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.
Pleasant View Inn

Pleasant View Inn

3 out of 5
Price was CA $2,663, price is now CA $1,792 per person
CA $1,792
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Providence (PVD)
8.2/10 Very good! (1,004 reviews)
I liked that the property was right by the beach, having the beach out the back door was awesome. I liked the resturaunt in the hotel. The prices for drinks and snacks were very expensive, a short walk down the street offered much more affordable shopping. Ther was coffee and water, but no continental breakfast, and a very limited amount of hot cholcolate for the kids, if they weren't up early, they missed out. Also, the game room was not what we expected from the online discription, probably good for children under ten, but my grandchildren were disappointed.

Reviewed on Jul 4, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $4,992, price is now CA $3,130 per person
CA $3,130
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (716 reviews)
Chatham Tides is a slice of heaven. Beautiful location. Clean, well maintained. Staff was super helpful with local restaurants. My wife and I gave it a 11/10

Reviewed on Jul 2, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,267, price is now CA $2,095 per person
CA $2,095
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $5,034, price is now CA $3,335 per person
CA $3,335
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (430 reviews)
Terrible experience. Family of five with three youngsters. Despite being loyal to the MO brand for years, this Boston property is by far one of the worst we have stayed at. To start, there were blood stains on the room carpet. Two rooms on the same floor were confirmed by staff when the booking was made, yet they were not available at check-in. Room service trays sat outside of rooms for hours without being collected. The bathroom was outdated, and the air conditioning was noisy. Overall, the property looked more like a Holiday Inn than a Mandarin Oriental. We will never come back.

Reviewed on Jun 30, 2026

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Price was CA $3,229, price is now CA $2,140 per person
CA $2,140
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
7.8/10 Good! (326 reviews)
convenient short drive from Boston with less traffic over Bourne Bridge. great location with pristine calm and warm water beach. great staff helping get settled on the beach with chairs and umbrella. fortunate to select room with patio first floor which was convenient. rooms were fine nothing scary or amazing. service at bar was quick. food services were slow and basic. great value

Reviewed on Jul 4, 2026

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Holliston Hotel Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is CA $226 per night from Aug 2 to Aug 3
CA $226
CA $305 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,409 reviews)
"Very nice hotel. Staff was terrific. Paperback Restaurant very good."

Reviewed on Jul 3, 2026

Hyatt Regency Boston/Cambridge
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Jul 26 to Jul 27
CA $254
CA $296 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (553 reviews)
"The hotel AC was not working, the room that we booked and even after we changed the room , nothing was working for us . It was so hot , we can’t even sleep properly. This hotel should work on their AC cooling system."

Reviewed on Jul 4, 2026

The Midtown Hotel MOD Collection by Sonesta
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 $267 per night from Jul 26 to Jul 27
CA $267
CA $311 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (2,829 reviews)
"This place was clean and middle of the shopping centers. Good spots for taking the train in three steps and it takes you everybody. Love the atmosphere. Everything was excellent!"

Reviewed on Jul 4, 2026

citizenM Boston Back Bay
See all 2,224 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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Stay near popular Holliston attractions

Pinecrest Golf Club

6.0/10 (1 review)
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.
See properties

Frequently asked questions

How much does a Holliston vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,792 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.

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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.