Sherborn Vacations from $822

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

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,314, price is now $822 per person
$822
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 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 $7,425, price is now $4,460 per person
$4,460
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

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,957, price is now $1,229 per person
$1,229
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again

Reviewed on May 25, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,741, price is now $1,767 per person
$1,767
per person
Aug 19 - Aug 24
found 2 days ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (685 reviews)
The staff went above and beyond... So helpful and courteous! Our room was spacious and immaculate, and the indoor pool and hot tub was an added bonus! Nice small bar attached to the lobby with a little restaurant for breakfast and lunch... we'll be back for sure!

Reviewed on Jun 1, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $2,065, price is now $1,349 per person
$1,349
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Staff was very nice and helpful.

Reviewed on May 28, 2026

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Discover the most popular places to visit in Sherborn

Fenway Park

Fenway Park

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

Fenway Park
Harvard University

Harvard University

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

Harvard University
Gillette Stadium

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

What to do in Sherborn

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Sherborn

Sherborn Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$258 nightly
The price is $301 total per night from Jun 7 to Jun 8
$301 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (4,677 reviews)
"Very disappointed in the aesthetics of the room in the artist tower. It felt awful waking up in the morning and looking at a concrete ceiling that looked unfinished. And also the corner pillars that were concrete and unfinished.There was no luggage rack to put your suitcase on and no closets. It ..."

Reviewed on Jun 1, 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $167 total per night from Jun 7 to Jun 8
$167 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (2,639 reviews)
"A unique hotel that we enjoyed. Very clean."

Reviewed on May 31, 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$288 nightly
The price is $334 total per night from Jun 28 to Jun 29
$334 total
Jun 28 - Jun 29
Total with taxes and fees
9.6/10 Exceptional! (4,402 reviews)
"This property is perfect! My only complaint is that when I booked it stated that we would have free breakfast and upon arrival they stated that we did not have breakfast included in our stay. Pretty disappointed but it did not take away from the beauty and cleanliness at this hotel"

Reviewed on Jun 1, 2026

Seaport Hotel Boston
See all 3,651 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 $822 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.

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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.