Chester Holidays

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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Packages with flights are ATOL protected

Your Chester Holiday

Make organising your next getaway a breeze with a Chester holiday package. Whether it's the food scene, history or something else entirely that draws you to this destination, our packages will help you discover it all. A carefully planned itinerary is essential for your trip to Chester. Western Shore, Bayswater and Blandford are a few of the most well-known cities here. Expedia has everything you need when it comes to organising your Chester holiday. From hotels and flights, to activities and more, we're here to help you curate a travel experience like no other.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
per person
25 Sept - 2 Oct
found 24 hours ago
Return direct flight included
London (LON) to Halifax (YHZ)
8.2/10 Very Good! (631 reviews)
Easy to find location, clean!

Reviewed on 2 Aug 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
Save 100% on your flight
per person
14 Sept - 20 Sept
found 24 hours ago
Return flight included
Edinburgh (EDI) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Our stay was fabulous! The ho

Reviewed on 25 Jul 2025

Super 8 by Wyndham Windsor NS

Super 8 by Wyndham Windsor NS

2 out of 5
per person
25 Sept - 2 Oct
found 24 hours ago
Return direct flight included
London (LON) to Halifax (YHZ)
8.4/10 Very Good! (1,008 reviews)
Room was very spacious, guest services were great! Pool was Amazing {according to the kids} especially the slide! Breakfast was good. The pancake machine was a hit!!

Reviewed on 31 Jul 2025

Surfside Inn

Surfside Inn

3 out of 5
per person
12 Sept - 22 Sept
found 1 day ago
Return flight included
London (LHR) to Halifax (YHZ)
8.8/10 Excellent! (317 reviews)
It’s just awesome, just book it, you’ll thank yourself. Cheers!

Reviewed on 31 Jul 2025

The Barrington Hotel

The Barrington Hotel

3.5 out of 5
Downtown Halifax
per person
14 Sept - 20 Sept
found 24 hours ago
Return flight included
Edinburgh (EDI) to Halifax (YHZ)
7.8/10 Good! (4,287 reviews)
Location was perfect. Would stay again.

Reviewed on 3 Aug 2025

Chester Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Stanfield Intl. Airport (YHZ)
Top Sights
Saint Margarets Bay, Bayswater Beach Provincial Park and Graves Island Provincial Park

Top hotels in Chester

Moonlight Cottage

Moonlight Cottage

Hubbards, NS
9.6/10 Exceptional! (11 reviews)
A wonderful week stay!
"The view and location can’t be beat! We did day trips to surrounding sites and enjoyed happy hour and dinners with the greatest view ever! Good communication with the owner and a 100% total relaxing visit!"

Reviewed on 6 Jul 2025

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Moonlight Cottage
Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore, NS
9.4/10 Exceptional! (16 reviews)
Comfortable
"Central location. Good visit"

Reviewed on 15 Jul 2025

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Oceanfront Luxury Magical Views Sunset and Sunrise
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
133 Kearney Lake Rd, Halifax, NS
Fully refundableReserve now, pay when you stay
The price is £144 per night from 4 Aug to 5 Aug
£144
4 Aug - 5 Aug
includes taxes & fees
9/10 Wonderful! (1,976 reviews)
"Wonderful stay, comfortable beds and great location!!"

Reviewed on 1 Aug 2025

Chateau Bedford, Trademark Collection by Wyndham
See all 521 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?
Our Chester packages, which begin from just £601, are the easiest way to save. Select your preferred hotels, flights and more to create your ideal itinerary.
If I'm not able to travel, can I cancel my Chester travel package?
We totally get that sometimes life doesn't go according to plan. If you've locked in a Chester travel package and have to amend or cancel it, we're here to help. We recommend browsing our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to cancel or change your itinerary for free. If it's been longer than 24 hours, your hotel, airline or car rental company may charge a fee.
How do I get a cheap travel package to Chester?
Our Chester travel packages offer plenty of savings for the savvy wanderer. For the best deal, simply combine your flights, hotels and extras (including tours) into a budget-friendly package. But low prices are just the beginning of your next amazing adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotel options around the world to select from. No matter your budget, there's a travel package that's perfect for you.
Does Expedia offer Book Now, Pay Later Chester holidays?
We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan best suited to your needs during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all budget sizes, so you can escape on that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip over multiple transactions.
  • Low deposit holidays: When you stumble on an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.

What are the top hotels in Chester?
For properties in Fox Point with friendly service and comfy beds, you can't go past Charming 3 Bedroom Cottage Near Hubbards and Amazing Ocean - View Just Steps To Fox Point Beach. If you plan to explore Chester Basin as well, you can look forward to a solid night's sleep at 4 Bed - - Persons Holiday Rental With Cottage or A Sailors Paradise - Stevens Cove Guest Quarters.
How far in advance should I book my Chester holiday?
While not all airlines release tickets early, you can usually look up international fares on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you've left everything to the last minute, you may still be in luck. Low prices occasionally appear a few weeks prior to departure.
What does an Expedia Chester travel package include?
Hotels, flights and a cool set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a few tours and activities and watch your savings grow. When it comes to crafting your Chester escape, you're in charge!
What should I know before booking a Chester travel package?
A travel package can be easier on the hip pocket than individually booking all you need for your getaway. For example, combine your flights, hotels and rental cars and save a pretty penny. Whatever type of holiday you have in mind, there's bound to be a package within your budget.
Can I choose my airline with a Chester Expedia travel package?
You can, and with more than 550 airlines to pick from throughout 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.