Boston Bay Vacations from $397

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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.

The Latest Boston Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Rio Hotel & Casino, a Destination by Hyatt Hotel

Rio Hotel & Casino, a Destination by Hyatt Hotel

4 out of 5
Save 100% on your flight
Price was $923, price is now $397 per person
$397
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Las Vegas (LAS)
7.8/10 Good! (6,684 reviews)
Beautiful room, very clean, nice staff, great food

Reviewed on Jan 11, 2026

Hotel Alameda Highline

Hotel Alameda Highline

4.5 out of 5
Manhattan
Price was $1,504, price is now $456 per person
$456
per person
Mar 24 - Mar 27
found 18 hours ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
7.6/10 Good! (793 reviews)
No frills but good location and meets all the needs.

Reviewed on Jan 4, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,540, price is now $629 per person
$629
per person
Mar 29 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Staff good Room with problems: toilet, safe vault, tv, no closet, no chair, too small

Reviewed on Jan 6, 2026

Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Price was $1,661, price is now $714 per person
$714
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
Our two bedroom apartment was very comfortable and quiet. We enjoyed our stay very much.

Reviewed on Dec 30, 2025

Beach Park Hotel

Beach Park Hotel

3 out of 5
South Beach
Save 100% on your flight
Price was $1,187, price is now $521 per person
$521
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
6.6/10 (1,001 reviews)
It was in a great spot but hard to get to because ocean st and was closed for the holidays. They say there is parking but you have to go to Colin’s street and it was 40 dollars a night. The room looked a lot shabbier than the picture and the bathroom walls can use a good cleaning

Reviewed on Jan 9, 2026

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Boston Bay Hotel Deals

Rasta Villa B&B

Rasta Villa B&B

Fair Prospect Portland Parish
6/10 (1 review)
Nice property and place to stay with few little exceptions
The property is beautiful. You are on a hill top so you have a nice view to see the Ocean from a distance. bigga owner was great, very friendly and accommodating. There is area for cooking. The rooms are nice and big. The only thing i have to say that isnt good is that my room and a few of the other ...

Reviewed on May 12, 2025

Get rates
Rasta Villa B&B
Ahh! (Pool/Ocean View Room w/ Private Bath)

Ahh! (Pool/Ocean View Room w/ Private Bath)

Boston Bay Portland Parish
$153 nightly
The price is $153 total per night from Feb 1 to Feb 2
$153 total
Feb 1 - Feb 2
Total with taxes and fees
Ahh! (Pool/Ocean View Room w/ Private Bath)
Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Fully refundable
$136 nightly
The price is $149 total per night from Jan 13 to Jan 14
$149 total
Jan 13 - Jan 14
Total with taxes and fees
8/10 Very Good! (168 reviews)
My family and I had a wonderful stay at Sea Cliff Resort. From the moment we arrived, the manager, owner, and his son were warm, hospitable, and assisted us with everything we needed. Their kindness really made our stay feel special.Thank you were we all amazing, The ambiance is peaceful, and the ...

Reviewed on Dec 9, 2025

Sea Cliff Resort
See all 274 properties in Boston Bay
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 Boston Bay Vacation Packages

Boston Bay Essential Information

Language
English
Currency
Jamaican dollars
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Frenchmans Cove Beach, Trident Castle and Boston Bay Beach

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Frequently asked questions

How much does a Boston Bay vacation package cost?
Offering excellent value package deals from $397 on Expedia, you'll be surprised at how little a vacation to Boston Bay costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Boston Bay?
If you're looking to book a cheap Boston Bay vacation package, consider planning a trip in September, November and December. You'll generally find better rates on hotels and flights during these months — perfect for a budget-friendly break.
How many days is enough for Boston Bay?
The ideal length of your Boston Bay vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to hit all the major sights and discover some hidden spots along the way.
How to find the best Boston Bay package deals?
Begin your search for a Boston Bay package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Boston Bay package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Boston Bay adventure underway.
Is it cheaper to book a Boston Bay vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Boston Bay getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Boston Bay?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Boston Bay escape.
How to plan a trip to Boston Bay?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the activities available will also help you decide when to vacation in Boston Bay.
  2. Set a budget: Factor in expenses like transportation, flights and meals when working out how much to set aside for your trip to Boston Bay. Then, select a property that fits your budget, whether that's an economical option or a swankier getaway.
  3. Organize your Boston Bay getaway with Expedia's trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Boston Bay together.
  4. Decide your trip length: Consider how much time you'd like to spend exploring Boston Bay. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Boston Bay vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Have a look at our dedicated travel guide to find some fun things to do in Boston Bay. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Boston Bay vacation packages?
Your Boston Bay trip is meant to be an escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.