Boston Vacations

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  • Better together

    Save up to SARĀ 5,400 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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Find the Best Boston Vacation Packages

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 SARĀ 264 per night from Aug 5 to Aug 6
SARĀ 264
SARĀ 291 total
5 Aug - 6 Aug
includes taxes & fees
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 SARĀ 421 per night from Jul 28 to Jul 29
SARĀ 421
SARĀ 527 total
28 Jul - 29 Jul
includes taxes & fees
9.2/10 Wonderful! (261 reviews)
"Cannot say enough nice things about our stay! The staff were amazing, friendly and very helpful. Daughter and family relocated to the area, weā€™ve stayed at 3 very disappointing hotels in the area before this trip. The Trail is the best all-around property by a miles! They take dogs, too. You will ..."

Reviewed on 16 July 2026

The Trail Hotel
Ramada by Wyndham Elizabethtown

Ramada by Wyndham Elizabethtown

2.5 out of 5
205 Commerce Dr Elizabethtown KY
Fully refundableReserve now, pay when you stay
The price is SARĀ 270 per night from Aug 3 to Aug 4
SARĀ 270
SARĀ 298 total
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"The shampoo and soap were empty when we arrived we called down to the desk and was told house keeping would bring it up shortly. They never did. The next day we called again and receive shampoo and soap at approximately 7:30pm"

Reviewed on 15 July 2026

Ramada by Wyndham Elizabethtown
See all 459 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.