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Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
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Nov 21 - Nov 23
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Dec 19 - Dec 21

Cottages in Chesapeake City

Our top choices for Chesapeake City cottages

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

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

10.0 out of 10, Exceptional, (22)
"Very nice cottage, as advertised"
The price is ￥25,965
￥31,130 total
includes taxes & fees
Sep 24 - Sep 25
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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 ￥32,663
￥73,695 total
includes taxes & fees
Sep 23 - Sep 24
Thunder Hill Retreat - Spacious/Deck/Hot tub
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Outdoor dining

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

10.0 out of 10, Exceptional, (9)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
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 💙"
The price is ￥19,707
￥31,553 total
includes taxes & fees
Sep 23 - Sep 24
Quarry Landing - Center of Town & River View - 3 Bedroom
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Terrace/patio

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
Cozy Cottage on the North East River in Town!
Exterior

Cozy Cottage on the North East River in Town!

10.0 out of 10, Exceptional, (1)
"Super clean, great location, host communication was top tier, house was fully stocked, and bird watching by the river was fantastic "
Cozy Cottage on the North East River in Town!
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
Exterior

Waterfront cottage in historic Charlestown, Maryland

9.8 out of 10, Exceptional, (10)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Outdoor dining

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (56)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Eastern shore beachfront cottage with stunning sunset views!
Interior

Eastern shore beachfront cottage with stunning sunset views!

10.0 out of 10, Exceptional, (2)
"Our family had a great time at the cottage. It is very well appointed and a great place to connect with family. They kayaks were fun to use and we caught a catfish right from the bank. "
Eastern shore beachfront cottage with stunning sunset views!
A cottage on the shore of the Delaware River
Exterior

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!
Exterior

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!
Charming 2-bedroom water oriented cottage with water access
Exterior

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
Hill Top Cottage with Chickens!
Exterior

Hill Top Cottage with Chickens!

10.0 out of 10, Exceptional, (11)
"We loved it and would recommend to anyone looking for a quick getaway."
Hill Top Cottage with Chickens!
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

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!"
The price is ￥53,218
￥80,459 total
includes taxes & fees
Oct 6 - Oct 7
Long Beach Cottage, (romantic couple’s getaway)
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Exterior

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
Grandma’s Cottage will wrap around you like a warm hug
Exterior

Grandma’s Cottage will wrap around you like a warm hug

The price is ￥33,289
￥60,849 total
includes taxes & fees
Sep 23 - Sep 24
Grandma’s Cottage will wrap around you like a warm hug
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

Hyatt Place Wilmington Riverfront

Hyatt Place Wilmington Riverfront

10/10 Excellent
"We had a really nice stay at this hotel. The highlight was the beautiful riverfront right behind the property — a peaceful walk surrounded by flowers and greenery that made the whole area feel so relaxing. There were also a few restaurants within walking distance, which made it super convenient. The combination of comfort at the hotel and the lovely surroundings made it a great experience. The staff was also very attentive and super friendly! We’d definitely stay here again!"
Maryanne 2-night trip
Posted 3 days ago
Hyatt Place Wilmington Riverfront

Find out more about Chesapeake City

Find out more about Chesapeake City

Chesapeake City Cottages information

Number of reviews
231
Accommodation
32 Cottages
Lowest Price
￥31,130
Highest Price
￥80,459

Frequently asked questions

Why book your cottage in Chesapeake City with Expedia?
Booking a cottage in Chesapeake City is as easy as working out your travel dates and selecting your ideal place for a vacation in nature. From upmarket retreats to budget-friendly stays and cottages that include amenities like a kitchenette, Expedia has something for all traveler tastes. As for epic deals? We've got them too!
How can I find cheap cottages in Chesapeake City?
With Expedia's filter tool, comparing cheap cottages in Chesapeake City is easy. To find properties that are friendly on the wallet, fine-tune your search results by budget, star rating and amenities.
What is there to do in Chesapeake City near my cottage?
The perfect travel accessory is a well-planned schedule. Bohemia Vista Marina is an excellent place to kick-start your adventures in Chesapeake City.

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Explore a world of travel with Expedia