Holliston Vacations from $543
Book a Hotel + Flight or Car together to unlock savings
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.
Boston Lodge and Suites
Dorchester
$543
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 2026
Stay near popular Holliston attractions
Pinecrest Golf Club
6.0/10 (1 review)
This scenic par-66 course features tree-lined fairways and strategic challenges across 5,003 yards of rolling terrain. Practice at the 300-yard driving range before enjoying post-round dining at Anthony's on the Green.
Pleasure Point
6.0/10 (1 review)
Lake Winthrop's serene shoreline offers a peaceful escape for swimming and picnicking. Purchase your day pass in advance to enjoy this local gem's sandy beach and playground facilities.
Stoddard Park
6.0/10 (1 review)
Stoddard Park offers a tranquil sandy beach on Lake Winthrop with playgrounds and sports fields. Families can swim in the clear waters or enjoy picnics under shade trees with charcoal grills available.
Holliston Hotel Deals
The Westin Copley Place, Boston, a Marriott Hotel
10 Huntington Ave Boston MA
Fully refundableReserve now, pay when you stay
$207 nightly
$241 total
Nov 22 - Nov 23
Total with taxes and fees
Arcadian Hotel
1200 Beacon St Brookline MA
Fully refundableReserve now, pay when you stay
$143 nightly
$160 total
Nov 26 - Nov 27
Total with taxes and fees
8.2/10 Very Good! (4,467 reviews)
"K"
Reviewed on Oct 25, 2026
citizenM Boston Back Bay
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
$134 nightly
$156 total
Nov 23 - Nov 24
Total with taxes and fees
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 $543 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.