Chester Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 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

Top hotels in Chester

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is ฿3,888 per night from 1 Nov to 2 Nov
฿3,888
฿4,432 total
1 Nov - 2 Nov
includes taxes & fees
8.4/10 Very good! (637 reviews)
"Property is beautiful! Staff are incredibly friendly and helpful. Even in the off season, and things being very quiet I was shocked to see how maintained the different areas were. Watching the sun rise, and set is stunning. We will be back :)"

Reviewed on 30 Oct 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 ฿4,027 per night from 31 Oct to 1 Nov
฿4,027
฿4,728 total
31 Oct - 1 Nov
includes taxes & fees
Future Inns Halifax
Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
98 Chain Lake Dr Halifax NS
Fully refundableReserve now, pay when you stay
The price is ฿3,842 per night from 31 Oct to 1 Nov
฿3,842
฿4,511 total
31 Oct - 1 Nov
includes taxes & fees
Coastal Inn Halifax
See all 636 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.

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

Lunenburg from Bluenose Golf Course

Half-Day Small-Group Tour of Nova Scotia's South Shore

฿4,131
per adult
100% of travellers recommend
Half-Day Small-Group Tour of Nova Scotia's South Shore
Small Group Tour - Peggy's Cove, Lunenburg, the Annapolis Valley

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

฿5,666
per adult
Small Group Tour - Peggy's Cove, Lunenburg, the Annapolis Valley
Halifax Small Group Peggy’s Cove Driving Tour

Halifax Small Group Peggy’s Cove Driving Tour

฿1,865
per adult
96% of travellers recommend
Halifax Small Group Peggy’s Cove Driving 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.