Holliston Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 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.
Top Holliston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Raffles Boston
Back Bay
Price was CA $2,262, price is now CA $1,270 per person
CA $1,270
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (159 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.
Reviewed on Sep 2, 2025
The Langham, Boston
Downtown Boston
Price was CA $2,709, price is now CA $1,643 per person
CA $1,643
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,011 reviews)
First rate hotel. Definitely a Luxury hotel stay!
Reviewed on Sep 1, 2025
The Charles Hotel
West Cambridge
Price was CA $2,320, price is now CA $1,526 per person
CA $1,526
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
Lou the driver was awesome and very informative. We enjoyed walking to Harvard Yard which is only two blocks away!
So much fun for family’s.
Reviewed on Sep 6, 2025
Holliston Hotel Deals
citizenM Boston Back Bay
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Sep 21 to Sep 22
CA $289
CA $337 total
Sep 21 - Sep 22
includes taxes & fees
Four Points by Sheraton Boston Newton
320 Washington Street, Newton, MA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Sep 21 to Sep 22
CA $169
CA $189 total
Sep 21 - Sep 22
includes taxes & fees
Copley Square Hotel, a FOUND Hotel
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from Sep 21 to Sep 22
CA $242
CA $282 total
Sep 21 - Sep 22
includes taxes & 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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
- Best Hotels in Lowell
- Best Hotels in Nantucket
- Best Hotels in Plymouth
- Best Hotels in Andover
- Best Hotels in Worcester
- Best Hotels in Falmouth
- Best Hotels in Provincetown
- Best Hotels in Mansfield
- Best Hotels in Foxboro
- Best Hotels in Marlborough
- Best Hotels in Lenox
- Best Hotels in Springfield
- Best Hotels in Amherst
- Best Hotels in Hyannis
- Best Hotels in Fall River
- Best Hotels in Rockport
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
