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

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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chester cottages

Exterior

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 443
AED 850 total
includes taxes & fees
6 Oct - 7 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

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)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is AED 643
AED 1,174 total
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

3. 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, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is AED 579
AED 1,333 total
includes taxes & fees
20 Sep - 21 Sep
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Exterior

4. 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 AED 422
AED 559 total
includes taxes & fees
6 Oct - 7 Oct
The Tiny Cottage & Mini Farm
Private kitchen

5. 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 AED 645
AED 1,190 total
includes taxes & fees
10 Sep - 11 Sep
Privet Farm cottage with AC and Deck in charming Salem Connecticut
Exterior

6. 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 home is very well kept and is in a wonderful location. We enjoyed it a great deal and would go back in a heart beat."
United States
Chrissy R.
The price is AED 830
AED 1,542 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Smart TV, foosball, table tennis

7. Private One-Bedroom Cottage

Private One-Bedroom Cottage
Waterford
Private One-Bedroom Cottage
Terrace/patio

8. 115 Rose Cottage with 2 bedroom walk to Groton Bay

115 Rose Cottage with 2 bedroom walk to Groton Bay
Groton
8.8 out of 10, Excellent, (8 reviews)
"Very nice little place. Quite, clean and only minutes from Mystic and downtown New London."
United States
Nicholas C.
The price is AED 735
AED 1,662 total
includes taxes & fees
5 Oct - 6 Oct
115 Rose Cottage with 2 bedroom walk to Groton Bay
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

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

10/10 Excellent
"Tavern was nice with food . Under renovation so not as clean building supplies everywhere"
Carol 2-night trip
Posted 12 hours ago
Clarion Inn North Haven - New Haven North

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between AED 559 and AED 1,662 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.
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.