Chester Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Chester Vacation Packages

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
The price is AED 768 per night from Apr 7 to Apr 8
AED 768
AED 974 total
includes taxes & fees
7 Apr - 8 Apr
9/10 Wonderful! (1,784 reviews)
"From first arriving to checking out every thing and the staff were very helpful,friendly and caring. I will not hesitate to return and it will be very soon"

Reviewed on 18 March 2025

Mohegan Sun
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 AED 248 per night from Mar 27 to Mar 28
AED 248
AED 289 total
includes taxes & fees
27 Mar - 28 Mar
6.8/10 (1,004 reviews)
"Very nice and staff friendly"

Reviewed on 2 March 2025

Motel 6 New Haven - Branford, CT
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 AED 397 per night from Apr 2 to Apr 3
AED 397
AED 456 total
includes taxes & fees
2 Apr - 3 Apr
9/10 Wonderful! (2,357 reviews)
"Very clean, close to the casino and very polite"

Reviewed on 18 March 2025

Hyatt Place 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.

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 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.

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

Norma Terris Theater

You can enjoy a show at Norma Terris Theater on your trip to Chester. While you're in the area, stroll along the beautiful beaches.

Norma Terris Theater