Chester Vacation Packages
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Your Chester Vacation
The best way to experience this vibrant city is with a custom-made Chester vacation package. Stay in the neighborhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. Essex Steam Train, Goodspeed Opera House and Essex Island Marina are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect vacation to Chester now.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $1,061, price is now CA $837 per person
CA $837
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Comfortable for a nights stay. Close to nice restaurants and shopping.
Reviewed on May 21, 2026
Chester Hotel Deals
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
The price is CA $159 per night from Jun 15 to Jun 16
CA $159
CA $183 total
Jun 15 - Jun 16
includes taxes & fees
9.2/10 Wonderful! (2,691 reviews)
"Booked a double queen room and when I arrived and checked in the reception was good. Got to my room to walk into a King bed. I was with my 14 year old granddaughter for a volleyball tournament. I was Told they did not have any double queen rooms available. Why bother booking a double queen room if ..."
Reviewed on May 24, 2026
Mohegan Sun
1 Mohegan Sun Boulevard Montville CT
9.2/10 Wonderful! (1,973 reviews)
"Very nice, clean place"
Reviewed on May 22, 2026
Red Roof Inn Meriden
10 Bee St Meriden CT
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from May 26 to May 27
CA $131
CA $150 total
May 26 - May 27
includes taxes & fees
7.4/10 Good! (1,004 reviews)
"staffs are helpful"
Reviewed on May 22, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
