Holliston Vacations from $632

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Your Holliston Vacation

Enjoy unforgettable adventures when you lock in a vacation package to Holliston. Whether you're a foodie, history buff or just a traveler who loves experiencing new places, there's something for everyone in this lively city. Make your trip to Holliston even more fulfilling by going sightseeing. Ashland State Park, Pinecrest Golf Club and Stoddard Park are among the popular attractions you'll want to explore. No matter your travel plans or the size of your budget, putting together a tailored Holliston vacation is a cinch with Expedia.

The Latest Holliston vacation packages

Price found within the past 48 hours. Click for updated prices.
Beachside Village Resort
Boston Harbor Hotel
Meco Hotel - Hostel
Chatham Tides
Wayfinder Newport
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Holliston Hotel Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $196 total per night from Jul 5 to Jul 6
$196 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (2,374 reviews)
"Great location next to the Charles River and only two miles from the center of Boston. My room was excellent. The restaurant had an excellent breakfast and dinner. I wish it had been open for lunch. The little cafe shop did not have much of a selection and no hot food. A bonus was the hotel’s fitness ..."

Reviewed on Jun 21, 2026

Hyatt Regency Boston/Cambridge
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
$162 nightly
The price is $189 total per night from Jun 30 to Jul 1
$189 total
Jun 30 - Jul 1
Total with taxes and fees
8.2/10 Very Good! (490 reviews)
"This property is in a good location however the noise level is too much. All noise from upstairs, next door or people in hallway is disruptive. Unable to get rest. I would not book this hotel nor do I recommend it."

Reviewed on Jun 21, 2026

The Midtown Hotel MOD Collection by Sonesta
Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

4 out of 5
39 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $243 total per night from Jul 5 to Jul 6
$243 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (1,835 reviews)
"My only real complaint is that the room I was in was an adjoining room. The door was paper thin and it was if the people in the next room were at the foot of my bed. The location of hotel was prime and front desk staff exceptional. Highly recommend but avoid an adjoining room if not needed."

Reviewed on Jun 20, 2026

Sheraton Boston, a Marriott Hotel
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 Holliston Vacation Packages

Holliston Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
14,000
Top Sights
Hopkinton State Park, Fun and Games Family Entertainment Center and Ashland State Park

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Frequently asked questions

How much does a Holliston vacation package cost?
You can pick up a vacation package to this destination from $632 on Expedia. But how much your vacation to Holliston costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Holliston?
If you're hoping to snag a cheap Holliston vacation package, consider planning a trip in December, January and February. You'll typically find better prices on flights and accommodations during these months — ideal for budget-conscious travelers.
How many days is enough for Holliston?
The ideal length of your Holliston vacation depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to visit all the leading attractions and discover some hidden gems along the way.
Is it worth booking a vacation package to Holliston?
Boasting a host of highlights starting with its top-notch history, Holliston is a good vacation destination. Whether you'd like to explore sights such as Pinecrest Golf Club and Pleasure Point or venture off the beaten track, you'll find loads to see and do on your Holliston vacation.
How to find the best Holliston package deals?
Use Expedia's filter tool to help you find some great Holliston package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Holliston package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Holliston vacation as a package?
You can enjoy significant savings on your Holliston break by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Holliston?
If you have your Holliston travel dates confirmed, book as soon as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Holliston vacation packages?
Your Holliston break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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