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Our top choices for Chester cottages

Exterior
The Tiny Cottage at Clem & Clyde's

Cottage in Oakdale,

The Tiny Cottage at Clem & Clyde's
2.0 star property
10.0 out of 10, Exceptional, (1)
"This is a perfect place to get away from the city and feel nostalgic about the memories I had when I lived in a small village. It’s a cozy, warm little cottage—perfect for staying a few days. The setup and furniture in the house have everything we need, even for just a one-night stay. The room is clean and spotless, and very well maintained. The host, Tom, is very friendly and helped introduce us to his animals. We arrived during the first snowfall of the winter season, and the view outside the...
United States
Junlin
$106 nightly
The price is $118
Dec 21 - Dec 22
Total with taxes and fees
The Tiny Cottage at Clem & Clyde's
Exterior
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
$173 nightly
The price is $196
Jan 6 - Jan 7, 2026
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
2.0 star property
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
$259 nightly
The price is $294
Dec 21 - Dec 22
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Terrace/patio
115 Rose Cottage with 2 bedroom walk to Groton Bay

Cottage in Groton

115 Rose Cottage with 2 bedroom walk to Groton Bay
8.8 out of 10, Excellent, (8)
"Very nice little place. Quite, clean and only minutes from Mystic and downtown New London."
United States
Nicholas C.
$289 nightly
The price is $327
Dec 21 - Dec 22
Total with taxes and fees
115 Rose Cottage with 2 bedroom walk to Groton Bay
Exterior
Beach Cottage, private beach and pass

Cottage in East Lyme

Beach Cottage, private beach and pass
10.0 out of 10, Exceptional, (9)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
$421 nightly
The price is $476
Jan 14 - Jan 15, 2026
Total with taxes and fees
Beach Cottage, private beach and pass
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

Clarion Inn

10/10 Excellent
"Very clean and well kept "
Brian 3-night trip
Posted 2 days ago
Clarion Inn

Find out more about Chester

Chester Cottages information

Number of reviews
31
Accommodation
133 Cottages
Lowest Price
$118
Highest Price
$476

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between $118 and $476 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 133 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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