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Hotels in Chester

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Chester?

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (94)
  • cleanliness
    Rustic cabin getaway near Machimoodus State Park with patios and kitchenettes.
The price is $119
$183 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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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Budget hotels in Chester and vicinity

Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (463)
The price is $67
$77 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
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 neighborhoods in Chester

Chester Center

The Chester Center neighborhood has lots to see including Norma Terris Theater and Connecticut Valley Railroad State Park Trail.

Top landmarks in Chester

Chester Creek Marina

Imagine strolling along Chester Creek Marina for some great waterfront pics. It's located 2.8 mi (4.5 km) from central Chester.
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Norma Terris Theater

If you want to see a show while you're in town, try and grab some tickets at Norma Terris Theater in Chester Center. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy the show and want to see another, Goodspeed Opera House and Ivoryton Playhouse are both not far.
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Learn more about Chester

Chester is well-known for its attractions such as Connecticut River and Norma Terris Theater.

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Connecticut River Autumn Landscape with the view of landmark architectures on the woodland hill, a tranquil New England scenery

Check out reviews of Chester hotels guests love

Holiday Inn New London - Mystic Area by IHG

Holiday Inn New London - Mystic Area by IHG

10/10 Excellent
"Didn’t have breakfast"
Laurie 1-night trip
Posted 3 days ago
Holiday Inn New London - Mystic Area by IHG

Frequently asked questions

What hotels do travelers like in Chester?
Guests like Water's Edge Resort & Spa and Pier Blue Inn Old Saybrook - Essex.
Can I book refundable accommodations in Chester?
If you need the flexibility to change your plans to Chester, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Chester be like during my vacation?
July and August are typically the warmest months in Chester when the average temp is 70°F. January and February are the coldest months when the average temperature is 35°F. October and December are the months with the most rain.
Why should I book my Chester accommodation with Hotels.com?
There are plenty of reasons to book your Chester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.