Holliston Vacations from $266

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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.
All Seasons Inn & Suites

All Seasons Inn & Suites

2.5 out of 5
Save 100% on your flight
Price was $372, price is now $266 per person
$266
per person
Apr 29 - May 3
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Providence (PVD)
6.6/10 (716 reviews)
We stay at All Seasons often. It’s clean and inexpensive compared to what’s around that area.

Reviewed on Nov 9, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,296, price is now $842 per person
$842
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $669, price is now $441 per person
$441
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,891 reviews)
The people there were absolutely wonderful. We’ll stay there again next time in Boston! Great location near the theater District. Easy parking attached to the hotel.

Reviewed on Feb 1, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $672, price is now $447 per person
$447
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Thank you for the cool corner suite on the 9th floor! We stayed over after attending a Bruins game. Short stay but nice place. Good location for our adventures. We’ll stay again if when we are back in Boston! Ty

Reviewed on Jan 29, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,484, price is now $1,013 per person
$1,013
per person
Apr 3 - Apr 6
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 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

The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
61 Exeter Street Boston MA
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $215 total per night from Feb 15 to Feb 16
$215 total
Feb 15 - Feb 16
Total with taxes and fees
9.6/10 Exceptional! (1,360 reviews)
Room was great. Nice view and quiet as well. Food was excellent at their restaurants as was the bourbon! Staff were very helpful and quick to accommodate any request we had. Highly recommend this hotel as it is within walking distance of most attractions shops and restaurants and was clean and comfortable. ...

Reviewed on Feb 1, 2026

The Lenox Hotel Boston
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Feb 17 to Feb 18
$125 total
Feb 17 - Feb 18
Total with taxes and fees
9.2/10 Wonderful! (2,289 reviews)
Clean room. Great staff!

Reviewed on Feb 3, 2026

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
$79 nightly
The price is $92 total per night from Feb 8 to Feb 9
$92 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (3,933 reviews)
good

Reviewed on Feb 2, 2026

Copley Square Hotel, a FOUND Hotel
See all 2,223 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 $266 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.