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

Search Chester Cottage Rentals from CA $675

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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

House (3 Bedrooms) | Interior

1. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is CA $311
CA $675 total
includes taxes & fees
Oct 8 - Oct 9
Idyllic Pasadena Retreat With Garden + Hot Tub!
Outdoor dining

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.
The price is CA $500
CA $924 total
includes taxes & fees
Sep 17 - Sep 18
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina

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.
The price is CA $750
CA $1,185 total
includes taxes & fees
Sep 21 - Sep 22
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

10/10 Excellent
"Every thing was amazing. The staff was extremely helpful and the parking situation was perfect. Room was top notch."
Jennifer 4-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
CA $675
Highest Price
CA $1,185

Frequently asked questions

How much do cottages in Chester cost?
Rates for cottages in Chester range between CA $675 and CA $1,185 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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