Webster Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Webster Square

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,536, price is now CA $991 per person
CA $991
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,564, price is now CA $1,227 per person
CA $1,227
per person
Dec 24 - Dec 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,406, price is now CA $1,579 per person
CA $1,579
per person
Jan 29 - Feb 1
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,643, price is now CA $1,156 per person
CA $1,156
per person
Dec 15 - Dec 18
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $3,106, price is now CA $2,195 per person
CA $2,195
per person
Dec 27 - Dec 31
found 3 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)
Overall Excellent! clean room, very nice staff

Reviewed on Nov 4, 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 $131 per night from Nov 8 to Nov 9
CA $131
CA $147 total
Nov 8 - Nov 9
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 $125 per night from Nov 8 to Nov 9
CA $125
CA $139 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (1,805 reviews)
"We love this hotel, for the beauty of its grounds, the cleanliness of its rooms,its pet friendliness and its dining room that serves New England classic dishes, even Indian pudding."

Reviewed on Nov 5, 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 $130 per night from Nov 8 to Nov 9
CA $130
CA $148 total
Nov 8 - Nov 9
includes taxes & fees
Motel 6 Framingham, MA - Boston West
See all 393 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 $991, 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.