A calm river with boats, wooden docks, and buildings along the shore.

Search Chester Cottage Rentals from CA $323

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Our top choices for Chester cottages

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $234
CA $410 total
includes taxes & fees
Jul 19 - Jul 20
1-bedroom cottage with Grove Beach 🏖️ access.

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (156 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
The price is CA $291
CA $550 total
includes taxes & fees
Jul 26 - Jul 27
Go Jump in the Lake!

The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (9 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is CA $224
CA $323 total
includes taxes & fees
Jul 12 - Jul 13
The Tiny Cottage & Mini Farm

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (17 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is CA $224
CA $517 total
includes taxes & fees
Jul 12 - Jul 13
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
The price is CA $567
CA $1,006 total
includes taxes & fees
Jul 15 - Jul 16
Beach Cottage, private beach and pass

Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
The price is CA $277
CA $496 total
includes taxes & fees
Jul 20 - Jul 21
Privet Farm cottage with AC and Deck in charming Salem Connecticut

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (28 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is CA $491
CA $819 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (49 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is CA $685
CA $1,161 total
includes taxes & fees
Jul 12 - Jul 13
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
The price is CA $459
CA $869 total
includes taxes & fees
Aug 1 - Aug 2
Adorable Cottage with Cottage porch, walk to water & town

Private Two-Bedroom Cottage

Private Two-Bedroom Cottage
Waterford
6.0 out of 10, (1 review)
The price is CA $429
CA $490 total
includes taxes & fees
Jul 26 - Jul 27
Private Two-Bedroom Cottage
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

Find out more about Chester

Chester Cottages information

Number of reviews
325
Accommodation
141 Cottages
Lowest Price
CA $323
Highest Price
CA $1,161

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between CA $323 and CA $1,161 per night for cottages in Chester. No matter your budget, an epic stay is only a click or two away on Expedia. 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.
How many cottages are there in Chester?
Enjoy reconnecting with nature in one of the 141 cottages located in Chester. To help you find your ideal place, use our handy filter tool to search for must-have amenities.
Why book your cottage in Chester with Expedia?
We think that a vacay should be simple, so if you're after cottages in Chester at a great price, Expedia delivers. Stick to the budget and go for a wallet-friendly option far from the hustle and bustle, or book a luxury cottage to spoil your favorite people.
How can I find cheap cottages in Chester?
With Expedia's filter tool, scoring cheap cottages in Chester has never been simpler. To view properties that'll make your bank balance smile, refine your search by amenities, budget and star rating.
What is there to do in Chester near my cottage?
If you're eager to discover the best of Chester, find your way to Norma Terris Theater. It's a winner with locals and tourists alike.

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