Boston Vacations from $442

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The Latest Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Jeffersonville Louisville North

Hilton Garden Inn Jeffersonville Louisville North

3 out of 5
Price was $529, price is now $442 per person
$442
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (378 reviews)
The stay was excellent starting from the moment we arrived. Jacob welcomed us right away to check us in and tell us all about the property. The hotel is spotless and the room was well designed.

Reviewed on Nov 27, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $731, price is now $543 per person
$543
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,005 reviews)
Loved big screen tv and the beds were very comgortable.

Reviewed on Nov 24, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $708, price is now $526 per person
$526
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
I like the shower and that it had a place to prop your foot while shaving. It was great having an empty fridge where I could store leftovers. I liked the layout of the room and there was plenty of charging plugs. On top of all of that the location was pretty great.

Reviewed on Nov 19, 2025

Hyatt House Louisville East

Hyatt House Louisville East

2 out of 5
Price was $561, price is now $454 per person
$454
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (1,001 reviews)
Very clean courteous

Reviewed on Nov 26, 2025

Aloft Louisville Downtown

Aloft Louisville Downtown

3 out of 5
Downtown Louisville
Price was $592, price is now $496 per person
$496
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Great room and location.

Reviewed on Nov 21, 2025

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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
$70 nightly
The price is $77 total per night from Nov 28 to Nov 29
$77 total
Nov 28 - Nov 29
Total with taxes and fees
8.8/10 Excellent! (1,429 reviews)
The breakfast was really good, love scrambled eggs with sausage and gravy 💯

Reviewed on Nov 23, 2025

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94
The Trail Hotel

The Trail Hotel

4 out of 5
1875 New Haven Rd Bardstown KY
$140 nightly
The price is $155 total per night from Dec 22 to Dec 23
$155 total
Dec 22 - Dec 23
Total with taxes and fees
8.6/10 Excellent! (96 reviews)
The Trail Hotel was a gem, newly remodeled with all the amenities. The staff was hospitable, just sad I didn't bring my suit to sit in the hot tub! We plan to stay again when we revisit The Bourbon Trail.

Reviewed on Nov 23, 2025

The Trail Hotel
Distill-Inn

Distill-Inn

2.5 out of 5
984 Frost Ave Bardstown KY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $112 total per night from Dec 14 to Dec 15
$112 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (1,395 reviews)
Clean and nice hosts

Reviewed on Nov 26, 2025

Distill-Inn
See all 421 properties in Boston
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 $442 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.