Holliston Vacations from $697

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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.

The Latest Holliston vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Save 100% on your flight
Price was $1,117, price is now $697 per person
$697
per person
Jun 6 - Jun 12
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (261 reviews)
It’s a comfortable and friendly place.

Reviewed on May 1, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was $4,464, price is now $2,739 per person
$2,739
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $1,639, price is now $1,018 per person
$1,018
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (66 reviews)
It's a relatively nea property, so very clean. Rooms are good. Location is amazing as it overlooks the HBS campus. The staff can do better by providing ready solutions to their customers when required and coordinate better with each other. Thos can enhance the experience for sure!

Reviewed on May 6, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $3,477, price is now $2,166 per person
$2,166
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had

Reviewed on May 2, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,911, price is now $1,198 per person
$1,198
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
8.8/10 Excellent! (1,451 reviews)
First time in Boston and it was perfect. Would book again.

Reviewed on May 2, 2026

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Discover the most popular places to visit in Holliston

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

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
$177 nightly
The price is $198 total per night from May 24 to May 25
$198 total
May 24 - May 25
Total with taxes and fees
8.4/10 Very Good! (2,889 reviews)
Upon arrival the people at the front desk were extremely pleasant and helpful. Our room was clean and fresh. We ate at the Social and the staff were extremely friendly and efficient. Food was delicious, superbly prepared and very fresh ingredients. The shower was great, plenty of hot water and pressure, ...

Reviewed on May 7, 2026

Four Points by Sheraton Boston Newton
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

2 out of 5
220 Huntington Avenue Boston MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $220 total per night from May 25 to May 26
$220 total
May 25 - May 26
Total with taxes and fees
8.2/10 Very Good! (303 reviews)
One complaint..the room was too cold for the timevof year. You couldn't turn the heat..apparently, Boston had an unexpected heatwave in April so the hotel turned thr a/c on ahead of schedule and can't turn the heat back on until the fall! NOT GOOD! The place was very convenient and the staff was ...

Reviewed on May 6, 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
$188 nightly
The price is $219 total per night from May 25 to May 26
$219 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (2,643 reviews)
Hands down my favorite hotel chain. Only disappointment was that the website implies that the kitchen is available 24/7, but it actually meant that snacks were available 24/7. Otherwise, my stay was great! Staff is friendly & helpful, the location is ideal, & the views are beautiful.

Reviewed on May 7, 2026

citizenM Boston Back Bay
See all 2,244 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.

Find the Best Holliston Vacation Packages

Holliston Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
14,000
Top Sights
Hopkinton State Park, Fun and Games Family Entertainment Center and Ashland State Park

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Frequently asked questions

How much does a Holliston vacation package cost?
You can pick up a vacation package to this destination from $697 on Expedia. But how much your vacation to Holliston costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Holliston?
If you're hoping to snag a cheap Holliston vacation package, consider planning a trip in December, January and February. You'll typically find better prices on flights and accommodations during these months — ideal for budget-conscious travelers.
How many days is enough for Holliston?
The ideal length of your Holliston vacation depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to visit all the leading attractions and discover some hidden gems along the way.
Is it worth booking a vacation package to Holliston?
Boasting a host of highlights starting with its top-notch history, Holliston is a good vacation destination. Whether you'd like to explore sights such as Pinecrest Golf Club and Pleasure Point or venture off the beaten track, you'll find loads to see and do on your Holliston vacation.
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 vacation package as soon as possible.
Is it cheaper to book a Holliston vacation as a package?
You can enjoy significant savings on your Holliston break by booking a personalized vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Holliston vacation packages?
Your Holliston break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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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.