Holliston Holidays

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Top Flight + Hotel Deals in Holliston

Price found within the past 48 hours. Click for updated prices.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was €998, price is now €765 per person
€765
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
7.8/10 Good! (560 reviews)
Neat and convenient place for a good value.

Reviewed on 1 Jul 2026

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was €2,994, price is now €2,018 per person
€2,018
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
7.8/10 Good! (326 reviews)
Was looking for pet friendly on the beach for a long weekend on the Cape. I hadn’t been to SeaCrest in over a decade. Property was in great shape and looked like it was recently renovated. Fireplace studio was great with a view of Old Silver Beach. Beach service was quick and efficient. There were several events on the property and noise was never an issue. Meals were great. I wish the pizza place was open!

Reviewed on 28 Jun 2026

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was €1,664, price is now €1,238 per person
€1,238
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (179 reviews)
We had an amazing stay! Lots of great activities to entertain our 2 year old!

Reviewed on 28 Jun 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was €1,230, price is now €933 per person
€933
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
Loved it here! Everyone was friendly and helpful.

Reviewed on 1 Jul 2026

Bluebird Dennisport

Bluebird Dennisport

3 out of 5
Price was €1,285, price is now €1,007 per person
€1,007
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.4/10 Very good! (222 reviews)
I would not recommend this property. Unfortunately, our experience was very disappointing. The staff were not particularly welcoming, and we found a cockroach in the bathroom. The TV in our room did not work, there was trash left under the bed, suggesting the room had not been properly cleaned, and we found hair in the shower upon arrival. Additionally, the peel-and-stick wallpaper was coming off the walls, making the room feel poorly maintained. Overall, the cleanliness and upkeep of the property fell well below expectations. Save yourself the hassle and consider staying elsewhere.

Reviewed on 28 Jun 2026

Top hotels in Holliston

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 €180 per night from 2 Jul to 3 Jul
€180
2 Jul - 3 Jul
includes taxes & fees
9/10 Wonderful! (2,396 reviews)
"The staff was hilarious! Multiple staff members made me genuinely laugh. They were helpful and friendly. I also liked the location a lot."

Reviewed on 1 Jul 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 €183 per night from 5 Jul to 6 Jul
€183
5 Jul - 6 Jul
includes taxes & fees
8.2/10 Very good! (540 reviews)
"Parking lot available but did not cater to larger vehicles. Otherwise, service was ok for the short stay."

Reviewed on 1 Jul 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 €162 per night from 5 Jul to 6 Jul
€162
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (2,818 reviews)
"Amazing location"

Reviewed on 30 Jun 2026

citizenM Boston Back Bay
See all 2,226 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.

Stay near popular Holliston attractions

Pinecrest Golf Club

6.0/10 (1 review)
This scenic par-66 course features tree-lined fairways and strategic challenges across 5,003 yards of rolling terrain. Practice at the 300-yard driving range before enjoying post-round dining at Anthony's on the Green.
See properties

Frequently asked questions

How much does a Holliston holiday package cost?
You can pick up a holiday package to this destination from €765 on Expedia. But how much your holiday to Holliston costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Holliston?
January, February and November are great times to search for cheap Holliston holiday packages. Choosing to travel in quieter periods means you can typically find better prices on flights and hotels.
How many days is enough for Holliston?
The ideal duration for your Holliston holiday depends on what you'd like to see. Typically, a handful of days to a week will give you time to go to all the main sights and explore some hidden gems along the way.
Is it worth booking a holiday package to Holliston?
Boasting a host of highlights starting with its amazing history, Holliston is a good holiday destination. Whether you want to visit sights like Pinecrest Golf Club and Pleasure Point or venture off the beaten track, you'll have plenty to see and do on your Holliston holiday.
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 holiday package as soon as possible.
Is it cheaper to book a Holliston holiday as a package?
You can enjoy significant savings on your Holliston break by booking a personalised holiday 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 holiday 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.
How to plan a trip to Holliston?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Holliston.
  2. Budget wisely: On top of the price of your accommodation, you'll need to consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Holliston.
  3. Decide how long to go for: Now that you're up to speed on Holliston, you can work out the ideal length of your holiday. Put together a draft plan and give yourself enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Holliston holiday package that brings all your bookings together.

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.