Chester Vacations from $433

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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.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
per person
Aug 14 - Aug 17
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8.8/10 Excellent! (758 reviews)
Well-located, clean, newer, reasonably-priced lodging. Comfortable bed and room. Very nice lobby and bar. Hot water was not very hot in shower.

Reviewed on Jun 18, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Aug 21 - Aug 24
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Hotel should offer daily free complimentary water bottles due to very hot weather

Reviewed on Jun 18, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Aug 17 - Aug 20
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (820 reviews)
Such detail to everything - amazing

Reviewed on Jun 12, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
per person
Aug 17 - Aug 20
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
9.6/10 Exceptional! (15 reviews)
Phenomenal property. Beautiful room and great amenities. Great communication.

Reviewed on Jun 18, 2025

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

3 out of 5
The Centre
per person
Aug 17 - Aug 20
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
9.6/10 Exceptional! (302 reviews)
This is our favorite place to stay. 10 out of 10

Reviewed on Jun 19, 2025

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Discover the most popular places to visit in Chester

Chester Creek Marina

Explore the waterfront in Chester with a trip to Chester Creek Marina. While you're in the area, stroll along the beautiful beaches.

Chester Creek Marina

Chester Hotel Deals

Motel 6 New Haven - Branford, CT
Motel 6 New Haven - Branford, CT
2 out of 5
320 E Main St, Branford, CT
Fully refundable
$72 nightly
The price is $83 total per night from Jun 24 to Jun 25
$83 total
Jun 24 - Jun 25
Total includes taxes and fees
6.8/10 (1,000 reviews)
"Inexpensive, clean, and available on very short notice after a minor travel interruption. We were quite satisfied with the accommodations."

Reviewed on Jun 18, 2025

Motel 6 New Haven - Branford, CT
Mohegan Sun
Mohegan Sun
4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $242 total per night from Jun 23 to Jun 24
$242 total
Jun 23 - Jun 24
Total includes taxes and fees
9/10 Wonderful! (1,911 reviews)
"ThNks"

Reviewed on Jun 18, 2025

Mohegan Sun
Hyatt Place Uncasville - Casino Area
Hyatt Place Uncasville - Casino Area
3 out of 5
2049 Norwich, New London Turnpike, Montville, CT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Jun 29 to Jun 30
$116 total
Jun 29 - Jun 30
Total includes taxes and fees
9/10 Wonderful! (2,436 reviews)
"Very nice place literally and delicious breakfast"

Reviewed on Jun 16, 2025

Hyatt Place Uncasville - Casino Area
See all 1,062 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 $433 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.