Boston Vacations from $722
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The Latest Boston vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Louisville Airport Expo Center by IHG
Hayfield Dundee
$722
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (1,010 reviews)
The stay was perfect! I would highly recommend. The people were nice and the breakfast was good.
Reviewed on Aug 17, 2026
Cottonwood Airport & Expo Hotel Louisville
Shively
$1,261
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,013 reviews)
Staff is amazing....the shuttle was not working and we were offered an uber by the front desk mgr. We didn't use, but how nice to be offered an alternative.
Reviewed on Aug 17, 2026
Pillow and Paddock B&B
$1,080
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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
Studio 6 Suites Louisville, KY – Airport/Expo Center
Highland Park
$1,740
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
7.4/10 Good! (714 reviews)
it was a great day great for the money, even though it was next to the airport with the airplane noise, but that was to be expected with it being that close to the airport
Reviewed on Aug 16, 2026
Louisville Marriott Downtown
Downtown Louisville
$962
per person
Oct 15 - Oct 18
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!
Reviewed on Aug 16, 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
$72 nightly
$80 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,663 reviews)
"I would not stay here again. It wasn't very clean , and somewhat outdated in the rooms. The Police were called to the room next to me for a dispute and my children were upset about all of the noise, staff was very nice and helpful"
Reviewed on Aug 16, 2026
Distill-Inn
984 Frost Ave Bardstown KY
Fully refundableReserve now, pay when you stay
$98 nightly
$108 total
Aug 25 - Aug 26
Total with taxes and fees
9.4/10 Exceptional! (1,578 reviews)
"I would stay again. But they have no elevator."
Reviewed on Aug 17, 2026
The Trail Hotel
1875 New Haven Rd Bardstown KY
Fully refundableReserve now, pay when you stay
$135 nightly
$149 total
Aug 25 - Aug 26
Total with taxes and fees
9.2/10 Wonderful! (297 reviews)
"Love the unique style of this particular hotel. Lobby was lovely, rooms were clean and decorated nicely, restaurant was very convenient for breakfast and snacks. Located in Bardstown, driving to & from distilleries was easy. Staff is very accommodating and friendly. We would definitely stay here ..."
Reviewed on Aug 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.
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 $722 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.
