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Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 29 Cottages in Chesapeake City with updated reviews, rates, and availability.

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
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.

10.0 out of 10, Exceptional, (14)
"Was a charming place to stay close to everything"
The price is SAR 731
SAR 859 total
includes taxes & fees
5 Jun - 6 Jun
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, (47)
"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
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, (61)
"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
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (1)
"Can’t say enough about how nice this place is. We had quick friendly responses from owners. Very clean and the water front view was excellent. Highly recommended "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
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
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!
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!
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)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
The price is SAR 731
SAR 1,058 total
includes taxes & fees
10 Jun - 11 Jun
Quarry Landing - Center of Town & River View - 3 Bedroom
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)
"Thanks Gwendolyn… we had a great time!"
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
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)
"Had a lovely peaceful stay. Great amenities."
Be persuaded to experience this vintage cottage by the Sassa
Thunder Hill Retreat - Spacious/Deck/Hot tub
Outdoor spa tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (12)
"Had a nice stay."
The price is SAR 941
SAR 2,025 total
includes taxes & fees
3 Jun - 4 Jun
Thunder Hill Retreat - Spacious/Deck/Hot tub
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
Hill Top Cottage with Chickens!
Property grounds

Hill Top Cottage with Chickens!

10.0 out of 10, Exceptional, (9)
"The cottage was spotless and had everything we needed to enjoy our stay. The fresh eggs were an unexpected nice touch, and the chickens were quiet and friendly. We plan to return."
Hill Top Cottage with Chickens!
Waterfront cottage in historic Charlestown, Maryland
Interior

Waterfront cottage in historic Charlestown, Maryland

9.6 out of 10, Exceptional, (5)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
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
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"Loved the property and the decor. Very well done and luxurious!"
The price is SAR 1,218
SAR 1,869 total
includes taxes & fees
3 Jun - 4 Jun
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)
"Great location "
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
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio

Grandma’s Cottage will wrap around you like a warm hug

The price is SAR 675
SAR 1,380 total
includes taxes & fees
30 May - 31 May
Grandma’s Cottage will wrap around you like a warm hug
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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