Chester Trips (flight + hotel)

Photo by Annette Babek

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Top hotels in Chester

Motel 6 New Haven - Branford, CT
Motel 6 New Haven - Branford, CT
2 out of 5
320 E Main St, Branford, CT
Fully refundable
The price is P4,070 per night from Jun 26 to Jun 27
P4,070
P4,738 total
Jun 26 - Jun 27
includes taxes & fees
6.8/10 (1,002 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
The price is P10,805 per night from Jun 23 to Jun 24
P10,805
P13,852 total
Jun 23 - Jun 24
includes taxes & 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
The price is P5,786 per night from Jun 29 to Jun 30
P5,786
P6,653 total
Jun 29 - Jun 30
includes taxes & fees
9/10 Wonderful! (2,431 reviews)
Extremely Pleased
"Everyone there is very friendly and helpful. You have a professional staff well trained!"

Reviewed on Jun 18, 2025

Hyatt Place Uncasville - Casino Area
See all 1,064 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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.