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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chester cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

1. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is NZ$398
includes taxes & fees
20 Oct - 21 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A white cottage with a front door, a garage, and a small porch with a potted plant.

2. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is NZ$550
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, multiple windows, and a front door.

3. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Great host and property"
United States
Kevin K.
The price is NZ$904
includes taxes & fees
23 Sept - 24 Sept
Adorable Cottage with Cottage porch, walk to water & town
A two-story house with a porch, a mailbox, and a lawn.

4. 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
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is NZ$606
includes taxes & fees
28 Sept - 29 Sept
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A small white house with black shutters, a porch, and a red barn in the background.

5. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is NZ$258
includes taxes & fees
28 Sept - 29 Sept
The Tiny Cottage & Mini Farm
A compact kitchen with white cabinets, a microwave, an oven, a refrigerator, and a trash bin.

6. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
8.0 out of 10, Very good, (2 reviews)
"We enjoyed our stay at the cottage. It was perfect for traveling with our dogs very comfortable, nice and quiet."
United States
Ed B.
The price is NZ$599
includes taxes & fees
29 Sept - 30 Sept
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A small, single-story house with a white porch and a wooden front door.

7. 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, (33 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is NZ$685
includes taxes & fees
21 Oct - 22 Oct
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
A coastal residential area with houses, a beach, and a pier.

8. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (96 reviews)
"Great cottage on the Sound!"
United States
David S.
The price is NZ$1,977
includes taxes & fees
28 Sept - 29 Sept
Direct waterfront renovated cottage.
A wooden house with a porch, stone steps, and a gravel pathway.

9. Large Family-Friendly Cottage

Large Family-Friendly Cottage
Waterford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our weekend at Marina Bay for our daughter’s birthday weekend with her friends. Everything was easy to find and use, the space was perfectly sized and comfortable. We hope to return soon!"
United States
Henry B.
Large Family-Friendly 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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Beautiful property.The staff were very accommodating ,helpful and friendly.The only complaint to report was the lack of on site eating facilities .We arrived on a rainy Sunday and the outside venue for lunch was closed.The bar did not serve food until 3:30.The only option was the Sunday buffet which was priced at $59.00pp.Starbucks was limited to a grilled cheese or a ham egg sandwich.We were forced to leave the property to have lunch . The espresso martini was priced at &20.00 a tad high .Overall it was an enjoyable stay."
Mary 1-night trip
Posted 5 hours ago
Water's Edge Resort & Spa

Find out more about Chester

Chester Cottages information

Number of reviews
241
Accommodation
136 Cottages
Lowest Price
NZ$258
Highest Price
NZ$1,977

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between NZ$258 and NZ$1,977 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 136 cottages located in Chester. To help you find your ideal place, use our handy filter tool to search for must-have amenities.
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 Theatre. It's a winner with locals and tourists alike.

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