Boston Bay 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
Your Boston Bay Vacation
Take the worry out of planning your next big adventure with a Boston Bay vacation package. Whether you're lured here by its art, food, architecture or other highlights, this city offers endless possibilities for fun. Any trip to Boston Bay needs a well-crafted itinerary. Fill yours with leading attractions like Boston Bay Beach, Blue Lagoon and Frenchmans Cove Beach. Expedia will help you escape the everyday. Tailor your vacation to Boston Bay to match your travel style, whatever that may look like.
Top Boston Bay Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $10,252
per person
Nov 16 - Nov 20
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Miami Vacation Rentals - Brickell
Brickell
CA $3,439
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (570 reviews)
The property is under renovation, so no pool. there is also an additional property fee that was not disclosed up front. As a result, I may have chosen another property if I had known the complete price. The property itself is very nice as is the gym, it is also in an excellent location.
Reviewed on Oct 7, 2026
Miami Vacation Rentals - Downtown
Downtown Miami
CA $3,344
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (92 reviews)
Beware! The parking is not as advertised and cost a fortune. The room was noisy at night making sleep difficult due to noisy air conditioner. The staff at the hotel was quite unfriendly and was quite unhelpful. And most of all getting in touch with Expedia was impossible to achieve, even as I write this review they have not responded to my claims.
Reviewed on Oct 4, 2026
Ready to book your vacation to Boston Bay?
Boston Bay Hotel Deals
Private Oasis - Portland’s Coastal Gated Hideaway
Fair Prospect Portland Parish
CA $67
CA $155 total
Oct 11 - Oct 12
includes taxes & fees
10/10 Exceptional! (1 review)
"The listing didn’t really represent this quant hideaway. I grew up in this community so it was great visiting and have this place to decompress and chill. Very cute spot, the host was super, asked if I needed anything at the store and he was very available to assist as needed, I had my ex to assist ..."
Reviewed on Jul 21, 2026
Ahh! (Ocean View Studio with Private Bath)
Boston Bay Portland Parish
CA $105
CA $252 total
Oct 22 - Oct 23
includes taxes & fees
10/10 Exceptional! (2 reviews)
Clean, Great View
"Not the easiest drive up to the place, but the view is magnificent. The place is clean, and the hosts are friendly and helpful. If you're looking for an inexpensive decent studio in Portland with air conditioning, hot water, and a terrific view, consider this place."
Reviewed on Nov 9, 2023
Sea Cliff Resort
Ross Craig Long Bay Portland
Fully refundable
CA $146
CA $184 total
Oct 21 - Oct 22
includes taxes & fees
8/10 Very good! (241 reviews)
"Enjoyed"
Reviewed on Sep 27, 2026
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.
Frequently asked questions
How much does a Boston Bay vacation package cost?
You can grab a vacation package to this top destination from CA $988 on Expedia. However, how much your vacation to Boston Bay costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Boston Bay?
You can generally find lower rates and better availability in January, May and September. Explore our cheap Boston Bay vacation packages and you could get some great off-season discounts.
How many days is enough for Boston Bay?
Typically, a handful of days is enough to tick off the main attractions during your Boston Bay vacation. However, if you want to have some time to rest or take day tours, consider extending your trip.
How to find the best Boston Bay package deals?
Finding a cheap Boston Bay package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Boston Bay package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Boston Bay vacation as a package?
You can enjoy significant savings on your next Boston Bay getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Boston Bay?
If you have your Boston Bay vacation dates confirmed, book early to score some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Boston Bay?
- Choose your dates: What you want to do in Boston Bay and your preferred season can help you decide when to travel.
- Budget wisely: On top of the cost of your accommodations, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Boston Bay.
- Determine how many days away: Start by compiling a list of the sights and activities you want to experience in Boston Bay. Then, estimate how long you'll need for each, including any travel time.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Boston Bay vacation package that brings all your bookings together.
Explore a world of travel with Expedia
- Hotels with Tennis Courts in Portland
- Jamaica Colors Eco
- Villas in Port Antonio
- Fairy Hill Hotels
- Boston Bay Hotels
- 5 Star Hotels in Port Antonio
- Hotel Wedding Venues Hotels in Port Antonio
- Historic Hotels in Port Antonio
- Hotels near Boston Bay Beach
- Teejay's rustic retreat
- Villa Juanita
- Go Natural Jamaica Retreats
- Sea Bell Resort Limited
- Happy Grove Hotels
- Wilks Bay Resort One
- Cheap Hotels in Hope Bay
- Golf Hotels in Portland
- Hotels near Frenchman's Cove Beach
- Long Bay Hotels
- Hordley Hotels
- Titchfield Peninsula Hotels
- Cheap Hotels in Portland
- Hotels near Winnifred Beach
- All Inclusive Resorts and in Portland
- Oceanfront Hotels in Portland
- Resorts in Port Antonio
- Portland Hotels
- Amazing Caribbean Sea & Mountain Views
- Pimento Lodge
- Hotels near Trident Castle
- Port Antonio Hotels
- Sea Cliff Resort
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
