Photo by Patricia Knorr

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Chester cottages

Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is AED 470
AED 1,016 total
includes taxes & fees
25 Dec - 26 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is AED 1,465
AED 3,251 total
includes taxes & fees
13 Dec - 14 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
11 Dec - 12 Dec
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
The price is AED 1,179
AED 2,119 total
includes taxes & fees
5 Jan - 6 January 2026
Secluded Cozy Cottage in Historic Downtown
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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Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

How much do cottages in Chester cost?
Rates for cottages in Chester range between AED 1,016 and AED 3,251 per night. No matter your budget, you'll find the ideal place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chester with Expedia?
We think that vacays should be a piece of cake, so if you're in search of cottages in Chester at a great price, Expedia is here to help. Keep the budget in check and go for a wallet-friendly option far from the hustle and bustle, or book a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Chester?
With Expedia's handy filter tool, getting your hands on cheap cottages in Chester is easy. To view properties that are very pocket friendly, refine your search results by star rating, amenities and budget.