Wellesley Vacations from $411

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Your Wellesley Vacation

Reserve a Wellesley vacation package and prepare to experience everything this city has to offer. Consider staying in the neighborhood of East Cambridge, which is good for shopping, markets and bars and pubs. If your trip to Wellesley includes a little sightseeing, take in renowned attractions like Wellesley College, Brandeis University and Babson College. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Wellesley now.

The Latest Wellesley vacation packages

Price found within the past 48 hours. Click for updated prices.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was $572, price is now $411 per person
$411
per person
Feb 12 - Feb 17
found 8 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
7.4/10 Good! (802 reviews)
The staff are easy to work with.

Reviewed on Dec 2, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,173, price is now $1,155 per person
$1,155
per person
Feb 9 - Feb 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Excellent hotel in all aspects. Comfortable and spacious rooms and attentive staff. Only exception is $70 valet parking which is way over priced (even for Boston) especially on a weekend evening.

Reviewed on Dec 7, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,592, price is now $952 per person
$952
per person
Feb 9 - Feb 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $1,203, price is now $877 per person
$877
per person
Feb 12 - Feb 17
found 8 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (460 reviews)
Clean room, nice staff, good location, would definitely recommend staying here.

Reviewed on Dec 7, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $933, price is now $683 per person
$683
per person
Feb 9 - Feb 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,196 reviews)
Good, clean, I am satisfied

Reviewed on Dec 3, 2025

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Discover the most popular places to visit in Wellesley

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
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
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

What to do in Wellesley

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 Bruins Ice Hockey Game at TD Garden

Boston Bruins Ice Hockey Game at TD Garden

$155
per adult
Boston Bruins Ice Hockey Game at TD Garden
Odyssey Boston Premier Elegant Dinner Cruise

City Cruises Boston: Premier Elegant Dinner Cruise

$241
per adult
City Cruises Boston: Premier Elegant Dinner Cruise
See all activities in Wellesley

Wellesley Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $219 total per night from Dec 18 to Dec 19
$219 total
Dec 18 - Dec 19
Total with taxes and fees
9.6/10 Exceptional! (3,774 reviews)
Great stay! Staff was on point!

Reviewed on Dec 7, 2025

Seaport Hotel Boston
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
$199 nightly
The price is $232 total per night from Dec 14 to Dec 15
$232 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (4,257 reviews)
Room was clean and modern. The coffee shop in the lobby was pretty good. Walking distance to snow port. Did not like all the surprise charges for various taxes that totaled another $150.

Reviewed on Dec 3, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street Boston MA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Dec 14 to Dec 15
$125 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (4,139 reviews)
No faceclothes. Bathroom wasn't very "private." Excellent window shade function.

Reviewed on Dec 1, 2025

citizenM Boston North Station
See all 3,728 properties in Wellesley
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 Wellesley Vacation Packages

Wellesley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
28,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Boston Museum of Fine Arts, Museum of Science and Isabella Stewart Gardner Museum

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Frequently asked questions

How much does a Wellesley vacation package cost?
You can snap up a vacation package to this top destination from $411 on Expedia. But how much your vacation to Wellesley costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Wellesley?
You can usually find reduced prices and better availability in November, December and January. Take a look at our cheap Wellesley vacation packages and you could score some great off-season discounts.
How many days is enough for Wellesley?
The ideal length of your Wellesley vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to hit all the major sights and explore some hidden spots along the way.
How to find the best Wellesley package deals?
Bagging a cheap Wellesley package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Wellesley package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Wellesley vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights separately. Better still, you can tailor your Wellesley escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Wellesley?
If you're planning an impromptu Wellesley getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Wellesley vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Wellesley vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great 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.