Chester Vacations

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Find the Best Chester Vacation Packages

Chester Hotel Deals

Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

269 North Frontage Road New London CT
Fully refundableReserve now, pay when you stay
NT$3,083
NT$3,545 total
Sep 28 - Sep 29
includes taxes & fees
Regency Inn & Suites New London, Mystic
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
NT$2,483
NT$2,856 total
Sep 28 - Sep 29
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
NT$3,493
NT$4,017 total
Oct 5 - Oct 6
includes taxes & fees
9/10 Wonderful! (2,769 reviews)
"Room was very clean and staff was friendly and helpful. No shuttle service to the casino weekdays. The complimentary breakfast was OK ... not a lot of choices. While I didn't expect real table ware, the low quality paper plates and utensils were a negative. Average quality paper plates and utensils ..."

Reviewed on 2026/9/25

Hyatt Place Uncasville - Casino Area
See all 1,108 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.

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

Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals 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?
The off-season is the best time to head to Chester if you're trying to save. Another tip for scoring cheap Chester vacation packages? Try to avoid public holidays and any major events.
How many days is enough for Chester?
The ideal length for your Chester vacation depends on what you'd like to see. Typically, a few days to a week will give you time to go to all the main sights and discover some hidden treasures along the way.
Is it worth booking a vacation package to Chester?
Boasting a host of highlights starting with its excellent hiking, Chester is a good vacation destination. Whether you'd like to visit sights such as Chester Creek Marina and Norma Terris Theater or take the road less traveled, you'll find loads to see and do on your Chester vacation.
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.
How to plan a trip to Chester?
  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Chester.
  2. Plan your budget wisely: In addition to the price of your accommodations, you should consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Chester.
  3. Work out your trip length: Think about how much time you want to spend exploring Chester. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Chester vacation package.

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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.