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.
Liberty Inn
Price was CA $686, price is now CA $645 per person
CA $645
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7.6/10 Good! (645 reviews)
I'll start off with the positives:
- The greeter, who I presume was the owner, was kind and allowed me to start my check-in early (with a fee, but that was to be expected).
- The property, despite having the layout of a motel, looked very nice. And the moment I stepped into my room, it felt I was in a high-class hotel.
- Most (not all, but I'll get to that in the negatives) amenities were provided.
- The price, compared to what else I was finding in the area, was relatively inexpensive.
And now for the negatives:
- A very minor one, but tissues would be a nice amenity to have had in the room.
- The location is close to the highway. Probably great for finding business from weary travelers, but unideal for morning-sleepers like I.
- The chairs in the room, though looking nice, felt cheaply made. I heard the one I sat at cracking as I sat, and I feared it might break underneath me.
Reviewed on Apr 27, 2026
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $908, price is now CA $739 per person
CA $739
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
Parking was easy. Bed mattress terrible. Tired room and furnishings. Basic supplies.
Reviewed on Apr 28, 2026
Madison Beach Hotel
Madison Center
Price was CA $2,065, price is now CA $1,776 per person
CA $1,776
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.4/10 Exceptional! (367 reviews)
Excellent hotel, high quality in every way, beautiful setting, very quiet relaxing and peaceful Sunday night stay off-season.
Reviewed on Apr 28, 2026
Tower Inn And Suites Of Guilford - Madison
Price was CA $805, price is now CA $792 per person
CA $792
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7.4/10 Good! (243 reviews)
It was great. Easy check in and check out. Love that the chexk out qas at 11 and noe wicked early. If i go to a event in the area again i would definitely stay here again.
Reviewed on May 4, 2026
Chester Hotel Deals
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jun 1 to Jun 2
CA $157
CA $181 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (2,689 reviews)
There was a shuttle to and from Mohegan which was awesome. The breakfast was a nice touch. The staff were….interesting. Pleasant enough but belching and other unpleasant behaviors.
Reviewed on May 8, 2026
Mohegan Sun
1 Mohegan Sun Boulevard Montville CT
9.2/10 Wonderful! (2,008 reviews)
Housekeeping did not come to clean the room until 5pm
Reviewed on May 4, 2026
Red Roof Inn Meriden
10 Bee St Meriden CT
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from May 10 to May 11
CA $122
CA $140 total
May 10 - May 11
includes taxes & fees
7.4/10 Good! (1,003 reviews)
I had a really great stay at this Red Roof Inn. The room was super clean, which is my number one priority, so that was a big win. Everything felt comfortable and well kept. The staff was friendly and made everything easy, and there was plenty of parking, which was a huge plus. The location is also ...
Reviewed on May 2, 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.
