Boston Bay Vacations from $204

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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.
Masquerade Tower at Rio Hotel & Casino

Masquerade Tower at Rio Hotel & Casino

3 out of 5
Save 100% on your flight
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
7.2/10 Good! (254 reviews)
Good place can’t wait to book again

Reviewed on Aug 3, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1 review)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
per person
Oct 18 - Oct 24
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
5.8/10 (303 reviews)
It was great for beach access. Nothing in our room worked. Coffee pot was broke. Stove was broke. We had to switch on and off the breakers to use it. Toilet would tflush half the time.

Reviewed on Jun 21, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
A Perfect Stay on Ocean Drive I had a wonderful stay at this hotel right on Ocean Drive in South Beach. The location is unbeatable—just steps from the beach and in the heart of all the action. The customer service was attentive and friendly, always ready to help with a smile. The on-site restaurant was a pleasant surprise—great food, good vibes, and drinks. The decor throughout the hotel is stylish and inviting, with that classic South Beach charm. Highly recommend for anyone looking to soak up the Miami vibe in comfort and style!

Reviewed on Jul 31, 2025

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.2/10 Very Good! (800 reviews)
friendly staff, clean rooms, 1 block away from the beach

Reviewed on Jul 22, 2025

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Boston Bay Hotel Deals

Rasta Villa B&B

Rasta Villa B&B

Fair Prospect
$202 nightly
The price is $202 total per night from Aug 4 to Aug 5
$202 total
Aug 4 - Aug 5
Total includes taxes and fees
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

Rasta Villa B&B
Boston Bay, Portland Cozy Corner

Boston Bay, Portland Cozy Corner

Boston Bay
$387 nightly
The price is $387 total per night from Aug 5 to Aug 6
$387 total
Aug 5 - Aug 6
Total includes taxes and fees
Boston Bay, Portland Cozy Corner
Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig, Long Bay, Portland
Fully refundable
$122 nightly
The price is $134 total per night from Aug 11 to Aug 12
$134 total
Aug 11 - Aug 12
Total includes taxes and fees
8/10 Very Good! (148 reviews)
"I recently booked several rooms over the past weekend as my family traveled to Jamaica for a funeral. We had a few mishaps on our part, but the staff was incredibly understanding and accommodating throughout. The rooms were clean, the staff was friendly, and Terrence went above and beyond to make ..."

Reviewed on Jul 22, 2025

Sea Cliff Resort
See all 267 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.

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Frequently asked questions

How much does a Boston Bay vacation package cost?
Offering excellent value package deals from $204 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.