Boston Vacations

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Find the Best Boston Vacation Packages

Boston Hotel Deals

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 AEDĀ 464 per night from Nov 24 to Nov 25
AEDĀ 464
AEDĀ 572 total
24 Nov - 25 Nov
includes taxes & fees
The Trail Hotel
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 AEDĀ 217 per night from Dec 12 to Dec 13
AEDĀ 217
AEDĀ 246 total
12 Dec - 13 Dec
includes taxes & fees
8.8/10 Excellent! (1,725 reviews)
"Expedia advertises at Pets Stay Free. That should be changed cause it cost me $30 for one dog. Which is not a big deal. Itā€™s worth and still cheap ā€¦ but wasnā€™t expecting. SUPER CLEAN ROOMS. they smelled so good. Doors from the outside to inside donā€™t always lock or latch on their own. No problem. ..."

Reviewed on 11 November 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
The price is AEDĀ 415 per night from Nov 15 to Nov 16
AEDĀ 415
AEDĀ 458 total
15 Nov - 16 Nov
includes taxes & fees
9.4/10 Exceptional! (1,661 reviews)
"The place has been remodeled with new owners now and is no longer affiliated with Choice Hotels. Bathrooms have been remodeled and the fan in the bathroom works with a nice shower-head too. Everything is decorated in Bourbon showing the history of it and pictures all around of distilleries in the ..."

Reviewed on 10 November 2026

Distill-Inn
See all 483 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.

Frequently asked questions

How much does a Boston vacation package cost?
You can grab a vacation package to this top destination 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 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 favorite 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.