Holliston Vacation Packages

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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.
Hotel Providence

Hotel Providence

4 out of 5
Downtown Providence
per person
Sep 17 - Sep 22
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Providence (PVD)
8.6/10 Excellent! (1,000 reviews)
Wonderful boutique hotel. Many originals antique furnishings and paintings throughout hotel. Room was nice size with modern bathrooms and deco style room furnishings. Decent fitness room in basement enough for full workout. Nice breakfast bar included and coffee/tea setup in lobby throughout day. There are homeless in area and throughout city but was never bothered. Very walkable location to stores and eateries. Lovely staff. Will return.

Reviewed on Jul. 22, 2025

Wayfinder Newport

Wayfinder Newport

4 out of 5
per person
Sep 17 - Sep 22
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Providence (PVD)
7.8/10 Good! (849 reviews)
Property was clean, great vibe, cute room, nice pool. I stayed for 2 nights and enjoyed the hotel very much. Staff was extremely helpful, quick to resolve any issues. (The safe was not working. Housekeeping notified Maintenance and the issue was resolved within 20 minutes. Also needed a microwave, and staff brought one to my room within 10 minutes.) The pool area was very clean, with plenty of lounge chairs, towels, attendants for the drink and snack bar. Great atmosphere. I went to the pool a few times and enjoyed it. I had a burger with fries in the dining room. It was delicious. Also had a quick muffin and coffee. Both were great, but the coffee cake muffin was to die for. Would definitely go back.

Reviewed on Jul. 24, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on Jul. 23, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Friendly and professional service and care. Great location to walk to every site you need to get to. Staff especially Will and Howard (door men) always friendly and asked if you needed anything Thanks to the staff you made our first but not our last stay amazing

Reviewed on Jul. 25, 2025

Ready to book your vacation to Holliston?

 

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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
The price is CA $259 per night from Aug 10 to Aug 11
CA $259
CA $302 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,487 reviews)
"Great place. Just be prepared that there is no curb drop off or hotel parking, so figure out how you are going to park and get your suitcases there ahead of time. Very modern, good restaurant/coffee bar and large hangout lobby, 10 min walk to Finway area. Highly recommend."

Reviewed on Jul. 23, 2025

citizenM Boston Back Bay
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
The price is CA $194 per night from Aug 10 to Aug 11
CA $194
CA $226 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (3,782 reviews)
"Great"

Reviewed on Jul. 24, 2025

Copley Square Hotel, a FOUND Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive, Cambridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 10 to Aug 11
CA $185
CA $247 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,020 reviews)
"Nice stay"

Reviewed on Jul. 23, 2025

Hyatt Regency Boston/Cambridge
See all 1,937 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.
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Frequently asked questions

How much does a Holliston vacation package cost?
You can pick up a vacation package to this popular destination from CA $957 on Expedia. But how much your vacation to Holliston costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Holliston?
January, February and November are great times to search for cheap Holliston vacation packages. Choosing to travel in quieter months means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Holliston?
The ideal duration of your Holliston vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to tick off all the top sights and discover some hidden gems along the way.
Is it worth booking a vacation package to Holliston?
From cool attractions such as Pinecrest Golf Club and Pleasure Point to its excellent history, a Holliston vacation delivers big on experiences. With so much to see and do, find out for yourself why Holliston is such a good vacation destination.
How to find the best Holliston package deals?
Use Expedia's filters to help you find some tempting Holliston package deals. When you begin your search, simply 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 score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Holliston vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights separately. Better still, you can tailor your Holliston trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Holliston?
If you're planning a spontaneous Holliston getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Holliston?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Holliston.
  2. Plan your budget wisely: Besides the cost of your accommodations, you'll need to consider other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Holliston.
  3. Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Holliston. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Holliston vacation package that brings all your bookings together.

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