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Compare 28 Cottages in Chesapeake City with updated reviews, rates, and availability.

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (60)
"What an amazing and cozy little cottage with awesome views of the Delaware river. Beth was wonderful and thought of everything! From the comfortable beds to the fine linens and bedding, Beth had it covered. The home is well appointed, very clean, and located towards the end of a quiet and peaceful dead-end street. Our three dogs felt right at home; we were thrilled to find such a quaint place that allowed us to bring them along. We highly recommend Beth’s cottage and we would definitely book...
A cottage on the shore of the Delaware River

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

9.8 out of 10, Exceptional, (6)
"Only there overnight. "
The price is SAR 731
SAR 867 total
includes taxes & fees
1 Apr - 2 Apr
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (45)
"Great little home away from home. A small orientation list for newcomers would be helpful. Closest groceries, gas and such. Outside of that all and all VERY pleasing. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa

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

9.8 out of 10, Exceptional, (7)
"On a small hillside. Very quaint accommodation. Close to restaurants and river. Parking a little difficult to figure out, train is a bit loud and frequent but everything else was as advertised and nice. "
The price is SAR 555
SAR 847 total
includes taxes & fees
7 Apr - 8 Apr
Quarry Landing - Center of Town & River View - 3 Bedroom

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

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (11)
"This is a very clean, beautiful home on the inside and out. They have everything you need! Raymond was an EXCELLENT host who was super responsive and understanding. I highly recommend. You will not be disappointed. Thank you, Raymond! We can't wait to come back! "
The price is SAR 933
SAR 2,028 total
includes taxes & fees
1 Apr - 2 Apr
Thunder Hill Retreat - Spacious/Deck/Hot tub

Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay

2.0 star property
9.0 out of 10, Wonderful, (2)
"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 - Waterfront Boho Cottage on the Elk River /Chesapeake Bay

Waterfront cottage in historic Charlestown, Maryland

9.6 out of 10, Exceptional, (5)
"Our stay was amazing! Extremely cute and clean cottage. Water view was beautiful. Very relaxing weekend. Great communication with host. Can’t wait to go back. "
Waterfront cottage in historic Charlestown, Maryland

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

Private Carriage House Retreat on a 33 Acre Historic Working Estate

10.0 out of 10, Exceptional, (11)
"Place was great !"
Private Carriage House Retreat on a 33 Acre Historic Working Estate

Charming 2-bedroom water oriented cottage with water access

Charming 2-bedroom water oriented cottage with water access

Vintage Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (5)
"thoroughly enjoyed our time at this lovely property. the quiet location, attention to detail, and communication with owners all made for an delightful stay. "
Vintage Waterfront Cottage with Stunning Sunsets

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very Good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"We had a wonderful time! Being near the water is my happy place. The size of the home is perfect for me. And the weather was perfect! Thank you!"
The price is SAR 1,218
SAR 1,909 total
includes taxes & fees
6 Apr - 7 Apr
Long Beach Cottage, (romantic couple’s getaway)

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!

Waterfront Historical District Home Near River

3.0 star property
10.0 out of 10, Exceptional, (1)
"The home was beautiful and well kept. Essential kitchen items are included along with sheets and towels. Dawn was a super reliable host. Communication was wonderful. She had toiletries and some stocked snacks for the guests. Although we did not have time to use them, there were cornhole 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. I would recommend this house to anyone looking for...
Waterfront Historical District Home Near River

3 Mi to Dtwn: Home w/ Yard in Newark

3.0 star property
3 Mi to Dtwn: Home w/ Yard in Newark

Waterfront Millington Vacation Rental w/ Hot Tub!

3.0 star property
Waterfront Millington Vacation Rental w/ Hot Tub!

Spacious North East Home w/ Fenced Yard & Fire Pit

3.0 star property
Spacious North East Home w/ Fenced Yard & Fire Pit
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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Other property types in Chesapeake City

Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was an abundant blessing. The hot tub was just the added bonus for those chilly winter evenings. Communication with Jon was superb and his kindness and consideration go above and beyond a 5 Star review!!! Thanks for allowing our family an awesome Christmas!! We can’t wait to be back!!"
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is SAR 450
SAR 1,093 total
includes taxes & fees
1 Apr - 2 Apr
Historic Chesapeake City Stay

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (52)
"We had an unforgettable stay at this property! The house and two bungalows exceeded all expectations. The entertainment/living room is massive—one of the largest I’ve ever seen—and offers incredible views of the river from almost every angle. Watching the sunrise and sunset through the large windows was absolutely breathtaking. The kitchen was impressively well-stocked, making meal prep a breeze. There are two dining areas: one table that seats ten and another that seats six, offering...
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
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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