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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,994, price is now CA $1,758 per person
CA $1,758
per person
Jun 22 - Jun 27
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $3,492, price is now CA $2,087 per person
CA $2,087
per person
Jun 22 - Jun 27
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Staff was great room was cute!

Reviewed on Apr 10, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $5,722, price is now CA $3,647 per person
CA $3,647
per person
Jun 22 - Jun 27
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (248 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was CA $2,933, price is now CA $1,916 per person
CA $1,916
per person
Jun 22 - Jun 27
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9/10 Wonderful! (3,000 reviews)
Great location and clean!

Reviewed on Apr 11, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $2,668, price is now CA $1,758 per person
CA $1,758
per person
Jun 22 - Jun 27
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
10/10 Exceptional! (18 reviews)
We absolutely loved our stay at this new hotel. My family and I kept saying what a really nice hotel and the staff was great as well. The food at Ama (we ate breakfast) was delicious. The property is beautiful. Can’t wait to stay again.

Reviewed on Apr 5, 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
Worcester Central Business District

Worcester Central Business District

3 out of top 10 points of interest in this area
4.5/5(3 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

Embassy Suites by Hilton Boston Marlborough

Embassy Suites by Hilton Boston Marlborough

3.5 out of 5
123 Boston Post Rd W Marlborough MA
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Apr 23 to Apr 24
CA $210
CA $235 total
Apr 23 - Apr 24
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
My only negative for this property is that the room I was in had very thin walls and I could hear the neighboring room very well. Besides that it was excellent.

Reviewed on Apr 10, 2026

Embassy Suites by Hilton Boston Marlborough
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Apr 20 to Apr 21
CA $142
CA $159 total
Apr 20 - Apr 21
includes taxes & fees
9.2/10 Wonderful! (1,475 reviews)
Beautiful building, nice staff and clean comfortable room.

Reviewed on Apr 10, 2026

Wellsworth Hotel
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 $180 per night from May 6 to May 7
CA $180
CA $202 total
May 6 - May 7
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Staff were wonderful. Room was nice and quiet! We had a wonderful time.

Reviewed on Apr 8, 2026

DoubleTree by Hilton Hotel Boston - Westborough
See all 362 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 $1,758, 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

Old Mill Boathouse rowing sailing paddling center city of port moody Esplanade Ave Rocky Point Park Recreational Pier A rowing lesson on the water Teenagers are engaged in sports club 09.2022 Canada

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

DCU Center

4/5(3 reviews)

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

DCU Center

Things to do

1-Hour Axe Throwing in Worcester

1-Hour Axe Throwing in Worcester

CA $38
per adult
90% 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.