Chester Vacation Packages

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    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top vacation destinations in Chester

Chester which includes a house and a small town or village
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Chester

Chester

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Halifax (YHZ)
8.2/10 Very Good! (692 reviews)
Great views. Wonderful room

Reviewed on Jun. 23, 2025

The Barrington Hotel

The Barrington Hotel

3.5 out of 5
Downtown Halifax
Save 100% on your flight
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
7.8/10 Good! (4,172 reviews)
Elevator wasn’t working properly, our ceiling was crumbling to the ground so we had to move rooms. No compensation was offered but we demanded at least compensation for the parking!

Reviewed on Jun. 28, 2025

Tru By Hilton Yarmouth

Tru By Hilton Yarmouth

2.5 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 18
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
9.4/10 Exceptional! (1,036 reviews)
Just a plain no nonsense place to sleep. The staff was excellent-friendly and helpful. The breakfast was pretty rough. Cold and dry although it was supposed to be hot. Coffee bar frequently out of things. It wasn’t a deal breaker. The room was clean and comfortable.

Reviewed on Jun. 28, 2025

The Sutton Place Hotel Halifax

The Sutton Place Hotel Halifax

5 out of 5
Downtown Halifax
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.6/10 Exceptional! (1,682 reviews)
Check in was simple and enjoyable! Room had a lovely view over downtown where everything is within walking distance. Can't wait to return for a longer stay

Reviewed on Jun. 29, 2025

Future Inns Halifax

Future Inns Halifax

3 out of 5
Clayton Park West
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
9.2/10 Wonderful! (1,665 reviews)
There was nothing I didnt like! It was exactly how pictured and a nice place to stay.

Reviewed on Jun. 29, 2025

Chester Hotel Deals

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Hubbards
The price is CA $180 per night from Jul 7 to Jul 8
CA $180
CA $236 total
Jul 7 - Jul 8
includes taxes & fees
7.8/10 Good! (8 reviews)
Great view
"Great house. Some of the furniture needs changing like the dining room chairs that are very wobbly.3 bedrooms in basement are only doubles so like my son and his wife that are bigger people they had to sleep separately. All in all there was a great view and it was worth the prixe."

Reviewed on Aug. 28, 2024

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
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 retreat
"We had a wonderful time. You can’t beat the views!"

Reviewed on Jun. 19, 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 CA $224 per night from Jun 30 to Jul 1
CA $224
CA $263 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (1,929 reviews)
5 stars
"Very comfortable and clean"

Reviewed on Jun. 28, 2025

Chateau Bedford, Trademark Collection by Wyndham
See all 513 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Starting from just CA $589, a vacation 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 vacation.
What are the top hotels in Chester?
For properties in Deep Cove with cozy 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 vacation?
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 vacation 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 vacation 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.