Chester Islands Vacations from $729
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Chester Islands Vacation
Prepare to experience Chester Islands on your own terms with a custom Chester Islands vacation package! Discovering the charms of this interesting city is made simpler with a base in a neighborhood such as Garden Lots, which is great for watersports, among other things. Make your trip to Chester Islands even more fulfilling by going sightseeing. Oak Island, Tancook Island and Chester Golf Club are among the leading attractions worth exploring. Whatever your travel plans or budget, putting together the ultimate tailored Chester Islands vacation is a breeze with Expedia.
The Latest Chester Islands vacation packages
Price found within the past 48 hours. Click for updated prices.
Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse
$1,377
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.8/10 Exceptional! (8 reviews)
Everything was unique especially the automated system. Enjoyed the spa. We had some difficulty using the living room tv. Could not find local channels. Everything was LG channels. Otherwise the location, decor and amenities was extraordinary. We will tell our friends about this wonderful place.
Reviewed on Oct 5, 2026
The Lark & Loon Inn
$1,100
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Halifax (YHZ)
10/10 Exceptional! (156 reviews)
We throughly enjoyed our brief stay at the Lark and Loon. Kevin and Lesley are fantastic hosts. They took fantastic care of us from the start with Kevin providing a warm and informative welcome and the super tasty frittata , fresh bread and berries for breakfast they whipped up and more tips and tricks provided by Kevin.
Our room was spacious and cozy, the bed was super comfortable and the shower was great. They had excellent wifi to boot!
We highly recommend the Lark and Loon if you are staying in Annapolis Royal.
Reviewed on Oct 12, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chester Islands
View all tripsChester Islands Hotel Deals
Bridgewater Hotel
35 High St. Bridgewater NS
Fully refundableReserve now, pay when you stay
$76 nightly
$90 total
Nov 1 - Nov 2
Total with taxes and fees
6/10 (544 reviews)
"Excellent staff"
Reviewed on Oct 12, 2026
Best Western Plus Bridgewater Hotel & Convention Centre
527 Highway 10 Exit 12 Cookville NS
Fully refundableReserve now, pay when you stay
$117 nightly
$133 total
Nov 8 - Nov 9
Total with taxes and fees
Days Inn & Conference Center by Wyndham Bridgewater
50 North Street Bridgewater NS
Fully refundableReserve now, pay when you stay
$104 nightly
$123 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Find the Best Chester Islands Vacation Packages
Chester Islands Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
Top Sights | Bayswater Beach Provincial Park, Chester Playhouse and Lordly House Museum |
More vacations you might like
Frequently asked questions
How much does a Chester Islands vacation package cost?
Offering great value package deals from $729 on Expedia, you'll be thrilled with how little a vacation to Chester Islands costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester Islands?
November, December and January are the best times to look for cheap Chester Islands vacation packages. Choosing to travel in less busy months means you can usually find lower prices on accommodations and flights.
How many days is enough for Chester Islands?
With a well-organized schedule, you can easily visit the most popular Chester Islands attractions in a few days. But if you prefer to discover hidden spots or take day trips, consider booking your Chester Islands vacation for longer.
How to find the best Chester Islands package deals?
Begin your search for a Chester Islands package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Chester Islands package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester Islands getaway off to a flying start.
Is it cheaper to book a Chester Islands vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalize your Chester Islands getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chester Islands?
If you've got your Chester Islands vacation dates confirmed, book as soon as you can to snap up some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Chester Islands vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Chester Islands break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
