Chester Holidays

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Your Chester Holiday

Make planning your next getaway quick and easy with a Chester holiday package. Whether it's nature, history or something else entirely that lures you here, our package deals will help you experience it all. Why not organise your trip to Chester around its top cities? Western Shore, Bayswater and Blandford are all great places to start. Start packing your suitcase, because your Chester holiday is only clicks away with Expedia.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Chester Essential Information

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

Our pick of the best Chester Hotel Deals

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Hubbards
9.8/10 Exceptional! (81 reviews)
Idyllic cottage on the shore
"Bring your groceries and leave your worries behind. This out-of-the-way vacation cottage is a great place to settle in and watch the waves. We spotted seals, eagles and fishing boats gliding past. The road onto the island, with it's twists, turns and one-lane bridge, adds to the charm. The property ..."

Reviewed on 2 Nov. 2024

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Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Moonlight Cottage
Moonlight Cottage
Hubbards
9.6/10 Exceptional! (6 reviews)
Beautiful
"We loved the spot and would love to stay again!"

Reviewed on 18 Sep. 2024

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Moonlight Cottage
RYA - 2023 - 24 - 03281153042804049 - 20<br>House with four bedrooms and deck
RYA - 2023 - 24 - 03281153042804049 - 20<br>House with four bedrooms and deck
Hubbards
7.8/10 Good! (8 reviews)
Great view
"Great house. Some of the furniture needs changing like the dining room chairs that are very wobbly.3 bedrooms in basement are only doubles so like my son and his wife that are bigger people they had to sleep separately. All in all there was a great view and it was worth the prixe."

Reviewed on 28 Aug. 2024

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RYA - 2023 - 24 - 03281153042804049 - 20<br>House with four bedrooms and deck
See all 468 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

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Chester holiday package cost?
Starting from just , a holiday package is your ticket to inexpensive travel. Customize your Chester adventure by selecting from our comprehensive range of flights, hotels and rental cars.
How do I get a cheap travel package to Chester?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Hotels, flights, activities and rental cars — we’ve got it all. Select the combination that best suits you and watch your savings grow. We know a package deal is never a one-size-fits-all. That’s why we offer more than 550 airlines and 1 000 000 hotel options globally, which lets you customize your Chester holiday.
What are the top hotels in Chester?
For properties in Deep Cove with cosy beds and friendly service, you can’t go past Oak Island Resort & Conference Centre and On The Beautiful South Shore Near Chester And Hubbards. If you’re stopping by Fox Point as well, you can look forward to a relaxing night’s sleep at Rya - 2023 - 24 - 03281153042804049 or Oceanfront Family Cottage - 5mins From Beach.
How far in advance should I book my Chester holiday?
While prices fluctuate, we generally advise booking your seats as soon as possible. Many international airfares can be found on Expedia up to 12 months in advance. If you’re booking last minute, you might still be in luck. Discount prices to Chester occasionally appear just weeks before departure.
What does an Expedia Chester travel package include?
Hotels, flights and car rentals — we bring you all the best deals. All you have to do is pick and choose your ideal combination. Once you’ve made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to craft an unforgettable Chester getaway.
What should I know before booking a Chester travel package?
When you book your hotels, flights and car rentals together, you’ll nab awesome discounts. Whether you’re planning a mountain getaway in a cabin or prefer to stay in a comfortable hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Chester Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Simply choose the carrier that suits you and create your ideal Chester escape.
If I'm not able to travel, can I cancel my Chester holiday package?
It is possible to cancel your Chester booking if your plans have been upended. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.