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Holidays to Chester

Accommodation, flights, car rentals, things to do and more - for your holiday in Chester choose Expedia! Find everything you need to organise your trip to Chester in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top Hotel Deals

Windjammer Motel
Windjammer Motel
2.5 out of 5
4070 Nova Scotia Trunk 3, Chester, NS
The price is £63 per night from 19 Jan to 20 Jan

Located in the heart of Chester, this motel is within a 15-minute walk of Lordly House Museum and St. Stephen's Church. Chester Art Center and Chester Playhouse ...…

3.9/5Very Good! (61 reviews)

"THE MOTEL IS OLD BUT IT IS CLEAN AND WELL LOOKED AFTER .....SOME AMENITIES ARE MISSING BUT IT DOES NOT MAKE THE STAY UNCOMFORTABLE"…"

Reviewed on 10 Jul 2020

Windjammer Motel
Sandy Cove Cottage / Chester / Oceanfront / Private Beach and Wharf / Kayak
Sandy Cove Cottage / Chester / Oceanfront / Private Beach and Wharf / Kayak
29 Hebbs Ln, Chester, NS

Situated by the ocean, this cottage is within 6 miles (10 km) of Lordly House Museum, St. Stephen's Church and Chester Art Center. Amicus Gallery and Chester ...…

4.9/5Exceptional! (20 reviews)
A laid-back paradise!

"The property is an absolute gem.. I was lucky to watch the leaves turn bright reds and yellows as fall settled in over my stay. Jane, Kathy and neighbour Jim made my two weeks so easy and wonderful. I wished that the kayaks and dock (float) were still out but I understood that they had already been ..."…"

Reviewed on 11 Nov 2020

Sandy Cove Cottage / Chester / Oceanfront / Private Beach and Wharf / Kayak
DELIGHTFUL WATERFRONT 2BR/2BA HOME IN CHESTER'S BACK HARBOUR W/DOCK.
DELIGHTFUL WATERFRONT 2BR/2BA HOME IN CHESTER'S BACK HARBOUR W/DOCK.
143 Walkers Rd., Chester, NS

Situated on the beach, this historic cottage is within 1 mile (2 km) of Lordly House Museum, St. Stephen's Church and Chester Art Center. Chester Playhouse and ...…

5/5Exceptional! (5 reviews)
Right on the water

"Great spot on the water in Chester."…"

Reviewed on 18 Aug 2020

DELIGHTFUL WATERFRONT 2BR/2BA HOME IN CHESTER'S BACK HARBOUR W/DOCK.
See all 251 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.
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Top things to do in Chester

Image for Fisheries Museum of the Atlantic

Fisheries Museum of the Atlantic

£6
Per adult
Fisheries Museum of the Atlantic
See all activities in Chester

Plan your Chester holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Chester. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation* , because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page. 
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Chester holiday package?
Whether it’s your flight or hotel, you can cancel or alter it. Booked your Chester holiday package in the last 24 hours? You may be able to make changes for free. For bookings made more than 24 hours ago, you may be charged a fee by your hotel, airline or car rental company. For more details, check out our Customer Service Portal. We’ll help you every step of the way.
When is the best time of year to visit Chester?
If you love the excitement that comes with peak season, you’ll enjoy visiting Chester in . If you’re looking for a calmer vibe, will suit you better. Don’t want to spend an arm and a leg? Perhaps avoid , when things like airfares and hotels are more expensive. is generally when you’ll score the best deals.
How far in advance should I book my Chester holiday?
Browse Expedia to compare international fares as soon as you’ve got your travel dates. In many cases, you can purchase a ticket up to a year before departure. If you don’t see your preferred air carrier, or you’ve left things to the last moment, don’t despair. Cheap tickets to Chester occasionally appear just weeks before departure.
What should I know before booking a Chester travel package?
You’ll enjoy big savings when you bundle your flights, hotels and rental cars into a travel package. Not just that, booking everything in one spot just makes things easier. So why waste time or money? Whether you’re putting together a ritzy city getaway or a budget solo adventure, check out our package deals today.
Does Expedia offer Book Now, Pay Later Chester holiday packages?
Thanks to our proud partnership with online lender Affirm, you can choose to Book Now, Pay Later. You can customize your trip with Expedia packages, so why not customize your payment arrangement while you’re at it?