Chester Holidays

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Your Chester Holiday

When a getaway to the city is calling, answer it with a Chester holiday package. The neighbourhood of Essex Village, which is great for walking, hiking and views, makes a wonderful base for your adventures. A trip to Chester is a great opportunity to go sightseeing. Make sure you visit renowned attractions like Essex Steam Train, Goodspeed Opera House and Essex Island Marina. Your perfect Chester holiday is a couple of clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

Chester Holiday

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
1,550
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Goodspeed Opera House, Harveys Beach and Devils Hopyard State Park

Our pick of the best Chester Hotel Deals

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 AU$131 per night from 24 Aug to 25 Aug
AU$131
24 Aug - 25 Aug
includes taxes & fees
6.8/10 (1,003 reviews)
"For the low price, this place was fine for one night. There are no amenities (no fridge in the room, no fitness room, no breakfast) but again, you get what you pay for. Otherwise the room was fine and it got the job done."

Reviewed on 4 Aug. 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 AU$355 per night from 2 Sept to 3 Sept
AU$355
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,956 reviews)
"Went for a quick getaway. Everyone and everything was great. Will be back to getaway again."

Reviewed on 17 Aug. 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 AU$228 per night from 1 Sept to 2 Sept
AU$228
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (2,523 reviews)
"Great hot breakfast buffet with a lot of options. Staff was very friendly and the hotel was very clean. Easy check in and out process."

Reviewed on 16 Aug. 2025

Hyatt Place Uncasville - Casino Area
See all 1,059 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

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