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.

Top destinations in Chester

A white and red lighthouse with a clear blue sky in the background.
FlightsFlightsHotelsHotels

Western Shore

Western Shore

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

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is AU$295 per night from 4 Aug to 5 Aug
AU$295
4 Aug - 5 Aug
includes taxes & fees
8.2/10 Very good! (515 reviews)
"lots of fun activities to do, Outdoor pool excellent"

Reviewed on 9 July 2026

Oak Island Resort & Conference Centre
Future Inns Halifax

Future Inns Halifax

3 out of 5
30 Fairfax Dr Halifax NS
Fully refundableReserve now, pay when you stay
The price is AU$290 per night from 10 July to 11 July
AU$290
10 July - 11 July
includes taxes & fees
9.2/10 Wonderful! (2,266 reviews)
"Clean and mostly quiet"

Reviewed on 9 July 2026

Future Inns Halifax
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 AU$268 per night from 12 July to 13 July
AU$268
12 July - 13 July
includes taxes & fees
9.2/10 Wonderful! (2,194 reviews)
"Best hotel breakfast! Very clean and great staff. Had an issue with the bathroom faucet and they moved us to another room right away which was great. Perfect for short stays and only 20 min from downtown Halifax."

Reviewed on 9 July 2026

Chateau Bedford, Trademark Collection by Wyndham
See all 592 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.

Stay near popular Chester attractions

Bayswater Beach Provincial Park

9.0/10 (26 reviews)
If a restful holiday is part of your travel plans, Bayswater Beach Provincial Park might be the perfect place to visit during your trip to Bayswater. Make some time to visit the monuments while you're in the area.
See properties

What to do in Chester

Halifax Small Group Premium Tour with Peggy’s Cove

Halifax Small Peggy’s Cove Express

AU$111
per adult
96% of travellers recommend
Halifax Small Peggy’s Cove Express
Small Group Tour - Peggy's Cove, Lunenburg, the Annapolis Valley

Small Group Tour - Peggy's Cove, Lunenburg, the Annapolis Valley

AU$245
per adult
Small Group Tour - Peggy's Cove, Lunenburg, the Annapolis Valley
Peggys Cove Sunset Tour

Peggys Cove Sunset Tour

AU$109
per adult
Peggys Cove Sunset Tour
See all activities in Chester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.