Holliston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    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.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Jul. 26 - Jul. 30
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.2/10 Very Good! (1,662 reviews)
Room was clean and well appointed. Staff was courteous. Fine for our short stay (1 night) but room was extremely small.

Reviewed on May 11, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (269 reviews)
Great property great service

Reviewed on May 5, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (31 reviews)
My stay was lovely. In ordering a cheese plate to await my arrival, a friend alerted the staff that it was my birthday. When I entered my very handsome room, a gorgeous little chocolate bday cake, under domed glass, sat waiting for me. Otherwise, the staff was incredibly attentive, the speakeasy was fun for a delicious cocktail, and the overall atmosphere was one of restrained indulgence. The place doesn’t feel ostentatious. Its elegance was much more understated. I loved it

Reviewed on Apr. 28, 2024

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
Jul. 24 - Jul. 28
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
7/10 Good! (83 reviews)
It was very important that I called a week ahead to pay for parking and to make sure a lockbox was ready for us when we arrived after midnight when no one was at the main desk. I had to call again before we got on the plane for our lock box code. It was close to the subway entrance. The pool was in a different building and it was closed for maintenance. The main reason I picked this location was the pool for our son, he was very disappointed.

Reviewed on Apr. 23, 2024

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
per person
Jul. 24 - Jul. 28
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
8.6/10 Excellent! (1,479 reviews)
Pleasant place. Housekeeping was excellent and flexible. Lovely location.

Reviewed on May 15, 2024

Holliston Hotel Deals

Four Points by Sheraton Boston Newton
Four Points by Sheraton Boston Newton
3.5 out of 5
320 Washington Street, Newton, MA
The price is CA $172 per night from May 27 to May 28
CA $172
CA $193 total
includes taxes & fees
May 27 - May 28
8/10 Very Good! (2,035 reviews)
Room temperature not comfortable
"Room was very hot, despite our thermostat being set to 60 degrees AC. Smelled like someone smoked in the room prior to us."

Reviewed on May 14, 2024

Four Points by Sheraton Boston Newton
Copley Square Hotel
Copley Square Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from May 27 to May 28
CA $251
CA $293 total
includes taxes & fees
May 27 - May 28
8.4/10 Very Good! (2,271 reviews)
"Very convenient location, clean rooms and friendly staff. I will definitely come back!"

Reviewed on May 13, 2024

Copley Square Hotel
The Westin Copley Place, Boston, a Marriott Hotel
The Westin Copley Place, Boston, a Marriott Hotel
4 out of 5
10 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from May 24 to May 25
CA $318
CA $412 total
includes taxes & fees
May 24 - May 25
9/10 Wonderful! (1,007 reviews)
"Super convenient place to stay in the Back Bay. Nice large rooms."

Reviewed on May 13, 2024

The Westin Copley Place, Boston, a Marriott Hotel
See all 1,677 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Holliston vacation package cost?
Get set to book, because a getaway to Holliston starts from an affordable CA $1,010. When you combine your hotels, flights and car rentals into a package, you’ll walk away with the best bargains.
How do I get a cheap travel package to Holliston?
Our Holliston vacation packages offer plenty of savings for the savvy explorer. For the best deal, simply combine your flights, hotels and tours into one neat package. But low prices are only the start of your next awesome adventure. Book with Expedia and you’ll have more than 550 air carriers and 1,000,000 hotels worldwide to pick from. Whatever your budget or style, there’s a package that’s perfect for you.
Where should I stay in Holliston?
A trip to Holliston isn’t complete without visiting Pinecrest Golf Club, Pleasure Point and Stoddard Park. Stay near these popular sights and make sightseeing a breeze.
How far in advance should I book my Holliston vacation?
Travelers can normally look up international airfares on Expedia within 12 months of the departure date. Booking at the last minute? With a bit of luck, it’s still possible to score a cheaper ticket only weeks before your journey.
What does an Expedia Holliston travel package include?
That depends on what you’re looking for. If you’re traveling alone, you might decide to bundle flights and hotels. Taking the whole crew to Holliston? A travel package that includes hotels, rental cars and flights might be a better fit. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Holliston travel package?
You can save a tidy sum by bundling your flights, hotels and rental cars. Once you’ve created your package, you can add on things like day tours or experiences. Your next awesome vacation is only a few clicks away.
Can I choose my airline with a Holliston Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Holliston vacation package?
Because we understand life is full of surprises, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you’ve made your booking in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Holliston

Image for Pinecrest Golf Club

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
Image for Pleasure Point

Pleasure Point

Why not spend a lazy afternoon at Pleasure Point during your trip to Holliston? Wander the lakeside and beaches while you're in the area.

Pleasure Point
Image for Stoddard Park

Stoddard Park

Why not spend a lazy afternoon at Stoddard Park during your trip to Holliston? Wander the lakeside and beaches while you're in the area.

Stoddard Park

Other vacations you might like

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