Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chester

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is 2.705.707 ₫ per night from 11 Aug to 12 Aug
2.705.707 ₫
3.111.563 ₫ total
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (2,730 reviews)
"Wonderful experience beginning to end. They had a large wedding party staying at the hotel and still took care of us as if we were just as important. Wonderful stay"

Reviewed on 12 Jul 2026

Hyatt Place Uncasville - Casino Area
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is 2.296.173 ₫ per night from 22 Jul to 23 Jul
2.296.173 ₫
2.640.560 ₫ total
22 Jul - 23 Jul
includes taxes & fees
8/10 Very good! (1,015 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on 11 Jul 2026

Pier Blue Inn Old Saybrook - Essex
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Fully refundableReserve now, pay when you stay
The price is 2.571.735 ₫ per night from 19 Jul to 20 Jul
2.571.735 ₫
2.957.627 ₫ total
19 Jul - 20 Jul
includes taxes & fees
7.4/10 Good! (1,008 reviews)
"Creo que si mantuvieran un poco más limpio . Y el servicio más atento sería mejor . No muy satisfecho.😒"

Reviewed on 12 Jul 2026

Red Roof Inn Meriden
See all 1,096 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday packages? Try to avoid public holidays and any major events.
How many days is enough for Chester?
The ideal length for your Chester holiday 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 holiday package to Chester?
Boasting a host of highlights starting with its excellent hiking, Chester is a good holiday destination. Whether you'd like to visit sights such as Chester Creek Marina and Norma Terris Theatre or take the road less traveled, you'll find loads to see and do on your Chester holiday.
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 holiday package as soon as possible.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester break by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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 accommodation, 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 holiday package.

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