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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 25 Cottages in Chesapeake City with updated reviews, rates, and availability.

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
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
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 AED 544
AED 849 total
includes taxes & fees
10 Feb - 11 Feb
Quarry Landing - Center of Town & River View - 3 Bedroom
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 AED 716
AED 849 total
includes taxes & fees
31 Jan - 1 Feb
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (10)
"In the area to move our daughter in to her sophomore year of college"
The price is AED 734
AED 1,771 total
includes taxes & fees
2 Feb - 3 Feb
Thunder Hill Retreat - Spacious/Deck/Hot tub
Waterfront cottage in historic Charlestown, Maryland
Aerial view

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
Hill Top Cottage with Chickens!
The Living Room

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!
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 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!
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
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
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
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
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
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
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!
Waterfront Historical District Home Near River
Living area

Waterfront Historical District Home Near River

3.0 star property
Waterfront Historical District Home Near River
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 AED 893
AED 1,508 total
includes taxes & fees
3 Feb - 4 Feb
Long Beach Cottage, (romantic couple’s getaway)
3 Mi to Dtwn: Home w/ Yard in Newark
Living area

3 Mi to Dtwn: Home w/ Yard in Newark

3.0 star property
3 Mi to Dtwn: Home w/ Yard in Newark
Spacious North East Home w/ Fenced Yard & Fire Pit
Living area

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 City Quiet Overlook
Backyard looking from Ben Cardin trail and the C&D Canal

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
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 AED 441
AED 1,067 total
includes taxes & fees
1 Mar - 2 Mar
Historic Chesapeake City Stay
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, (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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