Chester Islands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.

Top Chester Islands 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
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
8.2/10 Very Good! (714 reviews)
Outstanding and helpful service staff and front desk help that went out of their way to be helpful.

Reviewed on Jul. 30, 2025

The Barrington Hotel

The Barrington Hotel

3.5 out of 5
Downtown Halifax
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
7.8/10 Good! (4,287 reviews)
We had a nice stay at this hotel. It was a bit noisy in the hallway early evening but by midnight we don’t hear anything. The only thing we didn’t like was the parking,it was a bit inconvenient.The parkade was a 2-3 min drive fr.the hotel. But overall it was a good stay. We loved the convenience of this hotel so close to the harbour front where we enjoyed the Buskers performing

Reviewed on Aug. 2, 2025

South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
8.2/10 Very Good! (631 reviews)
Easy to find location, clean!

Reviewed on Aug. 2, 2025

Super 8 by Wyndham Windsor NS

Super 8 by Wyndham Windsor NS

2 out of 5
per person
Oct 14 - Oct 21
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.4/10 Very Good! (1,008 reviews)
Room was very spacious, guest services were great! Pool was Amazing {according to the kids} especially the slide! Breakfast was good. The pancake machine was a hit!!

Reviewed on Jul. 31, 2025

Cambridge Suites Hotel

Cambridge Suites Hotel

3 out of 5
Downtown Halifax
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
9/10 Wonderful! (1,967 reviews)
Great location, easily access to historical sites like public gardens, Halifax Citadel. Walking distance to waterfront.

Reviewed on Aug. 2, 2025

Ready to book your vacation to Chester Islands?

 

Choose your dates

Chester Islands Hotel Deals

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St, Bridgewater, NS
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 4 to Aug 5
CA $185
CA $224 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very Good! (743 reviews)
"Outstanding and helpful service staff and front desk help that went out of their way to be helpful."

Reviewed on Jul. 30, 2025

Travelodge by Wyndham Bridgewater
Miller House By the Bay

Miller House By the Bay

3 out of 5
624 Main street, mahone bay, NS
The price is CA $162 per night from Aug 6 to Aug 7
CA $162
CA $185 total
Aug 6 - Aug 7
includes taxes & fees
9.6/10 Exceptional! (36 reviews)
"We loved EVERYTHING about this place: Margaret, our host, was warm and welcoming. The accommodations were comfortable. Continental breakfast with home-made goodies was a good way to start the day. And Mahone Bay is one of our favourite destinations in Nova Scotia."

Reviewed on Jul. 31, 2025

Miller House By the Bay
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

3.5 out of 5
527 Highway 10 Exit 12, Cookville, NS
The price is CA $238 per night from Aug 24 to Aug 25
CA $238
CA $271 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (920 reviews)
"Josh at front desk was awesome! Super helpful and polite!"

Reviewed on Jul. 29, 2025

Best Western Plus Bridgewater Hotel & Convention Centre
See all 319 properties in Chester Islands
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 Islands vacation package cost?
You'll find cheap prices from CA $367 on Expedia for your Chester Islands break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chester Islands costs.
What are the cheapest months to go to Chester Islands?
You can usually find lower prices and greater availability in January, February and November. Check out our cheap Chester Islands vacation packages and you could score some excellent off-season deals.
How many days is enough for Chester Islands?
You can see all the top attractions in Chester Islands in a few days, including the must-see Tancook Island. If you want an extended Chester Islands vacation, check out what kind of activities and day tours are available nearby.
How to find the best Chester Islands package deals?
Bagging a cheap Chester Islands package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most economical Chester Islands package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chester Islands vacation as a package?
You can enjoy significant savings on your Chester Islands getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chester Islands?
If you've got your Chester Islands vacation dates locked in, book early to grab some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Chester Islands?

  1. Choose your dates: What you plan to do in Chester Islands and your preferred season can help you decide when to go.
  2. Set your budget: Consider costs like flights, meals and transportation when calculating how much to save for your trip to Chester Islands. Then, choose a property that suits your budget, whether that's a wallet-friendly stay or a swankier getaway.
  3. Decide your trip length: Think about how much time you want to spend discovering Chester Islands. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Chester Islands vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.