Chester Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Chester Vacation Packages

Chester Hotel Deals

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
The price is AEDĀ 364 per night from Nov 30 to Dec 1
AEDĀ 364
AEDĀ 418 total
30 Nov - 1 Dec
includes taxes & fees
9/10 Wonderful! (2,816 reviews)
"Our favorite place to stay in the area."

Reviewed on 11 November 2026

Hyatt Place Uncasville - Casino Area
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
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Mohegan Sun
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
The price is AEDĀ 300 per night from Nov 17 to Nov 18
AEDĀ 300
AEDĀ 345 total
17 Nov - 18 Nov
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
See all 1,109 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.
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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices on Expedia for your Chester break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
Travel in the low or shoulder season and you're likely to score cheap Chester vacation packages. Remember that school vacation periods and major events and festivals can have an impact on prices, so do a little research before you go.
How to find the best Chester package deals?
Use Expedia's filters to help you find some of the best Chester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Chester package deals in the low season. Switch up your travel dates and you may land even bigger 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 retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chester?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester trip.
How to plan a trip to Chester?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to travel to Chester.
  2. Set a budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Chester. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Determine how many days away: Start by listing all the activities and attractions you'd like to get to in Chester. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Chester vacation package that brings all your bookings together.