Chester Vacation Packages
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- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
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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.
Quality Suites Stratford
Price was CA $553, price is now CA $551 per person
CA $551
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8/10 Very Good! (1,000 reviews)
In the middle of a neighborhood so no close restaurants or amenities
Reviewed on Mar 16, 2026
Chester Hotel Deals
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Mar 31 to Apr 1
CA $135
CA $155 total
Mar 31 - Apr 1
includes taxes & fees
9.2/10 Wonderful! (2,674 reviews)
Room was great.
Reviewed on Mar 23, 2026
Mohegan Sun
1 Mohegan Sun Boulevard Montville CT
9.2/10 Wonderful! (2,045 reviews)
Extremely clean rooms
Reviewed on Mar 24, 2026
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
The price is CA $90 per night from Mar 29 to Mar 30
CA $90
CA $105 total
Mar 29 - Mar 30
includes taxes & fees
7.2/10 Good! (1,003 reviews)
You get why you pay for. We just needed a cheap stay for one night. The toilet seat was loose and falling off. The hallway smells like straight up cigarette smoke, and floors were a bit dirty. Pillows were super small (one per head basically). We didnt use the shower but I did look inside and the ...
Reviewed on Mar 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.
