Chester Holidays from £1,246

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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.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was £2,097, price is now £1,246 per person
£1,246
per person
16 Sept - 23 Sept
found 19 hours ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
We loved the Atlas Hotel, located directly opposite Harvard on a quiet street in Boston. It is a beautifully appointed hotel with good-sized rooms (we took a corner room and were very happy with it), and it is well-suited to international travellers (space for bags, etc). The bed is comfortable, and the rooms are well serviced and clean throughout our stay, with lovely linens, towels, etc. We did have a good hairdryer, essential for me (long hair) and a steamer. We did ask for an iron and ironing board. The iron was super, but the ironing board had seen better days! This was mentioned and replaced quickly. What makes this hotel are the staff; they are friendly, always say hello, and ask if they can help, which made it a pleasure to be here and stay here. This was in the middle of the World Cup, so I can imagine they were busy with many travellers arriving and leaving. We liked the tasty breakfasts and the great cocktails on the top floor of the hotel, which has a good view over the Boston environs. I would be delighted to stay here again in the future. A special place where you feel special for being here.

Reviewed on 10 Jul 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £3,065, price is now £1,781 per person
£1,781
per person
23 Aug - 30 Aug
found 20 hours ago
Return direct flight included
London (LHR) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on 11 Jul 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was £2,124, price is now £1,285 per person
£1,285
per person
27 Aug - 1 Sept
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
The staff and amenities at The Nantucket Inn were excellent. In particular, we give a 'shout out' to Balford, who went the extra mile (more than once!) to ensure that my physically challenged husband was accommodated in the best possible and most comfortable way during our transportation to/from town, and to Lisa at the front desk, who was responsive and speedy to our every request for information. Convenient access to the airport (walking-distance) was a bonus, as was the availability of delicious breakfast options (for a cost) and evening cocktails. The kiddoes enjoyed both pools. We would choose to stay here again.

Reviewed on 11 Jul 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was £2,562, price is now £1,596 per person
£1,596
per person
27 Aug - 1 Sept
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
9.4/10 Exceptional! (720 reviews)
Beautiful area with private beach

Reviewed on 11 Jul 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was £3,556, price is now £2,316 per person
£2,316
per person
25 Sept - 2 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (576 reviews)
Good location

Reviewed on 10 Jul 2026

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

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 £97 per night from 19 Jul to 20 Jul
£97
19 Jul - 20 Jul
includes taxes & fees
8.2/10 Very good! (2,104 reviews)
".."

Reviewed on 11 Jul 2026

La Quinta Inn & Suites by Wyndham Boston-Andover
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St Manchester NH
Fully refundableReserve now, pay when you stay
The price is £81 per night from 19 Jul to 20 Jul
£81
19 Jul - 20 Jul
includes taxes & fees
8.2/10 Very good! (1,405 reviews)
"Lobby entrance stairs looked like something from a movie or really upscale hotel! Everything was great except the 2nd floor hallway which had a slight stale cigarette smell and the carpet was quite frayed at the turn in the hall which could make a tripping hazard."

Reviewed on 11 Jul 2026

Best Western Plus Executive Court Inn & Conference Center
La Quinta Inn & Suites by Wyndham Salem NH

La Quinta Inn & Suites by Wyndham Salem NH

3 out of 5
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
The price is £82 per night from 2 Aug to 3 Aug
£82
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very good! (1,276 reviews)
"Our room was close to the elevator -room 210, and unfortunately we heard the elevator a lot in the early morning. That was our only complaint-everything else was great!"

Reviewed on 12 Jul 2026

La Quinta Inn & Suites by Wyndham Salem NH
See all 495 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.
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Stay near popular Chester attractions

Chester Town Hall

After visiting Chester Town Hall, make a plan to see the other sights and activities in Chester.
See properties

Frequently asked questions

How much does a Chester travel package cost?
From as little as £1,246, 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.

Explore a world of travel with Expedia

* 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.