Chester Islands Vacations from $802

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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.
Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
Price was $978, price is now $802 per person
$802
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
8.6/10 Excellent! (1,009 reviews)
We stayed at this inn for 5 days to explore the Halifax area. The convenient location was the best part. There were a few things that made our stay less enjoyable. The walls are very thin and we could hear noise from the hallway, outdoors and upper rooms. There was lots of noise from other guests in the early morning and late evening. The beds were not comfortable as they were too soft. The linens were old and pilling. They also did not make beds or change linens for the whole stay. The fitness room was closed the whole time and the pool was also closed for part of our stay. The breakfast was not very appealing. It was basically toast and a few small apples. Overall, I would not recommend or stay there again.

Reviewed on May 25, 2026

Hilton Garden Inn Halifax Airport

Hilton Garden Inn Halifax Airport

3 out of 5
Price was $1,097, price is now $897 per person
$897
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
8.6/10 Excellent! (1,457 reviews)
Clean great staff lady at breakfast area was so friendly. We had a great chat.

Reviewed on May 25, 2026

The Lord Nelson Hotel & Suites

The Lord Nelson Hotel & Suites

4.5 out of 5
Downtown Halifax
Price was $1,359, price is now $1,116 per person
$1,116
per person
Aug 13 - Aug 18
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.2/10 Wonderful! (2,170 reviews)
Best seafood chowder soup at the hôtel restaurant. Hôtel well located, close to most interesting attractions.

Reviewed on May 25, 2026

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was $991, price is now $828 per person
$828
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.2/10 Wonderful! (2,125 reviews)
Breakfast was simple ,fresh and easy to navigate

Reviewed on May 24, 2026

Red George Inn and Suites

Red George Inn and Suites

2.5 out of 5
Downtown Halifax
Price was $1,081, price is now $919 per person
$919
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.4/10 Exceptional! (64 reviews)
The location is great!

Reviewed on May 25, 2026

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Chester Islands Hotel Deals

The Homeport Motel

The Homeport Motel

2 out of 5
167 Victoria Road Lunenburg NS
$106 nightly
The price is $121 total per night from May 31 to Jun 1
$121 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (595 reviews)
"Nice property, quiet, clean, comfortable, close to central Lunenburg."

Reviewed on May 25, 2026

The Homeport Motel
Smugglers Cove Inn

Smugglers Cove Inn

4 out of 5
139 Montague Street Lunenburg NS
9/10 Wonderful! (800 reviews)
"great location. the town is too cute. the staff was real friendly, even walked to our car to grab the bags."

Reviewed on May 23, 2026

Get rates
Smugglers Cove Inn
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
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $162 total per night from May 31 to Jun 1
$162 total
May 31 - Jun 1
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Poor quality service with an argumentative clerk at check in. For some reason, my stay was inelegiable for rewards point (first time Ive ever been told this) and her excuse was that these points cost the hotel money therefor not everyone qualifies. I travel to Bridgewater on a regular basis for work ..."

Reviewed on May 25, 2026

Best Western Plus Bridgewater Hotel & Convention Centre
See all 356 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.

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

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Frequently asked questions

How much does a Chester Islands vacation package cost?
Offering great value package deals from $802 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.