Wellesley Vacations from $295

Book a Hotel + Flight or Car together to unlock savings

Photo by Lisa Frackiewicz
  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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 Wylie Inn and Conference Center at Endicott College
Boston Lodge and Suites
Iris Hotel Boston
Staypineapple, A Delightful Hotel, South End
The Merchant
Don't see what you're looking for?
See all available trips from Columbus to Wellesley
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Discover the most popular places to visit in Wellesley

What to do in Wellesley

Wellesley Hotel Deals

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street Boston MA
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $146 total per night from Dec 13 to Dec 14
$146 total
Dec 13 - Dec 14
Total with taxes and fees
9.2/10 Wonderful! (4,107 reviews)
Rooms were clean, staff was friendly

Reviewed on Nov 25, 2025

citizenM Boston North Station
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
$174 nightly
The price is $203 total per night from Dec 18 to Dec 19
$203 total
Dec 18 - Dec 19
Total with taxes and fees
9/10 Wonderful! (4,246 reviews)
Room ready when we arrived at 8:30am Small but suffices Noise from outside is easily heard

Reviewed on Nov 25, 2025

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
$90 nightly
The price is $105 total per night from Dec 14 to Dec 15
$105 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (2,279 reviews)
The room a stay itself were wonderful. A 20 minute walk or quick train ride to any sight we wanted to see. Parking was limited to only the local garage, which had a discounted rate of $35/day through the hotel. Otherwise, the streets in the area were permit parking only.

Reviewed on Nov 24, 2025

The Revolution Hotel
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

More vacations you might like

Frequently asked questions

How much does a Wellesley vacation package cost?
You can snap up a vacation package to this top destination from $295 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

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