Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

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! (82 reviews)
Peaceful Relaxing close to Nature
"Four Seniors getting together for a reunion"

Reviewed on 30 May 2025

Get rates
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
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 NZ$278 per night from 29 June to 30 June
NZ$278
29 June - 30 June
includes taxes & fees
9.2/10 Wonderful! (1,672 reviews)
"Clean and organized. Plenty amount of shampoo etc. High ceiling, clean 100% cotton bed sheets. Professional front desk manners are some that i liked."

Reviewed on 20 Jun. 2025

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 NZ$285 per night from 22 June to 23 June
NZ$285
22 June - 23 June
includes taxes & fees
9/10 Wonderful! (1,922 reviews)
"Staff was great- nice and quiet location. Breakfast was always good"

Reviewed on 21 Jun. 2025

Chateau Bedford, Trademark Collection by Wyndham
See all 508 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.

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.