town & River: Charming Home in North East!
House (3 Bedrooms) | Interior

Walk to Town & River: Charming Home in North East!

3.0 star property
Walk to Town & River: Charming Home in North East!
Thunder Hill Retreat - Spacious/Deck/Hot tub
Outdoor spa tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (14)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
The price is AU$745
includes taxes & fees
2 Sept - 3 Sept
Thunder Hill Retreat - Spacious/Deck/Hot tub
Vintage Waterfront Cottage with Stunning Sunsets
Terrace/patio

Vintage Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (5)
"This was a perfect spot for a quick getaway for my husband and I! The house is lovely with plenty of charm, a well-appointed kitchen and comfortable furniture. The yard is lovely and it’s just a short walk to the private beach to bird watch or just take a stroll. Would highly recommend!"
Vintage Waterfront Cottage with Stunning Sunsets
Charming 2-bedroom water oriented cottage with water access
Marina

Charming 2-bedroom water oriented cottage with water access

10.0 out of 10, Exceptional, (1)
"This adorable cottage provided the perfect atmosphere for a week long getaway. The kitchen was immaculate and the center island quickly became our favorite place to sip our morning coffee. The bathroom was roomy with a beautiful shower and a large washer and dryer.The host was gracious and left cookies and candy as well as beautiful flowers upon our arrival. If our family is ever visiting the area again, we will definitely stay here!"
Charming 2-bedroom water oriented cottage with water access
Waterfront Historical District Home Near River
House (3 Bedrooms) | Interior

Waterfront Historical District Home Near River

3.0 star property
10.0 out of 10, Exceptional, (2)
"The home was beautiful and well kept. Essential kitchen items are included along with sheets and towels. The host was a super reliable. Communication was wonderful. The host had toiletries and some stocked snacks for the guests. There were corn hole boards and ladder ball for guests to use. The home is about a block to the river where fishing is a must. There is also a public beach within walking distance. "
Waterfront Historical District Home Near River
Long Beach Cottage, (romantic couple’s getaway)
Terrace/patio

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
Long Beach Cottage, (romantic couple’s getaway)
Family-Friendly Cottage, Walk to the Beach!
Interior

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Great location "
Family-Friendly Cottage, Walk to the Beach!
Hill Top Cottage with Chickens!
Property grounds

Hill Top Cottage with Chickens!

10.0 out of 10, Exceptional, (10)
"We loved it and would recommend to anyone looking for a quick getaway."
Hill Top Cottage with Chickens!
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Marina

3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor

9.4 out of 10, Exceptional, (6)
"Thanks Gwendolyn… we had a great time!"
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.2 out of 10, Wonderful, (10)
"Had a lovely peaceful stay. Great amenities."
Be persuaded to experience this vintage cottage by the Sassa
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 Chesapeake City Hotel Reviews

Find out more about Chesapeake City

Find out more about Chesapeake City

Chesapeake City Cottages information

Number of reviews
136
Accommodation
33 Cottages
Lowest Price
AU$327
Highest Price
AU$745

Frequently asked questions

What is there to do in Chesapeake City near my cottage?
Chesapeake City has enough experiences to keep you on the hop for weeks, starting with Historical Society of Cecil County. Bohemia Vista Marina, East Meadow Park and Patriots Glen Golf Club are other renowned attractions. If you're lingering longer, Elkton Golf and Batting Centre and Cow Pond are worthwhile additions to your itinerary.