Webster Square Vacations from ￥251,196

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The Latest Webster Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul 17, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Great small boutique hotel. European feel and service. Lovely small garden in back. Good food.

Reviewed on Aug 11, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (3,154 reviews)
It was such a good stay, we had a beautiful view and i wish we stayed longer.

Reviewed on Aug 14, 2025

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,623 reviews)
I wasn't thrilled. I'm not going to be dishonest I paid a lot I told them it was my boyfriend's 50th here they told me they would give us a tough choice surprise in the room but not a charcuterie and all we got were some Ritz crackers and a couple strawberries and some cheddar. But also they would not Park our truck. There was no warning about trucks not being welcome at ballet. I didn't really have any kind of upgrade overview I paid $700 for two nights the restaurants are never open and I paid $6 for coffee in the morning

Reviewed on Aug 13, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,021 reviews)
We have always loved staying at the Copley. It’s beautiful with old Boston charm. The history of the hotel is fascinating. The staff goes above and beyond to make your stay memorable!

Reviewed on Aug 14, 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
Worcester Central Business District showing heritage architecture and a city

Worcester Central Business District

3 out of top 10 points of interest in this area
4/5(116 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 ￥13,120 per night from Aug 17 to Aug 18
￥13,120
￥14,655 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,457 reviews)
"It’s such a unique property and hard to “rate”. The room was extremely dated, but spacious and comfortable for the most part. The property is sprawling and locating our building took a while. There was a wedding there the night we stayed and it really took over…everything. Made for a later and noisier ..."

Reviewed on Aug 12, 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 ￥13,118 per night from Aug 17 to Aug 18
￥13,118
￥14,653 total
Aug 17 - Aug 18
includes taxes & fees
6.4/10 (914 reviews)
"Excellent staff"

Reviewed on Aug 5, 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 ￥17,552 per night from Aug 21 to Aug 22
￥17,552
￥19,605 total
Aug 21 - Aug 22
includes taxes & fees
8.6/10 Excellent! (1,001 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.

Frequently asked questions

How much does a Webster Square vacation package cost?
From as low as ￥251,196, 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

Worcester Art Museum which includes heritage architecture and signage

Worcester Art Museum

4.5/5(29 reviews)

You can spend an afternoon studying the exhibits at Worcester Art Museum in Worcester. You can attend a sporting event while in the area.

Worcester Art Museum

Worcester Polytechnic Institute

4.5/5(78 reviews)

Explore the campus of Worcester Polytechnic Institute, during your trip to Worcester. Attend a sporting event in this family-friendly area.

Worcester Polytechnic Institute

Things to do

1-Hour Axe Throwing in Worcester

1-Hour Axe Throwing in Worcester

￥4,135
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.