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Cottages in Chester

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

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

2.0 star property
North Beach
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
$261 nightly
The price is $277
Nov 22 - Nov 23
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Exterior
#2 Egret Cottage Harris Cove

#2 Egret Cottage Harris Cove

Saint Michaels
10.0 out of 10, Exceptional, (1)
$355 nightly
The price is $384
Nov 26 - Nov 27
Total with taxes and fees
#2 Egret Cottage Harris Cove
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$792 nightly
The price is $874
Dec 1 - Dec 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Nov 24 - Nov 25
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Historic District
9.6 out of 10, Exceptional, (15)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
$657 nightly
The price is $749
Nov 24 - Nov 25
Total with taxes and fees
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
"Everything was great"
Warren 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Chester

Chester Cottages information

Number of reviews
16
Accommodation
84 Cottages
Lowest Price
$277
Highest Price
$874

Frequently asked questions

How much do cottages in Chester cost?
Rates for cottages in Chester range between $277 and $874 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.

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