Webster Square Vacation Packages

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Top Holiday Package Deals in Webster Square

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The Boston Harbor Hotel continues to be my absolute favorite place to stay in Boston, and my recent visit reminded me exactly why. From the moment I walked through the doors, I was greeted by the same welcoming and professional staff that makes this property truly special. The team went above and beyond by upgrading me to a suite, which was an unexpected and much-appreciated gesture that really enhanced my stay. The suite itself was beautifully appointed and comfortable, providing the perfect retreat after busy days exploring the city. What really sets this hotel apart is its unbeatable location. You simply cannot find a better spot in Boston - it's perfectly positioned for both business and leisure activities, with easy access to everything the city has to offer while maintaining that sense of waterfront tranquility. Every stay here has been delightful, and the consistency in service quality is remarkable. The Boston Harbor Hotel has earned my loyalty through their attention to detail and genuine hospitality. I'm already looking forward to my next visit!

Reviewed on Aug. 11, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Oct 30 - Nov 2
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9.4/10 Exceptional! (360 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on Aug. 4, 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,326 reviews)
Great stay as always! Miss the room service coming on actual plates but other than that it was excellent!

Reviewed on Aug. 12, 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,055 reviews)
The property was close to our family’s apartment, and also close to restaurants and parks.

Reviewed on Aug. 17, 2025

Where to stay in Webster Square

Find the best Webster Square areas and neighborhoods for the activities you enjoy most. Learn more about Webster Square
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Worcester Central Business District

3 out of top 10 points of interest in this area
5/5(2 area reviews)

If you're spending some time in Worcester Central Business District, DCU Center and Mechanics Hall are top sights worth seeing.

Find hotels in Worcester Central Business District

Webster Square Hotel Deals

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Aug 18 to Aug 19
CA $123
CA $138 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,459 reviews)
"Stayed many times. Remember if you stay in the motor lodge, it is a MOTOR LODGE. It is clean, comfortable, and convenient. It is not a 5 star hotel. We love the place, the value for the dollar is great!"

Reviewed on Aug. 14, 2025

Publick House Historic Inn and Country Motor Lodge
Extended Stay America Suites Boston Westborough Computer Dr

Extended Stay America Suites Boston Westborough Computer Dr

2.5 out of 5
1800 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Aug 18 to Aug 19
CA $124
CA $139 total
Aug 18 - Aug 19
includes taxes & fees
6.4/10 (918 reviews)
"The information on the website that this hotel offers free breakfast is very misleading . They only serve coffee, and there is no sitting area, like most hotels have. I did choose this hotel because of free breakfast and I'm disappointed. Natalie at check in was very helpful ."

Reviewed on Aug. 15, 2025

Extended Stay America Suites Boston Westborough Computer Dr
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
5400 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Aug 24 to Aug 25
CA $165
CA $184 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"I liked that the property had a restaurant & a bar."

Reviewed on Aug. 12, 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 345 properties in Webster Square
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 Webster Square vacation package cost?
From as low as CA $760, you can build your own Webster Square package the way you want. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Webster Square?
Bundle your hotels and flights with Expedia to save big bucks on your next big adventure. With over 550 partner airlines and 1,000,000 properties around the globe, your Webster Square vacation package can be customized exactly to suit your travel style. With all that extra money, why not throw in one or two interesting activities and tours? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Webster Square is much closer than you thought!
Where should I stay in Webster Square?
With so much to explore in Webster Square, it makes sense to lock in a hotel near its attractions. DCU Center, College of the Holy Cross and Clark University are some good ones to add to your to-do list.
What are the top hotels in Webster Square?
When it comes to comfy places to stay in Webster Square, you can't go past Modern Lakeside Single Family Home. Look up its deals and score a bargain.
How far in advance should I book my Webster Square vacation?
You'll be rewarded with the biggest variety at the cheapest prices by booking your trip to Webster Square early. Airlines tend to release tickets around a year before departure, so secure your spot ASAP. That said, Expedia is committed to giving you the best deals around, so there's never a bad time to book your dream vacation!
What does an Expedia Webster Square travel package include?
Expedia has all you need to organize your Webster Square escape, but what goes into your package is your call. Choose from any combination of hotels, flights and rental cars. Looking for some activities or tours to fill in your time? Once you've made your booking, you can add them too. No matter your style or budget, there's a deal to meet your needs.
What should I know before booking a Webster Square travel package?
An Expedia travel package can be customized for your circumstances and is a fantastic way to make your money go further. How little or much you include is completely up to you. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with a Webster Square Expedia vacation package?
Most definitely. Expedia has access to more than 550 airlines around the world, so you can design your Webster Square escape according to your budget and needs.
If I'm not able to travel, can I cancel my Webster Square vacation package?
We get it — sometimes life doesn't go according to plan. If you've locked in a Webster Square vacation package and have to amend or cancel it, we can help. We suggest looking up our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in Webster Square

DCU Center

Catch an event at DCU Center during your trip to Worcester. Attend a sporting event in this family-friendly area.

DCU Center

Regatta Point Park

Explore the great outdoors at Regatta Point Park, a lovely green space in Worcester. Attend a sporting event in this family-friendly area.

Regatta Point Park

Things to do

1-Hour Axe Throwing in Worcester

1-Hour Axe Throwing in Worcester

CA $39
per adult
100% of travellers recommend
1-Hour Axe Throwing in Worcester
See all activities in Worcester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.