Search Chesapeake City Cottages

Compare 22 Cottages in Chesapeake City with updated reviews, rates, and availability.

Property grounds
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (13)
"The cottage exceeded our expectations. Everything is as pictured. The place is sparkling clean and stocked with everything you need and more. Communication was excellent. Loved the location and the private beach access was a real plus. Great location to use as home base and take day trips in the area."
Family-Friendly Cottage, Walk to the Beach!
Aerial view
Thunder Hill Retreat - Peaceful - sleeps 12
10.0 out of 10, Exceptional, (4)
"Fantastic property, one the the best hosts we have ever had. I would recommend this house and this host to anyone. Above and beyond, we appreciate everything our host did in order for us to enjoy our stay."
The price is $264
$572 total
includes taxes & fees
May 27 - May 28
Thunder Hill Retreat - Peaceful - sleeps 12
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (5)
"What a beautiful home. The host was attentive to the small details in the house, and my friend and I greatly enjoyed our stay."
The price is $209
$306 total
includes taxes & fees
Jun 9 - Jun 10
Quarry Landing - Center of Town & River View - 3 Bedroom
Interior
Chesapeake Romantic Waterfront Home with Private Pool
8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Property grounds
Be persuaded to experience this vintage cottage by the Sassa
9.0 out of 10, Wonderful, (6)
"We planned a 40th birthday get a way for a friend - three couples total stayed at this wonderful home. There was plenty of space for everyone, room to hang out and a great table to playing card games. At first, we were concerned about the shared dock - but there is more than enough room for everyone out there and what a beautiful space it is. We floated in the water each day and prepared meals each night. The kitchen is very well stocked. The house was extremely clean and the hosts are so...
Be persuaded to experience this vintage cottage by the Sassa
Sun loungers, beach towels
Ruby's Sea Glass Cottage near Betterton Beach
10.0 out of 10, Exceptional, (10)
"The property is beautiful."
Ruby's Sea Glass Cottage near Betterton Beach
On the beach
A cottage on the shore of the Delaware River
9.8 out of 10, Exceptional, (54)
"Although weather was unsettled there was still much to do. Home clean and safe."
A cottage on the shore of the Delaware River
Exterior
Private Carriage House Retreat on a 33 Acre Historic Working Estate
10.0 out of 10, Exceptional, (8)
"It was me, my son and my sister staying. The grounds were beautiful, and we fed the goats too! It was late season, so no pool or any relaxing outdoors. Brrr. Traffic is light in the area so it was easy to get in a 2+ mile walk and see the local neighborhoods. As it was mentioned in the listing (but not obvious in the photos), you have to walk through the bunk room to get to the master bedroom, and the door to the upstairs bath doesn't offer total privacy. No place is perfect, and we would...
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Beach nearby, beach towels
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
9.6 out of 10, Exceptional, (15)
"Beautiful river views. Really clean and nicely maintained property. I liked the location which was close to Chesapeake City and reasonable to Elk Neck. We had five and it held us well. It is on the small side but with great outdoor spaces . Hot tub was a nice addition. The host was easy to get a hold of. Wouldn't hesitate to go again"
The price is $295
$464 total
includes taxes & fees
Jun 2 - Jun 3
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
Beach nearby
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.
6.0 out of 10, (1)
"Great location for our weekend. Rental property does not have shampoo or soap as advertised. This was really annoying, we had to run out and get some. There were Ants all over the house, in the kitchen, bathrooms, living room. We even found an ant in our shoe. Also the sheets weren’t that clean. There was hair in between the sheets. I ended up sleeping on the top blanket with a blanket I bought. Also not really 3 bedrooms. The one “bedroom” doesn’t even have a door and opens up to the dining...
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.
Property grounds
Hill Top Cottage with Chickens!
10.0 out of 10, Exceptional, (1)
"The hill top cottage was the perfect space for an eagle watching weekend with my girlfriend’s family! The whole place was as described and very clean. It had all you needed for a stay including cookware, coffee pot, towels, games, and a washer/dryer to dry our jackets after a rainy day. The host was very responsive and kind with any questions or concerns that we had before and during the stay. We had a short power outage due to the storms in the area and the hosts were very helpful and offered...
Hill Top Cottage with Chickens!
Fridge, microwave, oven, stovetop
Waterfront Cottage on the C&D Canal!
8.8 out of 10, Excellent, (3)
"Awesome"
Waterfront Cottage on the C&D Canal!
View from property
Waterfront cottage in historic Charlestown, Maryland
10.0 out of 10, Exceptional, (1)
"A wonderful private location to relax right next to the river. Laura was very quick to respond to our questions and made for a great stay! Will definitely be booking with Laura again"
Waterfront cottage in historic Charlestown, Maryland
Beach nearby, sun loungers, beach towels
Vintage Waterfront Cottage with Stunning Sunsets
10.0 out of 10, Exceptional, (2)
"My wife being a teacher needs a break by October. This vintage waterfront cottage renovated to exacting detail as she watches on her favorite ‘Reno-Shows’ was perfect. Located in a private neighborhood with dead end streets, it was quiet and peaceful. Sue the owner was quickly responsive when we had any questions. We are recommending the cottage to our family."
Vintage Waterfront Cottage with Stunning Sunsets
Interior
Waterfront Historical District Home Near River
3.0 star property
Waterfront Historical District Home Near River
Property grounds
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
9.6 out of 10, Exceptional, (5)
"It was as advertised. It was clean and we had everything we needed. It was a very pleasant visit."
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Marina
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
8.0 out of 10, Very Good, (1)
The price is $195
$232 total
includes taxes & fees
May 23 - May 24
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Interior
Family-friendly Cottage, Walk to the Beach!
3.5 star property
Family-friendly Cottage, Walk to the Beach!
Interior
Waterfront Millington Vacation Rental w/ Hot Tub!
3.0 star property
Waterfront Millington Vacation Rental w/ Hot Tub!
Don't see what you're looking for?
See all available properties in Chesapeake City
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.

Other property types in Chesapeake City

Pool
Historic Chesapeake City Stay
8.0 out of 10, Very Good, (1)
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is $120
$241 total
includes taxes & fees
May 23 - May 24
Historic Chesapeake City Stay
Property grounds
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, (2)
"Two of my brothers and an old friend came down to the c&d canal trail for a long weekend and a lot of bicycle riding. This house was right on the trail. A great house with great views. We were also within walking distance of a very good seafood restaurant. It was a perfect weekend. As far as the house it had everything we needed. We wanted for nothing. When we arrived at the house there was chocolates and snacks waiting for us as well as beers and sodas in the fridge with a note to help...
Chesapeake City Overlook: Breathtaking View!
Smart TV
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
9.6 out of 10, Exceptional, (5)
"Our group of 15 gathered here for a long weekend in July to attend a family event in the area. The house was WONDERFUL, STYLISH & SPACIOUS. And Chesapeake City itself was a surprise bonus… several gift shops, a cute ice cream shop, coffee & breakfast cafe, dinner restaurants - all within walking distance! Loved: everything about the house… proximity to the quaint town… plenty of hot water… awesome AC upstairs…Brad the owner answered emails very quickly… *minor* issues: the main floor AC...
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
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.

Chesapeake City Cottages information

Number of reviews
166
Accommodation
22 Cottages
Lowest Price
$195
Highest Price
$295

Frequently asked questions

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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 Center and Cow Pond are worthwhile additions to your itinerary.

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