Chester Vacations from $514
Book a Hotel + Flight or Car together to unlock savings
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.
Landing Apartments New Haven Near Dixwell
Newhallville
$873
per person
Dec 30 - Jan 2
found 21 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Landing Furnished Apartment Near Yale University
Downtown New Haven
$747
per person
Dec 30 - Jan 2
found 21 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
2/10 (2 reviews)
Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent
Reviewed on Sep 14, 2026
Hyatus Luxury Residences City Crossing
The Hill
$770
per person
Dec 30 - Jan 2
found 21 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
Fast and effective check-in, great amenities in the building. Kitchen well furnished.
Overall great experience.
Reviewed on Oct 11, 2026
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.
Chester Hotel Deals
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
$110 nightly
$127 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (2,795 reviews)
"I appreciated that this hotel allowed pets to stay with you, as I had a last minute emergency and needed to take one of my dogs with me on my trip. The hotel remained clean despite seeing many dogs come through, so I can tell they do a lot to maintain it. The room itself was exactly what I wanted, ..."
Reviewed on Oct 23, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$214 nightly
$246 total
Oct 27 - Oct 28
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Great"
Reviewed on Oct 21, 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.
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 $514 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.