Sherborn Vacations from $625

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Your Sherborn Vacation

When you organize a vacation package to Sherborn, you can relax and enjoy your break knowing your travel plans have been made in advance. Uncover the many gems of this vibrant city from your base in a neighborhood like Auburndale, which is good for golfing. You'll want to sightsee during your trip to Sherborn. Swing by famous attractions like Wellesley College, Framingham State University and Shoppers World. Check out Expedia's wide range of travel options and begin planning your perfect vacation to Sherborn today.

The Latest Sherborn vacation packages

Price found within the past 48 hours. Click for updated prices.
Josiah Keith House

Josiah Keith House

2 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (21 reviews)
The inn keeper was available at all times and very attentive to our stay. The history of the home given by the inn keeper was interesting and informative. Highly recommend.

Reviewed on Jun 24, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The staff is excellent, especially in the restaurants. The food was great and the bed was very comfortable. The AC in both rooms worked well and everything was clean.

Reviewed on Jul 14, 2025

The Windsor Inn

The Windsor Inn

2.5 out of 5
Central Square
Save 100% on your flight
per person
Aug 23 - Aug 30
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (5 reviews)
The property is like a home, in fact it is a home. The owner runs the hotel, he is a food lover himself and makes different dishes for his guests. Further lots of food options for self service at any time of the day are available. And most importantly, the price is relatively low for this area. And there is no compromise on quality at all.

Reviewed on Oct 3, 2022

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Awesome stay with everything you need

Reviewed on Jul 13, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Sep 28 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Location is perfect. A lots of places to see within walking distance and good restaurants nearby too. The service is great. Friendly and professional staff. The room is clear and spacious. The gym is very big with all the equipments and have personal training rooms too. We stayed 5 nights and were very lucky to get room on 16th floor with a balcony!

Reviewed on Jul 14, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Sherborn

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(1,966 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Sherborn

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$54
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

$30
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
See all activities in Sherborn

Sherborn Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
$246 nightly
The price is $287 total per night from Aug 10 to Aug 11
$287 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (3,674 reviews)
Great for short city breaks, not a relaxing pool
"Overall I enjoyed my stay at the Omni Boston Hotel at the Seaport. The staff were incredibly helpful and the room was lovely and clean. The hotel's ideal for a City break, and would stay again, though not for a relaxing pool stay. The pool area, whilst overlooking the main road, is lovely. My experience ..."

Reviewed on Jul 13, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
$184 nightly
The price is $214 total per night from Jul 20 to Jul 21
$214 total
Jul 20 - Jul 21
Total includes taxes and fees
9.2/10 Wonderful! (1,426 reviews)
"Epic"

Reviewed on Jul 14, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
$229 nightly
The price is $267 total per night from Jul 20 to Jul 21
$267 total
Jul 20 - Jul 21
Total includes taxes and fees
9/10 Wonderful! (5,332 reviews)
"Very nice staff; We wish that they have a coffe maker;since is a good hotel"

Reviewed on Jul 15, 2025

Harborside Inn Of Boston
See all 3,236 properties in Sherborn
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 Sherborn Vacation Packages

Sherborn Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
4,300
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Hopkinton State Park, Fun and Games Family Entertainment Center and Ashland State Park

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Frequently asked questions

How much does a Sherborn vacation package cost?
You can pick up a vacation package to this destination from $625 on Expedia. But how much your vacation to Sherborn costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Sherborn?
December, January and February are the best times to search for cheap Sherborn vacation packages. Traveling in quieter periods means you can generally find lower prices on accommodations and flights.
How many days is enough for Sherborn?
With a well-organized schedule, you can easily hit the top Sherborn sights in a handful of days. But if you'd like to discover hidden spots or take day trips, think about booking your Sherborn vacation for longer.
How to find the best Sherborn package deals?
Start your search for a Sherborn package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune 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 Sherborn package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sherborn escape underway.
Is it cheaper to book a Sherborn vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still get the flexibility to create a customized Sherborn vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Sherborn?
If you've got your Sherborn travel dates finalized, book early to score some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Sherborn vacation packages?
If you're anything like us, you love discovering new places but don't love the big 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 Sherborn trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.