Holliston Vacations from $561
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
$561
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Luxury Apartments by Hyatus at Boston Everett
$1,398
per person
Oct 15 - Oct 18
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (6 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week.
We did not have a rental car but the parking garage was easily accessible and secure.
We were able to get ubers very easily from the location.
The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient.
The support staff replied to all our messages in the chat option quickly and were very helpful.
The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred.
Would recommend this place without hesitation.
Reviewed on Jun 15, 2026
Good Hotels Boston
South End
$1,317
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.
Reviewed on May 23, 2026
Iris Hotel Boston
Coolidge Corner
$1,261
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (612 reviews)
Staff was amazing to deal with. Room was beautiful. Comfortable bed. Great location. I would recommend.
Reviewed on Aug 6, 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.
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.
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.
Holliston Hotel Deals
The Midtown Hotel MOD Collection by Sonesta
220 Huntington Avenue Boston MA
Fully refundableReserve now, pay when you stay
$171 nightly
$199 total
Aug 16 - Aug 17
Total with taxes and fees
8.2/10 Very Good! (792 reviews)
"The building itself is very old and there is only one elevator that you have to go up a flight of stairs to access. Other than this issue, we were very satisfied with our room. The bed was very comfortable. We never made it down for breakfast any of the days we were there."
Reviewed on Aug 6, 2026
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$189 nightly
$219 total
Aug 30 - Aug 31
Total with taxes and fees
citizenM Boston Back Bay
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
$143 nightly
$167 total
Aug 16 - Aug 17
Total with taxes and fees
9.4/10 Exceptional! (2,972 reviews)
"Had a great stay, rooms are small but very charming and comfortable. Love the huge windows and views. The staff is really friendly and helpful. Great location, with the T right outside the hotel. Perfect for College visits."
Reviewed on Aug 6, 2026
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 $561 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.
Explore a world of travel with Expedia
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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.