Chester Vacations from $606

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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.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $739, price is now $606 per person
$606
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.2/10 Very Good! (1,008 reviews)
Nice size room and very clean. Great price!

Reviewed on Oct 13, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $3,629, price is now $2,594 per person
$2,594
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,976, price is now $1,462 per person
$1,462
per person
Dec 24 - Dec 29
found 3 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9.4/10 Exceptional! (316 reviews)
Beautiful beach property that gives you such a feeling of luxury all around you. Staff has been great, very clean hallways and entire property. Balcony is beautiful!

Reviewed on Oct 14, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $939, price is now $757 per person
$757
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (877 reviews)
Loud tv in adjoining room, went on late, but i covered my head with a pillow

Reviewed on Oct 11, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $1,043, price is now $849 per person
$849
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Loud partying and screaming most of the night outside. Hotel was ok but not near as nice as most Omni’s.

Reviewed on Oct 12, 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

Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Fully refundableReserve now, pay when you stay
$211 nightly
The price is $239 total per night from Oct 22 to Oct 23
$239 total
Oct 22 - Oct 23
Total with taxes and fees
9/10 Wonderful! (2,021 reviews)
"Beautiful !"

Reviewed on Oct 11, 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
$103 nightly
The price is $118 total per night from Oct 28 to Oct 29
$118 total
Oct 28 - Oct 29
Total with taxes and fees
9/10 Wonderful! (2,591 reviews)
"Nice place that was last updated in the 1980s and it shows."

Reviewed on Oct 12, 2025

Hyatt Place Uncasville - Casino Area
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
1954 Norwich New London Tpke, Route 32, Montville, CT
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $83 total per night from Nov 2 to Nov 3
$83 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,801 reviews)
"The girl at the front desk was very helpful and pleasant and I appreciated being able to check in a little early"

Reviewed on Oct 13, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area
See all 1,040 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.

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 $606 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.