Westborough Vacations from $500

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Your Westborough Vacation

The adventure-filled city of Westborough is calling. Discover its highlights and hidden gems with a Westborough vacation package that's customized to you. Westborough Country Club and Lake Chauncy Public Beach are a couple of the top attractions to visit during a trip to Westborough. Expedia can help you escape the everyday. Tailor your vacation to Westborough to suit your style of travel, whatever that may look like.

The Latest Westborough vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
Save 100% on your flight
Price was $757, price is now $500 per person
$500
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
8.8/10 Excellent! (1,007 reviews)
good place, location, room was nicely decorated; good bar and lobby

Reviewed on May 25, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,875, price is now $1,111 per person
$1,111
per person
Aug 8 - Aug 11
found 9 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again

Reviewed on May 25, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $7,421, price is now $4,739 per person
$4,739
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $2,055, price is now $1,368 per person
$1,368
per person
Jul 29 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Fantastic Hotel. Loved the location, room was clean, staff was helpful, and loved the amenities.

Reviewed on May 25, 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was $1,026, price is now $726 per person
$726
per person
Aug 8 - Aug 11
found 9 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
8.4/10 Very Good! (1,451 reviews)
We had a nice stay in terms of it being a convenient clean place to lay our heads. However the room was quite small and the price was high for it being just a place to sleep. They also offered no amenities at the time specifically not being able to provide water was annoying. The staff however was very polite and apologetic as the hotel was going through some changes. Parking was close by and cheaper than other hotels which was another reason we ended up here so at least that delivered. Overall it was an okay stay at a dated hotel. Bring your own water!😅

Reviewed on May 26, 2026

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Discover the most popular places to visit in Westborough

Westborough Country Club

4.5/5(5 reviews)

Enjoy a round of golf in Westborough at Westborough Country Club. Experience the great live music or attend a sporting event in this family-friendly area.

Westborough Country Club

What to do in Westborough

Niagara Fall

Niagara Falls(US) 2-Day Tour from Boston

$375
per adult
Niagara Falls(US) 2-Day Tour from Boston
Boston: Niagara Falls Night Tour with Fireworks

Boston to Niagara Falls One Way Intercity Transfer with Optional Upgrade

$99
per adult
Boston to Niagara Falls One Way Intercity Transfer with Optional Upgrade
See all activities in Westborough

Westborough Hotel Deals

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
$127 nightly
The price is $141 total per night from Jun 11 to Jun 12
$141 total
Jun 11 - Jun 12
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"Breakfast was very good but too expensive. Continental breakfast should be complimentary."

Reviewed on May 27, 2026

DoubleTree by Hilton Hotel Boston - Westborough
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
$104 nightly
The price is $116 total per night from May 28 to May 29
$116 total
May 28 - May 29
Total with taxes and fees
6.6/10 (999 reviews)
"The room smelled like athlete foot no matter how much air freshener I sprayed. The toilet seat has stained. The floor was dirty."

Reviewed on May 25, 2026

Extended Stay America Suites Boston Westborough Computer Dr
Extended Stay America Suites Boston Westborough Connector Rd

Extended Stay America Suites Boston Westborough Connector Rd

2.5 out of 5
19 Connector Rd Westborough MA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $122 total per night from May 28 to May 29
$122 total
May 28 - May 29
Total with taxes and fees
6/10 (807 reviews)
"I LOVE IT SO MUCH!"

Reviewed on May 25, 2026

Extended Stay America Suites Boston Westborough Connector Rd
See all 589 properties in Westborough
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.

Find the Best Westborough Vacation Packages

Westborough Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
4,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Lake Chauncy Public Beach, Sudbury Reservoir and The Silver Buffalo Gallery

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Frequently asked questions

How much does a Westborough vacation package cost?
Offering great value package deals from $500 on Expedia, you'll be pleasantly surprised at how much a vacation to Westborough costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Westborough?
February, November and December are the best times to look for cheap Westborough vacation packages. Choosing to travel in less busy months means you can generally find lower prices on flights and accommodations.
How many days is enough for Westborough?
The ideal length for your Westborough vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to visit all the leading sights and explore some hidden treasures along the way.
How to find the best Westborough package deals?
Begin your search for a Westborough package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Westborough package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Westborough escape off to a flying start.
Is it cheaper to book a Westborough vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Westborough vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Westborough?
If you're planning a spur-of-the-moment Westborough getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Westborough?

  1. Choose your travel dates: What you plan to do in Westborough and your preferred season will help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your hotel will likely be the biggest expense during your trip to Westborough.
  3. Use Expedia's trip planning tool to explore Westborough: Research every aspect of your trip to Westborough with this comprehensive planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide your trip length: Think about how long you want to spend discovering Westborough. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  5. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, book the right Westborough vacation package for you.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Explore some of the top things to do in Westborough in Westborough and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Westborough vacation packages?
Your Westborough break is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.