Wellesley Vacations from $725
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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.
Four Seasons Hotel Boston
Bay Village
$1,232
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
Stay near popular Wellesley attractions
Wellesley College
7.0/10 (76 reviews)
Wellesley College enchants visitors with its 500-acre landscape featuring Lake Waban and notable architecture. Explore the Davis Museum's art collection or stroll through the beautiful Botanic Gardens.
Massachusetts Horticultural Society's Gardens at Elm Bank
Explore thirteen distinct gardens at this 36-acre horticultural haven, from the historic Italianate Garden to the Trial Garden. Stroll through vibrant seasonal blooms and find inspiration in landscape designs.
Wellesley College Botanic Gardens
Explore the great outdoors at Wellesley College Botanic Gardens, a lovely green space in Wellesley. While you're in the area, wander around the gardens.
Hunnewell Tennis Center
Eight well-maintained hard courts await tennis enthusiasts at this local Wellesley facility. Reserve through PlayLocal if you're a resident or enjoy evening play with a seasonal night tag.
Keohane Sports Center
The Keohane Sports Center serves as Wellesley College's athletic hub for 13 varsity teams. Visitors can enjoy state-of-the-art fitness equipment, indoor track, and Olympic-sized pool when guest access is available.
What to do in Wellesley
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
$46
per adult
80% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
$37
per adult
92% of travellers recommend
Wellesley Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$298 nightly
$347 total
Nov 11 - Nov 12
Total with taxes and fees
9.2/10 Wonderful! (4,903 reviews)
"Omni was a great place to stay, within walking distance from both the Silver Line from the airport and to the Black Falcon cruise port. Every staff member was wonderful, helpful and generous. The place is huge, and gorgeous. On our return after our cruise, they let us pay a small fee to hold our ..."
Reviewed on Oct 14, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$129 nightly
$150 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (2,977 reviews)
"Enjoy hotel - nice location - a vibe - mostly shared bathroom down the hall but individual shower rooms and not that bad to deal with"
Reviewed on Oct 14, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
$254 total
Oct 30 - Oct 31
Total with taxes and fees
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 $725 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.
