Wellesley Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Lisa Frackiewicz

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Wellesley Vacation Packages

Wellesley 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
The price is ₩249,626 per night from Sep 1 to Sep 2
₩249,626
₩347,085 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,851 reviews)
"Amazing girls wkd. Pool was so nice to have and room and beds comfy and clean!"

Reviewed on Aug 24, 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
The price is ₩268,415 per night from Sep 1 to Sep 2
₩268,415
₩312,579 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,682 reviews)
"Great location, the staff were very friendly."

Reviewed on Aug 22, 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ₩207,537 per night from Sep 1 to Sep 2
₩207,537
₩248,593 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,273 reviews)
"Our second stay at the Seaport Hotel and everything was amazing. We will continue to use this hotel for all of our Boston visits."

Reviewed on Aug 24, 2025

Seaport Hotel Boston
See all 3,538 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.

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
New England Aquarium featuring marine life

New England Aquarium

4.5/5(1,678 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Frequently asked questions

How much does a Wellesley vacation package cost?
You can snap up a vacation package to this top destination 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?
The off-season is the best time to head to Wellesley if you're trying to save. Another tip for getting cheap Wellesley vacation packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Wellesley?
Usually, a handful of days is enough to explore the main attractions during your Wellesley vacation. However, if you prefer to have some time to relax or take day tours, consider extending your itinerary.
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.
How to plan a trip to Wellesley?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Wellesley.
  2. Budget wisely: On top of the cost of your hotel, you should consider other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected costs that may crop up during your trip to Wellesley.
  3. Work out your trip length: Consider how much time you want to spend exploring Wellesley. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the right Wellesley vacation package for you.

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