Chester Holidays

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Top destinations in Chester

A large, two-story house with a steeply pitched roof and a chimney.
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Chester

Chester

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 S$282 per night from 13 Jul to 14 Jul
S$282
13 Jul - 14 Jul
includes taxes & fees
8.2/10 Very good! (509 reviews)
"I loved the fact that you could stand out on balcony and overlook the entire area. You can walk all around by the ocean where chairs were placed by the water so you could just sit in them, enjoy the hot sun and listen to the ocean while relaxing, watching the clouds sail by, listening to the birds ..."

Reviewed on 28 Jun, 2026

Oak Island Resort & Conference Centre
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 S$240 per night from 12 Jul to 13 Jul
S$240
12 Jul - 13 Jul
includes taxes & fees
9.2/10 Wonderful! (2,172 reviews)
"The hotel is good and clean. This is my second time. The best thing is the staff. They are welcoming and helpful (Eden, Shawna and Libby) were all great."

Reviewed on 28 Jun, 2026

Chateau Bedford, Trademark Collection by Wyndham
Future Inns Halifax

Future Inns Halifax

3 out of 5
30 Fairfax Dr Halifax NS
The price is S$238 per night from 17 Jul to 18 Jul
S$238
17 Jul - 18 Jul
includes taxes & fees
9.2/10 Wonderful! (2,220 reviews)
"Nice and clean"

Reviewed on 30 Jun, 2026

Future Inns Halifax
See all 585 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

Halifax Small Group Premium Tour with Peggy’s Cove

Halifax Small Peggy’s Cove Express

S$96
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

S$222
per adult
Small Group Tour - Peggy's Cove, Lunenburg, the Annapolis Valley
Half-Day Small-Group Tour of Nova Scotia's South Shore

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

S$162
per adult
100% of travellers recommend
Half-Day Small-Group Tour of Nova Scotia's South Shore
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.