Search Chester Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Chester cottages

Exterior

The Tiny Cottage on The Ranch

The Tiny Cottage on The Ranch
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.
$133 nightly
The price is $149
May 6 - May 7
Total with taxes and fees
The Tiny Cottage on The Ranch
Exterior

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (41 reviews)
"We had such a wonderful one night stay at Shalom Cottage! The place was absolutely beautiful—so cozy, clean, and thoughtfully decorated. Raj, the host was truly amazing! He was kind, responsive, and made sure we had everything we needed from start to finish. We felt so welcomed and comfortable the entire time. We would definitely love to stay here again and highly recommend it to anyone! "
United States
Alexis F.
$197 nightly
The price is $223
May 14 - May 15
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

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.
$309 nightly
The price is $350
May 13 - May 14
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Exterior

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.
$576 nightly
The price is $652
May 14 - May 15
Total with taxes and fees
Beach Cottage, private beach and pass
Smart TV, foosball, table tennis

Private One-Bedroom Cottage

Private One-Bedroom Cottage
Waterford
$339 nightly
The price is $339
May 15 - May 16
Total with taxes and fees
Private One-Bedroom Cottage
Exterior

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.
$213 nightly
The price is $242
May 11 - May 12
Total with taxes and fees
NEW Coastal Cottage 2 Miles to Beach + Lake Access
Exterior

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.
$502 nightly
The price is $571
May 11 - May 12
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Exterior

East Haddam Lake View Rental

East Haddam Lake View Rental
East Haddam
$429 nightly
The price is $494
May 26 - May 27
Total with taxes and fees
East Haddam Lake View Rental
Property grounds

Studio Cottage at Marina Bay

Studio Cottage at Marina Bay
Waterford
$286 nightly
The price is $286
May 15 - May 16
Total with taxes and fees
Studio Cottage at Marina Bay
Exterior detail

Private Two-Bedroom Cottage

Private Two-Bedroom Cottage
Waterford
6.0 out of 10, (1 review)
$434 nightly
The price is $434
May 15 - May 16
Total with taxes and fees
Private Two-Bedroom Cottage
Smart TV, foosball, table tennis

Private Cottage at Marina Bay

Private Cottage at Marina Bay
Waterford
10.0 out of 10, Exceptional, (1 review)
"Place was very clean and cozy. Very close to the area fishing charters. Highly recommend. "
United States
Danielle R.
$365 nightly
The price is $365
May 15 - May 16
Total with taxes and fees
Private Cottage at Marina Bay
Smart TV, foosball, table tennis

Sun-Filled Private Large Cottage

Sun-Filled Private Large Cottage
Waterford
$529 nightly
The price is $529
May 15 - May 16
Total with taxes and fees
Sun-Filled Private Large 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Days Inn by Wyndham Berlin Meriden

Days Inn by Wyndham Berlin Meriden

2/10 Terrible
"The staff is awful so it really doesn’t matter if the amenities are good or not we were thrown out and didn’t get our money back because they happen to be a girl there. It was speaking to us and was apparently on the no stay list. Outrageous."
Darren 1-night trip
Posted 8 hours ago
Days Inn by Wyndham Berlin Meriden

Find out more about Chester

Chester Cottages information

Number of reviews
129
Accommodation
140 Cottages
Lowest Price
$149
Highest Price
$652

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between $149 and $652 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.

Explore a world of travel with Expedia