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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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

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, (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.
Smart TV, books

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

9.8 out of 10, Exceptional, (8)
"Private, quiet cottage, clean and easy check-in / check-out."
The price is AED 716
AED 837 total
includes taxes & fees
17 Apr - 18 Apr
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (46)
"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
Hill Top Cottage with Chickens!
Property grounds

Hill Top Cottage with Chickens!

10.0 out of 10, Exceptional, (7)
"We loved it and would recommend to anyone looking for a quick getaway."
Hill Top Cottage with Chickens!
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

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
Property grounds

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 AED 544
AED 829 total
includes taxes & fees
22 Apr - 23 Apr
Quarry Landing - Center of Town & River View - 3 Bedroom
Chesapeake Romantic Waterfront Home with Private Pool
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
Thunder Hill Retreat - Spacious/Deck/Hot tub
Outdoor spa tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (12)
"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 AED 1,079
AED 2,189 total
includes taxes & fees
9 Apr - 10 Apr
Thunder Hill Retreat - Spacious/Deck/Hot tub
Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay
Terrace/patio

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
Interior

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
Marina

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
Exterior

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
Fridge, microwave, oven, stovetop

Charming 2-bedroom water oriented cottage with water access

Charming 2-bedroom water oriented cottage with water access
Vintage Waterfront Cottage with Stunning Sunsets
Beach nearby, sun loungers, beach towels

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!
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!
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

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 AED 1,317
AED 2,005 total
includes taxes & fees
8 May - 9 May
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)
"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
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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
Interior

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!
House (Multiple Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Waterfront Millington Vacation Rental w/ Hot Tub!

3.0 star property
Waterfront Millington Vacation Rental w/ Hot Tub!
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 City Quiet Overlook
Outdoor dining

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "
Chesapeake City Quiet Overlook
Historic Chesapeake City Stay
Pool

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AED 441
AED 1,055 total
includes taxes & fees
18 Apr - 19 Apr
Historic Chesapeake City Stay
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exterior

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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