Search Cottages in Chesapeake City

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Compare 23 Cottages in Chesapeake City with updated reviews, rates, and availability.

A cottage on the shore of the Delaware River
Exterior detail
A cottage on the shore of the Delaware River
9.8 out of 10, Exceptional, (59)
"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "
A cottage on the shore of the Delaware River
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
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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
Quarry Landing - Center of Town & River View - 3 Bedroom
Room
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 556
SAR 876 total
includes taxes & fees
3 Dec - 4 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom
Family-Friendly Cottage, Walk to the Beach!
Kennedyville Vacation Rental | 2BR | 1BA | 4 Stairs to Access | 1,000 Sq Ft
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!
Thunder Hill Retreat - Peaceful - sleeps 12
Thunder Hill Retreat - Peaceful - sleeps 12
10.0 out of 10, Exceptional, (9)
"In the area to move our daughter in to her sophomore year of college"
The price is SAR 710
SAR 1,765 total
includes taxes & fees
24 Nov - 25 Nov
Thunder Hill Retreat - Peaceful - sleeps 12
Chesapeake Romantic Waterfront Home with Private Pool
Pool closed in winter and virtually staged because it was closed during pic.
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
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.
Exterior
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.
8.8 out of 10, Excellent, (3)
"Enjoyed our stay. House was perfect for the 2 of us. Definitely better than staying in a noisy hotel!"
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.
Hill Top Cottage with Chickens!
Living area
Hill Top Cottage with Chickens!
10.0 out of 10, Exceptional, (5)
"My husband and I were going to be in town for an event and didn’t want to stay in a hotel room. We were able to have a house all to ourselves that was cozy, quiet, and clean. The beds were comfortable, and we loved the electric fireplace. With the owner was excellent! "
Hill Top Cottage with Chickens!
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!
Waterfront cottage in historic Charlestown, Maryland
Aerial view
Waterfront cottage in historic Charlestown, Maryland
9.6 out of 10, Exceptional, (4)
"It was hot the week we stayed, and the ac could not keep up. and the creek was too low to kayak to the bay. It was a short walk to the beach which was nice. All and all it was a nice stay. "
Waterfront cottage in historic Charlestown, Maryland
Vintage Waterfront Cottage with Stunning Sunsets
Beach
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 Historical District Home Near River
Living area
Waterfront Historical District Home Near River
3.0 star property
Waterfront Historical District Home Near River
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Front view of the cottage
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
Long Beach Cottage, (romantic couple’s getaway)
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 979
SAR 1,586 total
includes taxes & fees
25 Nov - 26 Nov
Long Beach Cottage, (romantic couple’s getaway)
Charming 2-bedroom water oriented cottage with water access
Exterior
Charming 2-bedroom water oriented cottage with water access
Charming 2-bedroom water oriented cottage with water access
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
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.
9.4 out of 10, Exceptional, (3)
"Very clean, cozy, rustic, safe and remote place to stay. Perfect place to relax but close enough to explore the area. Would definitely go back. Highly recommend it."
The price is SAR 732
SAR 872 total
includes taxes & fees
20 Dec - 21 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Family-friendly Cottage, Walk to the Beach!
Living area
Family-friendly Cottage, Walk to the Beach!
3.0 star property
Family-friendly Cottage, Walk to the Beach!
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

Historic Chesapeake City Stay
Property grounds
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 1,126
SAR 1,922 total
includes taxes & fees
23 Nov - 24 Nov
Historic Chesapeake City Stay
Chesapeake City Quiet Overlook
Backyard looking from Ben Cardin trail and the C&D Canal
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Miscellaneous
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
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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