Chester Holidays from £652

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Your Chester Holiday

With plenty of highlights as well as some hidden gems, this city is best explored with a Chester holiday package. Find a place to stay in Downtown Manchester, which is great for cafes, history and bars and pubs. There's plenty to see and do during your trip to Chester, including Zorvino Vineyards and Robert Frost Farm State Historic Site. No matter your travel plans or the size of your budget, organising your ultimate tailored Chester holiday is a cinch with Expedia.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,132 reviews)
I would stay here again! The rooms are as small as advertised - but the WAY that they utilize the space is truly thought-out. Every space has a purpose and we really loved that we had to be mindful of the space given. The embed was comfy, the room amenities are fantastic, the rainfall showerhead is so nice and the towel warmer is honestly the nicest touch! We'll be back for sure!

Reviewed on 9 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
24 Sept - 29 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
11 Sept - 16 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 25 Jul 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
11 Sept - 16 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (571 reviews)
Washer/Dryer did not work properly. Despite 2 calls and 1 email to customer service, the issue was not resolved. The washer didn’t rinse clothing out and they remained sopping wet. They required extensive drying time as a result ( over 4 hours). This was extremely inconvenient.

Reviewed on 2 Aug 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
27 Oct - 2 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
9.4/10 Exceptional! (360 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on 4 Aug 2025

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
5,200
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Canobie Lake Park, Bear Brook State Park and Zorvino Vineyards

Top hotels in Chester

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St., Manchester, NH
Fully refundableReserve now, pay when you stay
The price is £92 per night from 24 Aug to 25 Aug
£92
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"It was nice, but they did not have coffee in the morning, and the shower was moldy. Those would be what makes me call it good instead of excellent."

Reviewed on 8 Aug 2025

DoubleTree by Hilton Manchester Downtown
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive, Manchester, NH
Fully refundable
The price is £88 per night from 21 Aug to 22 Aug
£88
21 Aug - 22 Aug
includes taxes & fees
8.8/10 Excellent! (853 reviews)
"Very nice and new and clean! Great pool!"

Reviewed on 5 Aug 2025

Even Hotels Manchester Airport by IHG
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd, Andover, MA
Fully refundableReserve now, pay when you stay
The price is £105 per night from 1 Sept to 2 Sept
£105
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (1,819 reviews)
"The staff is very friendly and always cleaning, the breakfast is very good, hot and always restocked promptly. I come here evey year and never had a bad experience"

Reviewed on 6 Aug 2025

La Quinta Inn & Suites by Wyndham Boston-Andover
See all 440 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

How much does a Chester travel package cost?
From as little as £652, you can customize your Chester package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Chester travel package?
It is possible to cancel your Chester booking if your plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
How do I get a cheap travel package to Chester?
Lock in flights that suit your busy schedule, add a hotel room to your booking and watch how much you save with a Chester travel package. It's as simple as that! From flights and hotels to rental cars and activities, Expedia makes travelling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 hotels worldwide to select from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Chester holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply click on the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Don't forget to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all types of budgets, so you can book that well-earned holiday now.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this plan. Just put down a small deposit on your holiday and then start packing your suitcase.

What are the top hotels in Chester?
Get your trip off to a good start by booking a stay at Green Granite Inn. It's one of most popular properties in Chester. Another cosy option is Hampton Inn & Suites Portsmouth Downtown.
How far in advance should I book my Chester holiday?
It can be tricky to know when the best time is to book your trip to Chester. But generally the earlier you book, the lower the prices. In some cases, you can secure your flights and hotels up to a year prior to your departure date. If you're eager to escape on a last-minute getaway, no need to stress! There are incredible bargains featured on Expedia every day.
What does an Expedia Chester travel package include?
With Expedia, you can select a combination of flights, car rentals and hotels to create your ideal Chester travel package. Once you've made your booking, you can add on the fun things like activities and tours. Remember — the more you bundle, the more cash you'll save!
What should I know before booking a Chester travel package?
You can look forward to saving with an Expedia travel package. Combine your airfares, rental cars and hotels and unlock exciting discounts. You're not restricted to hotels, though. Book with us and take your pick of beachside villas, city apartments and even houseboats and castles!
Can I choose my airline with a Chester Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our travel packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.

* 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.