Holliston Vacations from $320

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Price was $456, price is now $320 per person
$320
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (2,117 reviews)
Room was great. Wish I stayed longer. Airport was close by, shuttle at 4am was really nice!

Reviewed on Nov 2, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $944, price is now $552 per person
$552
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.

Reviewed on Oct 13, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $997, price is now $604 per person
$604
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
Excellent hotel, great location, staff fantastic

Reviewed on Oct 31, 2025

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

3 out of 5
Spring Hill
Save 100% on your flight
Price was $939, price is now $627 per person
$627
per person
Dec 27 - Jan 3
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,006 reviews)
updated decor, comfortable and clean

Reviewed on Nov 2, 2025

The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Price was $544, price is now $385 per person
$385
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (1,952 reviews)
Easy check in and nice staff

Reviewed on Nov 3, 2025

Don't see what you're looking for?
See all available trips from Columbus to Holliston
View all trips

Discover the most popular places to visit in Holliston

Pinecrest Golf Club

Enjoy a round of golf in Holliston at Pinecrest Golf Club. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Pinecrest Golf Club

Holliston Hotel Deals

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $162 total per night from Nov 16 to Nov 17
$162 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,967 reviews)
Fine for the price. Good for solo traveler. Central location.

Reviewed on Nov 1, 2025

citizenM Boston Back Bay
The Charles Hotel

The Charles Hotel

4 out of 5
One Bennett Street, Cambridge, MA
Fully refundableReserve now, pay when you stay
$238 nightly
The price is $276 total per night from Nov 23 to Nov 24
$276 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (1,018 reviews)
Super area with lots of cafes and restaurants, close to downtown and key areas to visit, wonderful walking along the river and Harvard campus

Reviewed on Oct 28, 2025

The Charles Hotel
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $137 total per night from Nov 16 to Nov 17
$137 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (3,861 reviews)
Great location

Reviewed on Nov 1, 2025

Copley Square Hotel, a FOUND Hotel
See all 2,014 properties in Holliston
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Holliston vacation package cost?
You can pick up a vacation package to this destination from $320 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

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