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Apartments
Apartments
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Cottages
Cottages

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 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
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
The price is NZ$403
includes taxes & fees
10 Nov - 11 Nov
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, (31 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is NZ$605
includes taxes & fees
7 Nov - 8 Nov
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, a mailbox, and a lawn.

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
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is NZ$496
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

4. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is NZ$672
includes taxes & fees
17 Nov - 18 Nov
Westbrook Getaway-Near Beaches, Train & Shoreline
A two-story house with a porch, multiple windows, and a front door.

5. 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)
"Very clean and comfortable"
United States
Francine F.
The price is NZ$972
includes taxes & fees
8 Nov - 9 Nov
Adorable Cottage with Cottage porch, walk to water & town
A small white house with black shutters, a porch, and a red barn in the background.

6. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (14 reviews)
"Love love love this place. A very unique setting on a little farm and the cabin was great. Everything ya need. A gorgeous setting. Tom, the owner is great. Will. Be. Back."
United States
Paul
The price is NZ$297
includes taxes & fees
15 Nov - 16 Nov
The Tiny Cottage & Mini Farm
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, (36 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is NZ$561
includes taxes & fees
8 Nov - 9 Nov
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

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

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
9.0 out of 10, Wonderful, (4 reviews)
"The place was perfect! So much bigger and nicer in person!!!!! Well appointed very cozy! Clean!!!!! Very pet friendly! Great shower!"
United States
Kellie
The price is NZ$528
includes taxes & fees
9 Nov - 10 Nov
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A small white house with a green door, two wicker chairs with red cushions, and a welcome mat.

9. 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, (9 reviews)
"We had a great time and the property provided everything we needed. Thank you!"
United States
Meredith
The price is NZ$694
includes taxes & fees
7 Dec - 8 Dec
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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Learn more about Chester

Charming galleries and local shops line Main Street, where you'll find handcrafted jewellery and Connecticut River Valley artwork. Catch a performance at the Goodspeed Opera House in East Haddam or kayak Chester Creek when summer temperatures rise.

See all hotels in Chester
A calm lake surrounded by vibrant autumn foliage.

Frequently Asked Questions

How much do cottages in Chester cost?

You can expect to pay between NZ$297 and NZ$972 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 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.