Chester Vacations from $408

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $532, price is now $408 per person
$408
per person
Sep 18 - Sep 21
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again.

Reviewed on Jul 7, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $746, price is now $545 per person
$545
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
9.2/10 Wonderful! (998 reviews)
steps out front and no parking, but clean

Reviewed on Jul 3, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,139, price is now $834 per person
$834
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $682, price is now $518 per person
$518
per person
Sep 18 - Sep 21
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
9.2/10 Wonderful! (2,191 reviews)
Nice hotel, good location, helpful staff

Reviewed on Jul 7, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,491, price is now $1,169 per person
$1,169
per person
Aug 20 - Aug 24
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
the room and amenities are well maintained, clean and convenient, the customer service is awesome , answering requests fast and responsive.

Reviewed on Jul 5, 2026

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Stay near popular Chester attractions

Norma Terris Theater

The Norma Terris Theatre is Goodspeed Musicals' developmental space where innovative productions debut. In this intimate setting, audiences witness tomorrow's Broadway hits evolve before their eyes.
See properties

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
$98 nightly
The price is $113 total per night from Jul 19 to Jul 20
$113 total
Jul 19 - Jul 20
Total with taxes and fees
9/10 Wonderful! (2,708 reviews)
"breakfast was good hot and cold"

Reviewed on Jul 7, 2026

Hyatt Place Uncasville - Casino Area
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $106 total per night from Jul 12 to Jul 13
$106 total
Jul 12 - Jul 13
Total with taxes and fees
7.4/10 Good! (1,004 reviews)
"Clean room"

Reviewed on Jul 7, 2026

Red Roof Inn Meriden
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $115 total per night from Jul 14 to Jul 15
$115 total
Jul 14 - Jul 15
Total with taxes and fees
8/10 Very Good! (1,009 reviews)
"Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again."

Reviewed on Jul 7, 2026

Pier Blue Inn Old Saybrook - Essex
See all 1,096 properties in Chester
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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
1,550
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park

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Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from $408 on Expedia, you'll be thrilled with how little a vacation to Chester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chester?
If you're looking to score a cheap Chester vacation package, consider planning a trip in December, January and February. You'll typically find better rates on flights and accommodations during these months — perfect for budget-conscious travelers.
How many days is enough for Chester?
With a well-organized itinerary, you can easily hit the main Chester sights in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
Known for its hiking and home to popular attractions like Chester Creek Marina, a Chester vacation is sure to leave an impression. Another top sight to check out? Don't miss Norma Terris Theater.
How to find the best Chester package deals?
Use Expedia's filters to find some unbeatable Chester package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Chester package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
Score fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chester escape.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester getaway is meant to be an escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.