Chester Vacation Packages

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Photo by Rachel Kent

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    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 $739, price is now CA $570 per person
CA $570
per person
Jun 18 - Jun 22
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.2/10 Very Good! (759 reviews)
Over all great for the price

Reviewed on May 8, 2026

Sandman Signature Dartmouth Hotel & Suites

Sandman Signature Dartmouth Hotel & Suites

3 out of 5
Price was CA $1,105, price is now CA $859 per person
CA $859
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.4/10 Exceptional! (2,468 reviews)
Clean Room, Modern Sleek Design.

Reviewed on May 6, 2026

Hampton Inn by Hilton Halifax Downtown

Hampton Inn by Hilton Halifax Downtown

3 out of 5
Downtown Halifax
Price was CA $2,835, price is now CA $2,262 per person
CA $2,262
per person
Jul 11 - Jul 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.6/10 Excellent! (1,192 reviews)
We were able to park the car and walk to so many things! Great location.

Reviewed on May 8, 2026

The Hollis Halifax a DoubleTree Suites by Hilton Hotel

The Hollis Halifax a DoubleTree Suites by Hilton Hotel

4 out of 5
Downtown Halifax
Price was CA $2,388, price is now CA $1,909 per person
CA $1,909
per person
Jul 11 - Jul 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (812 reviews)
One of the female front desk staff was short and made me feel very embarrassed.i think she was if Eastern European decent . Possibly Ukrainian . She processed the wrong credit card for payment without asking me and it was denied. Which I knew it would be because I only have a $500 limit on that card for the purpose of being wrongly charged. It was only to hold the room. Her entire face and attitude changed like I was some kind of criminal. I gave her another card I actually wanted it on for points purposes and it was fine . But her glare and stone face was ridiculous.

Reviewed on May 7, 2026

Claymore inn & Suites

Claymore inn & Suites

4 out of 5
Price was CA $710, price is now CA $579 per person
CA $579
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.2/10 Very Good! (626 reviews)
Clean property, kind staff and excellent customer service

Reviewed on May 8, 2026

Chester Hotel Deals

Spyglass Seasted | Stunning Ocean Views & Coastal Comfort

Spyglass Seasted | Stunning Ocean Views & Coastal Comfort

Chester Basin NS
Get rates
Spyglass Seasted | Stunning Ocean Views & Coastal Comfort
The Lower Deck Ocean Escape /Paddle Boards, Kayaks and Bikes

The Lower Deck Ocean Escape /Paddle Boards, Kayaks and Bikes

East Chester NS
10/10 Exceptional! (16 reviews)
Lower deck
The Lower Deck at East Chester was a delight. The view was amazing, from every window to the deck outside. Everything that you would need for a comfortable stay was available. The couches and beds were amazing, and the day bed was a wonderful reading spot.

Reviewed on Sep 16, 2024

Get rates
The Lower Deck Ocean Escape /Paddle Boards, Kayaks and Bikes
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 $176 per night from May 10 to May 11
CA $176
CA $206 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (2,032 reviews)
Spacious room, clean and comfy beds

Reviewed on May 8, 2026

Future Inns Halifax
See all 581 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 $570, 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.