Five Islands Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Top Five Islands vacation deals
- Bridgetown Motor Inn
Sept 11 - Sept 16Bridgetown Motor Inn + Flight
Bridgetown5 nights2.0 star property7.4/10 - Good (232 reviews)"The staff was extremely helpful. Sandra helped us with the television (Roku). There is a washer and dryer in the facility for free. This hotel had the best breakfast of our trip. There were lots of choices on the buffet. Bridgetown is very small. There are only a few restaurants and they all close early."Reviewed August 6, 2026Roundtrip • Toronto (YTO) - Halifax (YHZ)YYZ - YHZ • Nonstop YHZ - YYZ • NonstopCA $714CA $566found 23 hours agoper traveller - Sandman Signature Dartmouth Hotel & Suites
Sept 18 - Sept 22Sandman Signature Dartmouth Hotel & Suites + Flight
Dartmouth4 nights3.0 star property9.4/10 - Exceptional (2,721 reviews)Roundtrip • Hamilton (YHM) - Halifax (YHZ)YHM - YHZ • 1 stop YHZ - YHM • 1 stopCA $1,062CA $795found 1 day agoper traveller - Coastal Inn Halifax
Sept 18 - Sept 22Coastal Inn Halifax + Flight
Halifax4 nights3.0 star property8.6/10 - Excellent (1,019 reviews)"A good place to stay overnight. BUT... The room doesn't have air conditioning, and the breakfast is meager."Reviewed August 6, 2026Roundtrip • Hamilton (YHM) - Halifax (YHZ)YHM - YHZ • 1 stop YHZ - YHM • 1 stopCA $986CA $747found 1 day agoper traveller - Kennedy House
Oct 8 - Oct 12Kennedy House + Flight
St. Andrews4 nights3.0 star property9.0/10 - Wonderful (1,006 reviews)"Lovely historic building, right in the middle of the main square. Can walk to anything needed. Room was spacious and clean. The bed was a little tired with a saggy mattress, but overall everything was fine. A/c was a window unit but cooled very well. We enjoyed our stay."Reviewed August 6, 2026Roundtrip • Hamilton (YHM) - Saint John (YSJ)YHM - YQM • 1 stop YQM - YHM • 1 stopCA $796CA $619found 11 hours agoper traveller - The Hotel on Pownal
Sept 8 - Sept 13The Hotel on Pownal + Flight
Downtown Charlottetown5 nights2.5 star property8.8/10 - Excellent (1,010 reviews)"Staff were very kind. Our flight was terribly delayed and arrived Hotel at 2AM(!), but Staff waited us and checked in. Also staff at breakfast was friendly and breakfast was good. Our kids loved them. I strongly recommend Hotel Pownal."Reviewed August 6, 2026Roundtrip • Hamilton (YHM) - Charlottetown (YYG)YHM - YYG • 1 stop YYG - YHM • 1 stopCA $1,952CA $1,525found 1 day agoper traveller
Five Islands Hotel Deals
"Fantastic hospitality. My wife and I were amazed at the hospitality we experienced at the Parrsboro Mansion Inn. The proprietors were incredibly helpful in planning activities, offered a great experience and cooked homemade breakfast. This included a gluten free meal for my wife. I strongly recommend! We will be back"
Evangeline's Tower Bed & Breakfast
Evangeline's Tower Bed & Breakfast"Clean and comfortable room in a charming Victorian house with a lot of character. Excellent home-cooked breakfast. If you’re lucky, your hostess, a trained opera singer, will sing for you."
The Sunshine Inn
The Sunshine Inn"Friendly staff easy check in location great"
Frequently Asked Questions
How much does a Five Islands vacation package cost?
Offering great value package deals from CA $566 on Expedia, you'll be pleasantly surprised at how much a vacation to Five Islands costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Five Islands?
You can generally find reduced prices and better availability in January, February and November. Browse our cheap Five Islands vacation packages and you could get some excellent off-season deals.
How many days is enough for Five Islands?
Usually, a handful of days is enough to explore the major sights during your Five Islands vacation. However, if you want to have more time to kick back or take day tours, think about extending your itinerary.
How to find the best Five Islands package deals?
Finding a cheap Five Islands package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Five Islands package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Five Islands vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can tailor your Five Islands escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Five Islands?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Five Islands escape.
How to plan a trip to Five Islands?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Five Islands.
- Budget wisely: Besides the cost of your accommodations, you'll need to factor in other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Five Islands.
- Decide your trip length: Think about how long you want to spend discovering Five Islands. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, lock in the right Five Islands vacation package for you.