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
Beechmont - Perfect for Family Retreat!
Hyatus Luxury Residences City Crossing
Luxury Furnished Apartments by Hyatus Downtown at Yale
Heritage Hotel, Golf & Conference Center

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Chester Hotel Deals

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
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

Hyatt Place Uncasville - Casino Area
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
9.2/10 Wonderful! (2,043 reviews)
Clean room, very nice staff

Reviewed on Mar 30, 2026

Mohegan Sun
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
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 The bathroom is a bit outdated, but for the value of a night’s stay, I can’t really complain.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

Motel 6 New Haven - Branford, CT
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.