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 Express Louisville Airport Expo Center by IHG
Hayfield Dundee
CA $1,072
per person
Nov 17 - Nov 23
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,007 reviews)
Expedia sucks. Send me emails to view my reservation and it only lets me thru the app which I don’t have and don’t want
Reviewed on Oct 10, 2026
Cottonwood Airport & Expo Hotel Louisville
Shively
CA $1,121
per person
Nov 17 - Nov 23
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,008 reviews)
My daughter and I stayed at the Cottonwood Louisville Hotel for the weekend, and overall we had a nice stay. The hotel was clean, comfortable, and the staff was very nice and welcoming. My only wish was that there were more restaurants within walking distance, but besides that, everything was good. We enjoyed our stay and would consider staying here again.
Reviewed on Oct 7, 2026
Fairfield Inn & Suites by Marriott Louisville Downtown
Downtown Louisville
CA $1,085
per person
Nov 17 - Nov 23
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.4/10 Very good! (1,009 reviews)
I really enjoyed my visit. The staffs was helpful to help me with directions and my next visit will be to go back there.
Reviewed on Oct 10, 2026
Ready to book your vacation to Boston?
Boston Hotel Deals
The Trail Hotel
1875 New Haven Rd Bardstown KY
Fully refundableReserve now, pay when you stay
CA $209
CA $254 total
Oct 25 - Oct 26
includes taxes & fees
9.2/10 Wonderful! (380 reviews)
"I like how the lobby and the bar area was so inviting. We listened to good music Friday and Saturday night. I didn’t like how small the rooms were and that the doors were outside to your room. I did not like how expensive it was to stay there more than our stays in Nashville."
Reviewed on Oct 10, 2026
Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94
1043 Executive Drive Hardin Elizabethtown KY
Fully refundableReserve now, pay when you stay
CA $102
CA $112 total
Nov 11 - Nov 12
includes taxes & fees
8.8/10 Excellent! (1,712 reviews)
"Just as people had said before, it is an excellent property. They go above and beyond to satisfy guests. The pool was really nice, they gave us snack food, and the staff was really great!"
Reviewed on Oct 11, 2026
Distill-Inn
984 Frost Ave Bardstown KY
CA $153
CA $168 total
Oct 25 - Oct 26
includes taxes & fees
9.4/10 Exceptional! (1,615 reviews)
"Cleanest hotel I’ve stayed at. Lights from the parking lot were excessively bright in the room, but staff, amenities and cleanliness were top notch."
Reviewed on Oct 11, 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 $1,072 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.
