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
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
36 Treasure Drive Western Shore NS
Fully refundableReserve now, pay when you stay
AU$238
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very good! (556 reviews)
"Clean room, helpful staff. Great location and amenities. Outdoor fire pits, nice outdoor roof top patio. Beautiful water view. Only thing for me was my room was close to the lobby and if you needed to go to bed early and get up early the live entertainment went until 11pm. It was loud enough that ..."
Reviewed on 22 Aug 2026
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Chester NS
9.8/10 Exceptional! (42 reviews)
"Amazing views/ Clean & relaxing place to stay!"
Reviewed on 20 Aug 2026
Future Inns Halifax
30 Fairfax Dr Halifax NS
AU$267
13 Sept - 14 Sept
includes taxes & fees
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.
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.
Oak Island
9.0/10 (95 reviews)
Commune with nature and explore the great outdoors at Oak Island during your travels in Martins Point.
Chester Golf Club
8.4/10 (28 reviews)
Enjoy a round of golf in Chester at Chester Golf Club. Stroll along this family-friendly area's waterfront or simply enjoy its seafood restaurants.
Chester Playhouse
8.6/10 (12 reviews)
You can enjoy a show at Chester Playhouse on your trip to Chester. Stroll along this family-friendly area's waterfront or simply enjoy its seafood restaurants.
Graves Island Provincial Park
8.6/10 (9 reviews)
Commune with nature and explore the great outdoors at Graves Island Provincial Park during your travels in East Chester. Stroll along the seaside or experience the entertainment venues in this family-friendly area.
Ross Farm Museum
9.0/10 (2 reviews)
You can browse the exhibits at Ross Farm Museum, a museum with a storied past, during your trip to New Ross. Amble around the area's parks or experience its museums.
Little Lake
Commune with nature and explore the great outdoors at Little Lake during your travels in The Lodge.
What to do in Chester
Halifax Small Group Peggy’s Cove Driving Tour
AU$68
per adult
96% of travellers recommend
Half-Day Small-Group Tour of Nova Scotia's South Shore
AU$177
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
