Chester, CT

Travel Guide

A calm river with boats, wooden docks, and buildings along the shore.
A calm lake surrounded by vibrant autumn foliage.
A historic waterfront estate with a large white building featuring a balcony and a flagpole.
A marina with boats docked, surrounded by autumn foliage and a cloudy sky.

Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most. Learn more about Chester
Learn more about Chester
A plate of food with three square pieces topped with greens and caviar.
Photo by Annette Babek
Open Photo by Annette Babek

Chester Center

If you're spending some time in Chester Center, Norma Terris Theater and Connecticut Valley Railroad State Park Trail are top sights worth seeing.

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
$99 nightly
The price is $114 total per night from Nov 30 to Dec 1
$114 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Uncasville - Casino Area
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
Book a stay at this luxury resort in Montville. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in ...
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Mohegan Sun
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
$86 nightly
The price is $99 total per night from Dec 1 to Dec 2
$99 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Pier Blue Inn Old Saybrook - Essex
See all 1,109 properties in Chester
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.
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
Stay at this cabin in East Haddam. Enjoy free parking and patios. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

Westbrook CT
Stay at this cottage in Westbrook. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Westbrook Town Beach and Tanger Outlets are located ...
9.4/10 Exceptional! (15 reviews)
"It was cozy"

Reviewed on Sep 3, 2026

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard
Rustic Lakeside Cabin at White Gate Farm

Rustic Lakeside Cabin at White Gate Farm

East Lyme CT
Book a stay at this beach cabin in East Lyme. Enjoy free WiFi, a garden, and patios. Popular attractions White Gate Farm and Cedar Ridge Golf Course are located ...
10/10 Exceptional! (150 reviews)
"We visited to celebrate our tenth anniversary and could not have been more in love with this little, secluded cabin a foot from the water. We enjoyed sitting out by the fire, walking the farm, and kayaking. We will be back!"

Reviewed on Oct 25, 2026

Rustic Lakeside Cabin at White Gate Farm
See all properties in Chester
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.

Stay near popular Chester attractions

Norma Terris Theater

You can enjoy a show at Norma Terris Theater on your trip to Chester. While you're in the area, stroll along the beautiful beaches.
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Frequently asked questions

Is Chester worth visiting?
Chester is worth visiting for its standout attractions, such as the scenic Chester Creek Marina and the cultural experiences at Norma Terris Theater. Travelers can also enjoy a variety of dining options, with local eateries offering Italian and North American cuisine.
When is the best time to visit Chester?
The best time to visit Chester is from May through September, when the weather is typically pleasant for exploring. For fewer crowds and better value, the quieter months of December through March are a good bet. During this cooler period, you can enjoy indoor attractions and cozy experiences without the peak season bustle.
What is a good itinerary length for Chester?
A good itinerary length for Chester is one to two days to see Chester Creek Marina and catch a show at Norma Terris Theater. An extended stay of three to four days allows more time to explore the area and enjoy the Italian, North American, and Asian dining options.
What are the top things to do in and around Chester?
In Chester, travelers can visit the Chester Creek Marina and explore the Norma Terris Theater.
What cuisines can you find in Chester?
In Chester you can find Mexican cuisine, with dishes like tacos, burritos, and enchiladas. You'll also find Italian, North American options like Southern soul food, and Asian dishes including Chinese and Japanese. The destination also offers cafes and a pub scene.
Can I book a refundable hotel in Chester?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chester by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chester with Expedia?
Expedia makes it easier to plan your Chester trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chester?
The best choice depends on your travel style. Hotels in Chester can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chester trip on Expedia?
Once you've booked your Chester trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chester trip?
Expedia offers customer support before, during, and after your Chester trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chester?
If it's your first trip to Chester, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chester hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chester hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chester

A calm river with dense greenery on both sides.

Killingworth

A marina with boats docked, a small white house, and a forested shoreline.

Old Lyme

A forest stream with a small waterfall surrounded by rocks and trees.

Deep River

A white bridge over a river surrounded by autumn-colored trees and hills.

East Haddam

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