Boston Vacations from $224

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The Latest Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
TownePlace Suites by Marriott Louisville North

TownePlace Suites by Marriott Louisville North

3 out of 5
Price was $306, price is now $224 per person
$224
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
9.2/10 Wonderful! (590 reviews)
The property was clean and located in a very nice neighborhood. However the air conditioner was very loud.

Reviewed on Aug 21, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $489, price is now $325 per person
$325
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Honestly it was awesome, my issue was with expedia they had no record of pre paying or my reservation , they took charge and had it resolved i absolutely am going back and the only place im staying at is there.awesome service

Reviewed on Aug 22, 2025

Fairfield Inn By Marriott Louisville North

Fairfield Inn By Marriott Louisville North

2.5 out of 5
Price was $315, price is now $238 per person
$238
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
8/10 Very Good! (536 reviews)
Property was pleasant. It had a little bit of a smell in hallways. The rooms were clean and a nice area out of the way. Good staff that called me so I could check in early.

Reviewed on Jul 18, 2025

The Bellwether Hotel

The Bellwether Hotel

2 out of 5
Tyler Park
Save 100% on your flight
Price was $515, price is now $389 per person
$389
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
8/10 Very Good! (16 reviews)
The boutique Bellwether Hotel is so beautiful and a step back in time. The art deco design, the second floor lounge, and the rooms all beautifully decorated and comfortable. Walk to restaurants, grocery, bars and antique shops.

Reviewed on Apr 25, 2025

Comfort Inn & Suites Clarksville - Louisville North

Comfort Inn & Suites Clarksville - Louisville North

2.5 out of 5
Price was $317, price is now $240 per person
$240
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
9/10 Wonderful! (968 reviews)
The presidential suite was huge! Definitely will stay again.

Reviewed on Aug 15, 2025

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Boston Hotel Deals

Distill-Inn

Distill-Inn

2.5 out of 5
984 Frost Ave, Bardstown, KY
$93 nightly
The price is $102 total per night from Sep 10 to Sep 11
$102 total
Sep 10 - Sep 11
Total with taxes and fees
9.2/10 Wonderful! (1,295 reviews)
"It was great place to stay if your going on the bourbon trail the theme was great."

Reviewed on Aug 23, 2025

Distill-Inn
Best Western Louisville South / Shepherdsville

Best Western Louisville South / Shepherdsville

2.5 out of 5
362 Brenton Way, Louisville, KY
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $84 total per night from Aug 30 to Aug 31
$84 total
Aug 30 - Aug 31
Total with taxes and fees
8.4/10 Very Good! (833 reviews)
A little ways to go
"They have done remodeling but my first room had sticky residue on bathroom floor. The front desk came to check it out and did change rooms for me. Hopefully it all gets straightened out. On a very positive note it said continental breakfast but there was gravy, biscuits, sausage, eggs, and normal ..."

Reviewed on Aug 24, 2025

Best Western Louisville South / Shepherdsville
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
$79 nightly
The price is $87 total per night from Aug 27 to Aug 28
$87 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (1,402 reviews)
"Very welcoming."

Reviewed on Aug 23, 2025

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94
See all 386 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.

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Frequently asked questions

How much does a Boston vacation package cost?
Offering excellent value package deals from $224 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.