Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Rachel Kent

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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 NS
9.8/10 Exceptional! (98 reviews)
Great host and great property! You cannot beat the ocean views!

Reviewed on 27 Sept 2025

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Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
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$204 per night from 11 Jan to 12 Jan
NZ$204
11 Jan - 12 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (2,112 reviews)
Fresh hot breakfast was a surprise as most places dont offer it

Reviewed on 14 Dec 2025

Chateau Bedford, Trademark Collection by Wyndham
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$197 per night from 14 Jan to 15 Jan
NZ$197
14 Jan - 15 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (2,034 reviews)
Good

Reviewed on 12 Dec 2025

Future Inns Halifax
See all 550 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.