Boston Vacations from $398

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The Latest Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Louisville Airport Expo Ctr by IHG
Louisville Marriott Downtown
Holiday Inn Louisville Airport South by IHG
The Villas at French Lick Springs
Hilton Garden Inn Louisville Mall of St. Matthews
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Boston Hotel Deals

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

2 out of 5
1043 Executive Drive Hardin Elizabethtown KY
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Jan 18 to Jan 19
$80 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (1,488 reviews)
Could use more verity on buffet

Reviewed on Jan 9, 2026

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94
Tru by Hilton Shepherdsville Louisville South

Tru by Hilton Shepherdsville Louisville South

2.5 out of 5
191 Centre Drive Louisville KY
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $100 total per night from Jan 24 to Jan 25
$100 total
Jan 24 - Jan 25
Total with taxes and fees
9.2/10 Wonderful! (854 reviews)
Clean room friendly staff

Reviewed on Jan 11, 2026

Tru by Hilton Shepherdsville Louisville South
La Quinta Inn & Suites by Wyndham Bardstown

La Quinta Inn & Suites by Wyndham Bardstown

3 out of 5
3305 East John Rowan Blvd Bardstown KY
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $95 total per night from Jan 25 to Jan 26
$95 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (1,009 reviews)
Nice and clean with friendly helpful staff. Good basic breakfast.

Reviewed on Jan 8, 2026

La Quinta Inn & Suites by Wyndham Bardstown
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 $398 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.