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Our top choices for Chester cottages

The Tiny Cottage on The Pond

The Tiny Cottage on The Pond
Oakdale,
10.0 out of 10, Exceptional, (8 reviews)
"Host was extremely nice and responsive. Cottage is so cute I can't wait to come back in the summer! Nice and private little place and adorable goats! If you're looking for a quiet, cute little getaway this is the place to go! Thank you Thomas for the hospitality!!"
United States
Sharon O.
$186 nightly
The price is $210
Jun 15 - Jun 16
Total with taxes and fees
The Tiny Cottage on The Pond

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (42 reviews)
"Extremely cozy, comfortable and clean! Really impressed after walking through the door...details of flowers, fruit, water, and coffee and tea. Pleasantly Surprised and would definitely stay again and recommend. Thank you!!"
United States
Kristen B.
$208 nightly
The price is $236
May 18 - May 19
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

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.
$414 nightly
The price is $468
May 18 - May 19
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town

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, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$275 nightly
The price is $312
Jun 4 - Jun 5
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

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, (22 reviews)
"The home was exactly as described and well appointed, yet charming and cozy. Great location near Niantic, Stonington and Mystic. Perfect for a sister’s birthday getaway. "
United States
Dianne B.
$314 nightly
The price is $355
May 19 - May 20
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
$581 nightly
The price is $657
May 27 - May 28
Total with taxes and fees
Beach Cottage, private beach and pass

Private One-Bedroom Cottage

Private One-Bedroom Cottage
Waterford
$452 nightly
The price is $452
Jun 12 - Jun 13
Total with taxes and fees
Private One-Bedroom Cottage

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
$667 nightly
The price is $755
May 18 - May 19
Total with taxes and fees
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

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, (44 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
$527 nightly
The price is $597
May 18 - May 19
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
NEW Coastal Cottage 2 Miles to Beach + Lake Access
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
151
Accommodation
140 Cottages
Lowest Price
$210
Highest Price
$755

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between $210 and $755 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 140 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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