A boat docked at a pier during twilight with a city skyline in the background.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chester cottages

A covered patio with a wicker sofa, a glass coffee table, a wooden table, and a bench.

1. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$426 nightly
The price is $485
Oct 8 - Oct 9
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!
A wooden deck with wicker furniture, a round table, and a fire pit.

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Sep 17 - Sep 18
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A marina with multiple sailboats docked.

3. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
$760 nightly
The price is $866
Sep 20 - Sep 21
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Very impressed with the staff and all the help they provided for us.....! Cleanliness tops. My only complaint is with the cable TV quality. Very poor picture quality and cumbersome remote. This certainly requires a big upgrade. Also it wasn`t till the second day that I found electric outlets for charging phones , etc , on the face of the bedside stands and table If you outline the outlets with a narrow line of white tape, they would be easily noticed , The outlets were dark and against the dark wood of the furniture in low lit rooms was almost impossible to see. Small peanuts, but a easy upgrade. We enjoyed our stay !!! Thanks"
Pamela 2-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Find out more about Chester

Chester Cottages information

Number of reviews
22
Accommodation
92 Cottages
Lowest Price
$485
Highest Price
$866

Frequently asked questions

How much do cottages in Chester cost?
Rates for cottages in Chester range between $485 and $866 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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