Chester Holidays

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Photo by Elizabeth Massa Peroulakis

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Your Chester Holiday

Our holiday packages to Chester allow you to create your own adventure. Tailor your getaway to your needs and interests and make every moment count in this fantastic city. There's a whole load to see during a trip to Chester, including Becket Land Trust Historic Quarry and Chester Town Hall. Check out Expedia's wide range of travel options and book your ultimate holiday to Chester today.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
630
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Blandford Ski Area, Maple Corner Farm Cross Country Ski Area and Chester Town Hall

Our pick of the best Chester Hotel Deals

Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Stay at this hotel in West Springfield. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their ...
6.8/10 (1,002 reviews)
"Amazing space clean and well maintained"

Reviewed on 10 Jun 2025

Red Roof Inn PLUS+ West Springfield
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants and room service. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (2,268 reviews)
"It was the perfect stay for our family for a night! It was so clean, everyone was kind, the breakfast was AMAZING & so was the indoor pool! Highly recommend!"

Reviewed on 15 Jun 2025

D. Hotel Suites & Spa
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
Stay at this golf hotel in West Springfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
7/10 Good! (1,009 reviews)
"I like everything cleanness, pool,staff especially very professional, cleanness of room,plus quiet ,ac runs great"

Reviewed on 16 Jun 2025

Quality Inn West Springfield
See all 829 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Chester holiday with Expedia?
With top-value flights, accommodation and car hire choices all in one convenient place, Expedia makes arranging your Chester break a cinch. Moreover, we can help you bundle your bookings into a package holiday so you can get even more savings. Choose from wonderful escapes, add your flights and/or a hire car (and maybe also some exciting activities!) and land unbeatable prices. Had a change of plans? Expedia offers a flexible cancellation policy for many reservations. To discover more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Chester?
June, July and August are the busiest months in Chester, while November, December and January are generally quieter. Organise your visit to Chester according to what style of holiday you want. January is the coolest month, when average daytime temperatures are -4ºC. In July, the warmest month, expect averages of 21ºC during the day.
What is the top hotel for my holiday in Chester?
Kick back and relax in Chester by choosing D. Hotel Suites & Spa as your gateway to adventure and fun.
How do I get a cheap holiday to Chester?
Secure flights that suit your busy schedule, add a hotel room to your booking and watch the savings pile up with a Chester holiday. It's as simple as that! From hotels and flights to tours and hire cars, Expedia makes travelling cheaply a cinch. And with over 400 air carriers and 321,000 hotels around the world to choose from, you won't be short of choice. Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Chester holiday?
From Chester Town Hall to Blandford Ski Area, there's an array of exciting things to do and see during a holiday in Chester. Stop by this city's numerous other attractions if you're here for a while.
What is the best area to stay in when on holiday in Chester?
Chester has lots of popular places to discover, like Chester Town Hall. Stay somewhere near this attraction and make sightseeing hassle-free.
Do I need a visa for my Chester holiday?
Look up the latest rules on official government websites. Your nationality and whether you're travelling for study, business or leisure will determine if you need a visa for Chester. Make yourself familiar with the application process, including the required documentation, turnaround times and fees. Finalise your application well in advance to allow enough time for processing. Some visas may take many weeks or even months to obtain, depending on the country.
What should I wear on my Chester holiday?
Though everyone's style differs, it can be useful to have a few guidelines for what kind of clothes to wear on your holiday in Chester. We recommend browsing style blogs before you head off for inspiration on fashion trends or dress codes. Daytime temperatures during January, Chester's coolest month, average around -4ºC. July marks this destination's warmest month when the average daily temperature reaches 21ºC. Our top tip? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Chester holiday include?
Hotels, flights and car hires, or any combination of the three --- the choice is all yours! Whether you're headed to Chester on a family road trip or enjoying a solo break, there's a bundle to match every budget and style. Once you've made your booking, why not add on one or two tours as well? Apartments and private holiday homes are a few popular property types in Chester. No matter your preference or size of your group, you can rely on Expedia for the flexibility and freedom to tailor your escape.
Does Expedia offer Book Now, Pay Later Chester holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply select the payment plan that suits best during the checkout process and take the stress out of budgeting for your trip. Remember to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:
  • Pay monthly holidays: If paying across multiple transactions works for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
  • No-deposit holidays: Clicking the "book now" button is much easier with this payment plan. With no deposit required for your getaway, you can Book Now, Pay Later and start packing your suitcase.

Can I choose my airline with a Chester Expedia holiday?
You can, and with over 400 airlines to select from all over the world, you're spoiled for choice. Have a look through the available options and see which airline best suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.