Webster Square Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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
Price was CA $1,411, price is now CA $706 per person
CA $706
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,415, price is now CA $2,164 per person
CA $2,164
per person
Jan 12 - Jan 19
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,975, price is now CA $1,259 per person
CA $1,259
per person
Jan 12 - Jan 19
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)
Great service!

Reviewed on Nov 8, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,397, price is now CA $1,548 per person
CA $1,548
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,234, price is now CA $1,488 per person
CA $1,488
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it.

Reviewed on Nov 8, 2026

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
A historic building with a red brick facade and arched windows.

Worcester Central Business District

4 out of top 10 points of interest in this area

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

Sonesta Select Boston Milford

Sonesta Select Boston Milford

3 out of 5
10 Fortune Blvd Milford MA
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Nov 11 to Nov 12
CA $133
CA $148 total
Nov 11 - Nov 12
includes taxes & fees
Sonesta Select Boston Milford
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 $126 per night from Nov 9 to Nov 10
CA $126
CA $141 total
Nov 9 - Nov 10
includes taxes & fees
9.2/10 Wonderful! (1,809 reviews)
"Room was nice, very good for the price, clean, shower was a little outdated, the restaurant was amazing! Turkey dinner and Mac n cheese! Delicious very friendly staff! Will definitely be returning!"

Reviewed on Nov 7, 2026

Publick House Historic Inn and Country Motor Lodge
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd Framingham MA
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Nov 9 to Nov 10
CA $125
CA $142 total
Nov 9 - Nov 10
includes taxes & fees
Motel 6 Framingham, MA - Boston West
See all 394 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Webster Square vacation package cost?
From as low as CA $706, 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.

Stay near popular Webster Square attractions

John J. Binienda Memorial Beach

Why not spend a lazy afternoon at John J. Binienda Memorial Beach during your trip to Worcester?
See properties

Things to do

1-Hour Axe Throwing in Worcester

1-Hour Axe Throwing in Worcester

CA $40
per adult
94% 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.