Southborough Vacations from $325

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Your Southborough Vacation

When an adventure in the city is calling your name, answer it with a Southborough vacation package. With all your travel arrangements taken care of before you leave, all you have to do here is concentrate on having fun. If your trip to Southborough includes some sightseeing, hit up renowned attractions like Westborough Country Club, Lake Chauncy Public Beach and Sudbury Reservoir. No matter your travel plans or budget, putting together the ultimate tailored Southborough vacation is a breeze with Expedia.

The Latest Southborough vacation packages

Price found within the past 48 hours. Click for updated prices.
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

2 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $485, price is now $325 per person
$325
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.4/10 Very Good! (268 reviews)
The kitchen isn't fully equipped for cooking. I found some culinary utensils incl. a pan and a pot. But there wasn't any stove to cook. The shops nearby are great incl. Trader Joe's and Maruichi.

Reviewed on Nov 4, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $1,189, price is now $667 per person
$667
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (460 reviews)
The entire experience at The Iris hotel was excellent form the Valet parking, the room, the bar & the restaurant. I would stay there anytime I'm in Brookline

Reviewed on Nov 22, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,224, price is now $736 per person
$736
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Clean room, staff is nice and helpful

Reviewed on Nov 29, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $971, price is now $644 per person
$644
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Our one night stay was really nice overall. Check in was at 3pm. We had show reservations that evening and they couldn’t get us into a room until 4:30 because they said many guests have perks from Amex w late check outs. We were super rushed because we were leaving for a show at 5:30 and while they said they would comp the lunch we ate while waiting for the room, we were still made to be late and still had to ask them to remove it from the bill at check out. All that aside it was lovely.

Reviewed on Dec 1, 2025

Lakeside Inn

Lakeside Inn

2 out of 5
Price was $553, price is now $377 per person
$377
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
7.6/10 Good! (2,303 reviews)
Great stay! Thank you! Loved the apples at check in!

Reviewed on Dec 1, 2025

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Southborough Hotel Deals

Red Roof Inn Boston - Southborough/ Worcester

Red Roof Inn Boston - Southborough/ Worcester

2 out of 5
367 Turnpike Rd Southborough MA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Dec 8 to Dec 9
$94 total
Dec 8 - Dec 9
Total with taxes and fees
7/10 Good! (1,001 reviews)
No car for me but did look like there was plenty of parking for people.

Reviewed on Oct 31, 2025

Red Roof Inn Boston - Southborough/ Worcester
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

2.5 out of 5
135 2nd Ave Waltham MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $96 total per night from Dec 21 to Dec 22
$96 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (1,548 reviews)
This was the 4th time I’ve stayed here since 2023 and each time has been great , no issues , staff is friendly , property is always clean and quiet and breakfast is perfect

Reviewed on Nov 25, 2025

Hampton Inn & Suites Boston/Waltham
Bedford Plaza Hotel - Boston

Bedford Plaza Hotel - Boston

3 out of 5
340 Great Road Bedford MA
Fully refundable
$55 nightly
The price is $62 total per night from Dec 3 to Dec 4
$62 total
Dec 3 - Dec 4
Total with taxes and fees
7/10 Good! (649 reviews)
Old place but seems like they're renovating

Reviewed on Nov 24, 2025

Bedford Plaza Hotel - Boston
See all 919 properties in Southborough
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 Southborough Vacation Packages

Southborough Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
9,700
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 Southborough vacation package cost?
You can snap up a vacation package to this popular destination from $325 on Expedia. But how much your vacation to Southborough costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Southborough?
If you're hoping to snag a cheap Southborough vacation package, consider traveling in February, March and December. You'll generally find better rates on flights and accommodations during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Southborough?
With a well-organized itinerary, you can easily tick off the top Southborough attractions in a handful of days. But if you want to venture off the beaten track or go on day trips, consider booking your Southborough vacation for longer.
How to find the best Southborough package deals?
Use Expedia's handy filters to help you find some unbeatable Southborough package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Southborough package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Southborough vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and stays separately. Better still, you can tailor your Southborough escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Southborough?
Secure amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Southborough adventure.
Does Expedia offer Book Now, Pay Later Southborough vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Southborough trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.