COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Holidays to Chester

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Chester choose Expedia! Find everything you need to organise your trip to Chester in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top flight + hotel deals in Chester

White Elephant Hotel
Hilton Boston Downtown/Faneuil Hall
Seaport Hotel Boston
The Godfrey Hotel Boston
Porter Square Hotel
Cambria Hotel Boston, Downtown-South Boston

Top 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
The price is £55 per night from 18 Apr to 19 Apr

Situated near the airport, this hotel is 2.4 mi (3.8 km) from Holyoke Mall and 2.5 mi (4 km) from Josiah Day House. MassMutual Center and MGM Springfield are ...

3.7/5Good! (989 reviews)

"Its one of the most comfortable rooms in my opinion."…"

Reviewed on 8 Apr 2021

Red Roof Inn PLUS+ West Springfield
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3 out of 5
100 Congress Street, Springfield, MA
The price is £73 per night from 19 Apr to 20 Apr

This family-friendly hotel is located in the city centre, within 2 mi (3 km) of MGM Springfield, Springfield Armory and Naismith Memorial Basketball Hall of ...

4.1/5Very Good! (1,190 reviews)

"Dunkin in the parking lot"…"

Reviewed on 11 Apr 2021

La Quinta Inn & Suites by Wyndham Springfield MA
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
The price is £103 per night from 15 Apr to 16 Apr

Situated in a state park, this spa hotel is 4.2 mi (6.8 km) from Smith College, and within 12 mi (20 km) of Amherst College and University of Massachusetts-Amherst. ...

4.6/5Wonderful! (966 reviews)

"Music from restaurant is loud if you’re on that side of the building. Buzzed through the hotel room. Nothing was really done to remedy surgery I brought it to their attention either."…"

Reviewed on 12 Apr 2021

D. Hotel Suites & Spa
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.

Top things to do in Chester

Plan your Chester holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Chester. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Chester holiday package?
Your situation can change suddenly, so yes. You may be able to change or cancel your Chester holiday package at no cost within 24 hours of booking. For bookings older than that, you can still cancel and rebook, but your airline, hotel or car rental company may charge additional fees. Need more information? Look up our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.
Where should I stay in Chester?
There’s so much to see in Chester, so spend your nights near its top attractions and treat yourself to more time sightseeing. Chester Town Hall is one spot to put on your itinerary.
When is the best time of year to visit Chester?
You’ll have to consider your priorities to find the right answer. Typically, you’ll nab the best deals in , while is when hotel rates usually rise. Chester draws the crowds in . If you’re hoping for a more relaxed holiday, would be a better time to pack your bags.
How far in advance should I book my Chester holiday?
You’ll be rewarded with the widest variety and the lowest prices by booking your adventure to Chester nice and early. Air carriers usually publish flights anywhere up to 12 months before departure, so reserve your spot as soon as possible. That said, Expedia is committed to providing you with the best bargains around, so it’s never a bad time to book your dream holiday!
What should I know before booking a Chester travel package?
Find deals that fit your budget with an Expedia package. Flights, hotels, rental cars — we’ve got all of them. You’ll save precious dollars just by combining your bookings. Whether you’re going on a ski adventure or venturing someplace warm, your perfect getaway is just a few clicks away.
Does Expedia offer Book Now, Pay Later Chester holiday packages?
Expedia has proudly partnered with online lender Affirm to help reduce any financial concerns to do with your trip. This may be useful if your need to travel has cropped up suddenly. Book Now, Pay Later and split the price of your hotel and activities package booking over numerous installments.