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 $722, price is now CA $600 per person
CA $600
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
Room could have been cleaner. The floor was dirty. The room also looked worn and in need of updating. The tub faucet dripped constantly, but the shower was nice. Staff was friendly. I was surprised they don’t offer daily housekeeping. Bed was comfortable. It was great that the room had a microwave and a fridge. It was not warm and inviting at all. Definitely wouldn’t stay more than one night.
Reviewed on Mar 30, 2026
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Price was CA $3,094, price is now CA $2,657 per person
CA $2,657
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.6/10 Exceptional! (64 reviews)
The rooms are spacious and clean, kitchen is fully equipped for those who want to cook.
Reviewed on Mar 29, 2026
Heritage Hotel, Golf & Conference Center
Price was CA $733, price is now CA $648 per person
CA $648
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.4/10 Very Good! (1,008 reviews)
The room was very clean and comfortable. The staff is really great! Our room must have had a lose pipe or vent in the wall behind the shower so it would bang on the wall alot. Once we got used to it it wasnt bad. That is my only complaint. The stay other then that was great!
Reviewed on Mar 31, 2026
Chester Hotel Deals
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Apr 15 to Apr 16
CA $137
CA $157 total
Apr 15 - Apr 16
includes taxes & fees
9.2/10 Wonderful! (2,681 reviews)
I was very surprised at the upkeep off the property and room, it was poor condition. Furniture of the room was not appealing at all, heavily damaged tables, the condition of the bathroom tub was horrible and looked dirty, I barely wanted to shower. There was hair that did not even belong to me on ...
Reviewed on Mar 29, 2026
Mohegan Sun
1 Mohegan Sun Boulevard Montville CT
9.2/10 Wonderful! (2,043 reviews)
Clean room, very nice staff
Reviewed on Mar 30, 2026
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
The price is CA $99 per night from Apr 5 to Apr 6
CA $99
CA $115 total
Apr 5 - Apr 6
includes taxes & fees
7.2/10 Good! (1,007 reviews)
Great affordable hotel. The hallway has an odor, but there were no issues with the room itself. The bathroom is a bit outdated, but for the value of a night’s stay, I can’t really complain. I’m not a big fan of having to use the side entrances at night because guests aren’t allowed through the front ...
Reviewed on Mar 31, 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.
