Wellesley Vacations from $306

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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 Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $478, price is now $306 per person
$306
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,156 reviews)
Absolutely loved it all- hip new vibe. Easy going staff at the ready. Gorgeous rooms and the ‘down the hall bathroom’ was across from room and all amenities perfect. Private bathroom suites. Parking right around the corner. Such a good 24 hours in Boston!

Reviewed on Sep 13, 2025

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $647, price is now $389 per person
$389
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,240 reviews)
What a great place with friendly staff!

Reviewed on Sep 14, 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $580, price is now $368 per person
$368
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,742 reviews)
Great morning coffee! And water readily available!

Reviewed on Sep 15, 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Save 100% on your flight
Price was $1,885, price is now $1,218 per person
$1,218
per person
Oct 22 - Oct 29
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,105 reviews)
Great property for travelers looking for proximity to Harvard (walking) and Fenway (short Uber). It had a fun, funky vibe and the rooms were clean and comfortable. An adjoining room option was available which made travel with my group even better. The games and access to restaurant were a plus. I wish the restaurant opened earlier but that is not up to the Allston. There is a McDonald’s nearby which was a nice option in the morning as the breakfast protein was hard boiled eggs every day. I would stay again for sure!

Reviewed on Sep 14, 2025

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $553, price is now $358 per person
$358
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,906 reviews)
Comfortable, well maintained hotel with friendly staff.

Reviewed on Sep 9, 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
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 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 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 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
$267 nightly
The price is $310 total per night from Sep 21 to Sep 22
$310 total
Sep 21 - Sep 22
Total with taxes and fees
9.6/10 Exceptional! (3,381 reviews)
"Quiet location. Close to public transportation to get all around Boston! Free bikes to explore."

Reviewed on Sep 10, 2025

Seaport Hotel Boston
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
$271 nightly
The price is $316 total per night from Sep 22 to Sep 23
$316 total
Sep 22 - Sep 23
Total with taxes and fees
9/10 Wonderful! (3,950 reviews)
"It was a nice hotel and great shower pressure"

Reviewed on Sep 9, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $226 total per night from Sep 21 to Sep 22
$226 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (3,755 reviews)
"The property itself was quite good. Standouts were the lobby area and the view from the room. Not-so-nice were the cubicle bathrooms that had minimal privacy and the extra soft beds (personal preference though I understand). Overall I would recommend but be aware the beds are very soft, the bathrooms ..."

Reviewed on Sep 11, 2025

citizenM Boston North Station
See all 3,523 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.

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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 $306 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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