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.
Super 8 by Wyndham Old Saybrook
Price was CA $816, price is now CA $737 per person
CA $737
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (925 reviews)
The office was not open when we got there had to keep ringing the buzzer when we left in the morning there was no one in the office.
Reviewed on Jun 14, 2026
Quality Inn Old Saybrook - Westbrook
Price was CA $911, price is now CA $911 per person
CA $911
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.8/10 Good! (1,010 reviews)
The room was very clean and quiet. The interior was modern and very well laid out. The breakfast was very good.
Reviewed on Jun 8, 2026
Chester Hotel Deals
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
The price is CA $101 per night from Jun 28 to Jun 29
CA $101
CA $117 total
Jun 28 - Jun 29
includes taxes & fees
7.2/10 Good! (1,008 reviews)
"It was an ok place just to stay one night to catch a flight in the morning. Beds were not comfortable, I could feel springs poking into my back. The room appeared to be clean."
Reviewed on Jun 22, 2026
Regency Inn & Suites New London, Mystic
269 North Frontage Road New London CT
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Jun 25 to Jun 26
CA $137
CA $157 total
Jun 25 - Jun 26
includes taxes & fees
6/10 (1,008 reviews)
"Nice clean hotel only downside is no elevator."
Reviewed on Jun 23, 2026
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Jul 7 to Jul 8
CA $139
CA $159 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (2,703 reviews)
"Rooms were clean but very outdated. Some of the elevators had a terrible smell. Food on the floor in hallway outside my room Staff was pleasant when checked in."
Reviewed on Jun 23, 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.
