Boston Vacations from $695

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
The Trail Hotel

The Trail Hotel

4 out of 5
Price was $858, price is now $695 per person
$695
per person
Jul 10 - Jul 13
just found
Roundtrip non-stop flight included
Philadelphia (PHL) to Louisville (SDF)
9/10 Wonderful! (175 reviews)
This hotel is definitely geared towards people visiting Bardstown to explore the bourbon industry. Neither of us like bourbon but still had a great visit. The hotel is really well done. The food was wonderful and the staff was super friendly. The hotel is only 1 year old so everything is shiny and new.

Reviewed on May 17, 2026

The Reserve on Main

The Reserve on Main

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $6,303, price is now $5,099 per person
$5,099
per person
Jul 9 - Jul 14
found 10 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Louisville (SDF)
9.4/10 Exceptional! (3 reviews)
Super easy! Loved the vibe!

Reviewed on Apr 18, 2026

DuPont Mansion Bed & Breakfast

DuPont Mansion Bed & Breakfast

2 out of 5
Old Louisville
Price was $1,337, price is now $1,086 per person
$1,086
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.6/10 Exceptional! (117 reviews)
No staff was present during the stay. Breakfast didn’t start until 8:30, which was too late for us to wait for. For a bed and breakfast establishment there wasn’t that “feel at home feeling”

Reviewed on May 13, 2026

Central Park Bed & Breakfast

Central Park Bed & Breakfast

3.5 out of 5
Old Louisville
Price was $1,284, price is now $1,045 per person
$1,045
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.2/10 Wonderful! (76 reviews)
Breakfast was different, good. Rm. Rose Garden. Prefer bacon crisp. Love sweet potato soup! Place was clean, noticed debris between coffee table and sofa. Vacuum rug thoroughly. Sofa is old but cushions could be refilled to provide better support.

Reviewed on May 15, 2026

Louisville Bourbon Inn

Louisville Bourbon Inn

5 out of 5
Old Louisville
Price was $1,197, price is now $978 per person
$978
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
10/10 Exceptional! (23 reviews)
The property is beautiful. Our room was lovely—very clean and comfortable. The seating in our room was perfect for reading, and the balcony an extra treat. Allen was so gracious and helpful. The location was great for dinner plans and a short easy drive to Churchill Downs. Breakfast was delicious—especially the biscuits and gravy. And, the young lady that served us breakfast was very nice and helpful. I’d recommend this Bed and Breakfast to anyone who is planning to spend time in Louisville.

Reviewed on May 10, 2026

Don't see what you're looking for?
See all available trips from Columbus to Boston
View all trips

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
$77 nightly
The price is $85 total per night from May 20 to May 21
$85 total
May 20 - May 21
Total with taxes and fees
8.8/10 Excellent! (1,578 reviews)
"They was very kind and the workers"

Reviewed on May 17, 2026

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94
Distill-Inn

Distill-Inn

2.5 out of 5
984 Frost Ave Bardstown KY
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $116 total per night from May 25 to May 26
$116 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,529 reviews)
"Nothing fancy, but very clean and the staff was very friendly. Would stay here again."

Reviewed on May 18, 2026

Distill-Inn
The Trail Hotel

The Trail Hotel

4 out of 5
1875 New Haven Rd Bardstown KY
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $159 total per night from May 25 to May 26
$159 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (194 reviews)
"This hotel is definitely geared towards people visiting Bardstown to explore the bourbon industry. Neither of us like bourbon but still had a great visit. The hotel is really well done. The food was wonderful and the staff was super friendly. The hotel is only 1 year old so everything is shiny and ..."

Reviewed on May 17, 2026

The Trail Hotel
See all 451 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Boston vacation package cost?
Offering excellent value package deals from $695 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.