Boston 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 Boston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Louisville Airport South by IHG
CA $1,336
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,003 reviews)
Todo muy bien y el personal muy atento. La única observación es que tengo es que el último día que nos hospedamos el housekeeping no pasó por nuestra habitación.
Reviewed on Sep 19, 2026
Omni Louisville Hotel
Downtown Louisville
CA $1,455
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9.4/10 Exceptional! (2,106 reviews)
The staff at the Omni Hotel was absolutely wonderful. Everyone was so polite, considerate, and genuinely sympathetic to our family’s situation. They couldn’t have been more accommodating or understanding during a very stressful time. Their kindness and compassion meant so much to us. Thank you for making a difficult situation a little easier!
Reviewed on Sep 17, 2026
Ready to book your vacation to Boston?
Boston Hotel Deals
Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94
1043 Executive Drive Hardin Elizabethtown KY
Fully refundableReserve now, pay when you stay
CA $108
CA $119 total
Oct 20 - Oct 21
includes taxes & fees
Distill-Inn
984 Frost Ave Bardstown KY
Fully refundableReserve now, pay when you stay
CA $157
CA $173 total
Oct 6 - Oct 7
includes taxes & fees
9.4/10 Exceptional! (1,594 reviews)
"From the moment you walk in to the hotel to seeing the room for the first time the cleanness definitely stands out. The staff, it's definitely very accommodating and friendly. Breakfast in the morning is absolutely awesome, and a well stocked bar. I will definitely stay here again when visiting the ..."
Reviewed on Sep 18, 2026
The Trail Hotel
1875 New Haven Rd Bardstown KY
Fully refundableReserve now, pay when you stay
CA $185
CA $227 total
Oct 6 - Oct 7
includes taxes & fees
9.2/10 Wonderful! (333 reviews)
"This was advertised as a HOTEL….. this is MOST DEFINITELY NOT A HOTEL. This is a glorified motel- did not appreciate the accommodation situation, lack of ease to access our room, size of room, layout of room was a typical motel. Did not like at all! This is false advertising when it’s offered as ..."
Reviewed on Sep 18, 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 vacation package cost?
You can grab a vacation package to this top destination from CA $1,194 on Expedia. But how much your vacation to Boston costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Boston?
You can generally find lower rates and greater availability in January, February and November. Check out our cheap Boston vacation packages and you could land some excellent off-season deals.
How many days is enough for Boston?
With a well-planned itinerary, you can easily visit the main Boston sights in a handful of days. But if you prefer to discover hidden gems or go on day trips, think about booking your Boston vacation for longer.
How to find the best Boston package deals?
Use Expedia's handy filters to help you find some of the best Boston package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Boston package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Boston 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 Boston getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Boston?
If you're considering a spur-of-the-moment Boston getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Boston?
- Pick your travel dates: What you plan to do in Boston and your favourite season will help you decide when to go.
- Set a budget: Consider expenses such as flights, meals and transportation when working out how much to put aside for your trip to Boston. Then, select a property that works with your budget, whether that's a wallet-friendly option or a deluxe getaway.
- Determine how many days away: Start by listing all the activities and attractions you want to get to in Boston. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Boston vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
