Chester Vacation Packages

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  • Better together

    Save up to CA $4,200 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

FlightsFlightsHotelsHotels

Chester

Chester
Point Riche Lighthouse sits at the western tip of the Point Riche peninsula near Port au Choix National Historic Site, overlooking the Gulf of St Lawrence.
FlightsFlightsHotelsHotels

Western Shore

Western Shore

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
Price was CA $1,213, price is now CA $921 per person
CA $921
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.2/10 Very Good! (763 reviews)
Staff was fantastic and breakfast was really good, will stay again when back in area.

Reviewed on May 18, 2026

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
Price was CA $3,414, price is now CA $2,560 per person
CA $2,560
per person
Jul 8 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
10/10 Exceptional! (5 reviews)
Spacious very clean and all the amenitiies

Reviewed on Oct 12, 2025

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was CA $1,642, price is now CA $1,304 per person
CA $1,304
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.2/10 Wonderful! (2,145 reviews)
Clean rooms, extremely friendly staff, and decent location.

Reviewed on Jun 4, 2026

HFX Airport Hotel

HFX Airport Hotel

2.5 out of 5
Price was CA $1,171, price is now CA $945 per person
CA $945
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
8.2/10 Very Good! (4,046 reviews)
It’s aged, but good for a night close to the airport

Reviewed on Jun 4, 2026

Brier Island Lodge

Brier Island Lodge

3 out of 5
Price was CA $1,170, price is now CA $945 per person
CA $945
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.4/10 Very Good! (458 reviews)
Great view of the harbour. Natural setting. Excellent restaurant

Reviewed on May 29, 2026

Chester Hotel Deals

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is CA $205 per night from Jun 14 to Jun 15
CA $205
CA $234 total
Jun 14 - Jun 15
includes taxes & fees
8.2/10 Very Good! (498 reviews)
"We had a lovely stay at the hotel! The view of the ocean from the balcony was beautiful. A bit inconvenient to lug suitcases down steps to our room on the 4th floor but we managed because our cases were not heavy. Conveniently located to Oak Island which was our main reason for the visit. Also very ..."

Reviewed on Jun 5, 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 CA $189 per night from Jun 28 to Jun 29
CA $189
CA $222 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (2,105 reviews)
"Excellent property, great staff, very clean, property had easy access to everything. Very well done!"

Reviewed on Jun 5, 2026

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 CA $152 per night from Jun 15 to Jun 16
CA $152
CA $179 total
Jun 15 - Jun 16
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Beautiful hotel and our room was very clean and up to date! The only complaint I have is the breakfast. The only hot ready item was beans and there were baggies of boiled eggs and pancakes in the fridge. Lots of bread and yogurt if you're not looking for a hot meal"

Reviewed on Jun 2, 2026

Coastal Inn Halifax
See all 586 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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Frequently asked questions

How much does a Chester vacation package cost?
Starting from just CA $921, 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.