Boston Vacations from $607
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The Latest Boston vacation packages
Price found within the past 48 hours. Click for updated prices.
Pillow and Paddock B&B
$978
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
Hyatt Regency Louisville
Downtown Louisville
$698
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,007 reviews)
Gorgeous atrium style hotel just steps away from convention center. Lots to do and see near hotel.
Reviewed on Oct 1, 2026
Crowne Plaza Louisville Airport Expo Ctr by IHG
Fairgrounds
$661
per person
Dec 10 - Dec 14
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,859 reviews)
Excellent staff and service, Love having a restaurant in house, especially with none located nearby.
Reviewed on Oct 2, 2026
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
$68 nightly
$75 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,706 reviews)
"Best motel for the price. Beautiful indoor pool area and whirlpool bath/shower in room. Only issue was privacy blind on windows didn't cover so I had to improvise. Would repeat."
Reviewed on Oct 2, 2026
Distill-Inn
984 Frost Ave Bardstown KY
Fully refundableReserve now, pay when you stay
$106 nightly
$117 total
Oct 4 - Oct 5
Total with taxes and fees
9.4/10 Exceptional! (1,604 reviews)
"We really enjoyed our stay. The staff was amazing, especially Mary."
Reviewed on Oct 2, 2026
The Trail Hotel
1875 New Haven Rd Bardstown KY
Fully refundableReserve now, pay when you stay
$154 nightly
$169 total
Oct 25 - Oct 26
Total with taxes and fees
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 Vacation Packages
Boston Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Louisville Intl. Airport (SDF) |
Population | 270 |
Top Sights | My Old Kentucky Home State Park, Bourbon Heritage Center and The Abbey of Gethsemani |
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Frequently asked questions
How much does a Boston vacation package cost?
Offering excellent value package deals from $607 on Expedia, you'll be pleasantly surprised at how much a vacation to Boston costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Boston?
If you're hoping to book a cheap Boston vacation package, consider planning a trip in August, October and December. You're likely to find lower rates on flights and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Boston?
With a well-organized travel plan, you can easily visit the top Boston attractions in a few days. But if you want to discover hidden gems or go on day tours, consider booking your Boston vacation for longer.
How to find the best Boston package deals?
Begin your search for a Boston package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Boston package deal straight 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 escape off to a flying start.
Is it cheaper to book a Boston vacation as a package?
You can enjoy significant savings on your Boston break by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Boston?
If you've got your Boston travel dates finalized, book as soon as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Boston vacation packages?
Jet off on your dream trip to Boston with help from Expedia's Book Now, Pay Later vacations. No need to save up or hold off until your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
