Boston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Boston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
Downtown Louisville
Price was CA $1,298, price is now CA $1,055 per person
CA $1,055
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.4/10 Exceptional! (1,959 reviews)
The hotel was very nice and clean. There was an upscale food court. The pool area was very nice. The hotel was in a great location to Whiskey Row, casino and multiple restaurants and Bars.

Reviewed on Jul 4, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was CA $1,627, price is now CA $1,387 per person
CA $1,387
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.6/10 Exceptional! (476 reviews)
Close to everything and very clean.

Reviewed on Jul 5, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was CA $1,241, price is now CA $1,148 per person
CA $1,148
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Beautiful hotel

Reviewed on Jul 1, 2026

The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was CA $1,210, price is now CA $1,134 per person
CA $1,134
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.4/10 Exceptional! (1,260 reviews)
The Brown is one of our favorite places to stay when downtown Louisville

Reviewed on Jul 4, 2026

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Price was CA $1,121, price is now CA $1,072 per person
CA $1,072
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (4,166 reviews)
Todo estuvo muy bien, probablemente la carpeta de el piso 9 ocupe una buena lavada o ser remplazada por que si despide un olor a humedad

Reviewed on Jul 5, 2026

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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
The price is CA $80 per night from Aug 3 to Aug 4
CA $80
CA $88 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,621 reviews)
"Our stay was great, no problems or complaints. Smooth check in, good complimentary breakfast. Every thing went well, would highly recommend."

Reviewed on Jul 4, 2026

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
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jul 12 to Jul 13
CA $150
CA $189 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (244 reviews)
"It was an extremely beautiful place that’s very well maintained. We look forward to going back and exploring the area again and that will be our place to stay."

Reviewed on Jul 3, 2026

The Trail Hotel
Distill-Inn

Distill-Inn

2.5 out of 5
984 Frost Ave Bardstown KY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jul 9 to Jul 10
CA $175
CA $193 total
Jul 9 - Jul 10
includes taxes & fees
9.4/10 Exceptional! (1,555 reviews)
"What a great place to stay! Great staff and a shout out to Mary#2 for the warm, friendly welcome and suggestions for dinner. Will definitely stay there again. Thanks for making my stay enjoyable!"

Reviewed on Jul 5, 2026

Distill-Inn
See all 458 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?
You can grab a vacation package to this top destination from CA $1,055 on Expedia. But how much your vacation to Boston costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Boston?
You can generally find lower rates and greater availability in January, February and November. Check out our cheap Boston vacation packages and you could land some excellent off-season deals.
How many days is enough for Boston?
With a well-planned itinerary, you can easily visit the main Boston sights in a handful of days. But if you prefer to discover hidden gems or go on day trips, think about booking your Boston vacation for longer.
How to find the best Boston package deals?
Use Expedia's handy filters to help you find some of the best Boston package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Boston package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Boston vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalize your Boston getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Boston?
If you're considering a spur-of-the-moment Boston getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Boston?

  1. Pick your travel dates: What you plan to do in Boston and your favourite season will help you decide when to go.
  2. Set a budget: Consider expenses such as flights, meals and transportation when working out how much to put aside for your trip to Boston. Then, select a property that works with your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. Determine how many days away: Start by listing all the activities and attractions you want to get to in Boston. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Boston vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.