Wellesley Vacations from $627

Book a Hotel + Flight or Car together to unlock savings

  • 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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $886, price is now $627 per person
$627
per person
Mar 31 - Apr 4
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
I didn’t like that I was surprised with “hospitality fee” for almost $70 upon arrival. Had I known that I would’ve stayed somewhere else. That’s why I paid in advance on Expedia.

Reviewed on Jan 23, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,341, price is now $884 per person
$884
per person
Apr 5 - Apr 10
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
The staff was fantastic!

Reviewed on Jan 24, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $2,458, price is now $1,672 per person
$1,672
per person
Apr 16 - Apr 22
found 2 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,206, price is now $825 per person
$825
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
beautiful, clean rooms, well appointed

Reviewed on Jan 23, 2026

Don't see what you're looking for?
See all available trips from Columbus to Wellesley
View all trips

Discover the most popular places to visit in Wellesley

Nighttime baseball game at Fenway Park showcasing a vibrant atmosphere in Boston, Massachusetts

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
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

4.5/5(388 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
Boston Common showcases lush greenery and city skyline under a clear blue sky during a sunny day

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
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

$54
per adult
98% of travellers recommend
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions
Boston Celtics Basketball Game at TD Garden

Boston Celtics Basketball Game at TD Garden

$92
per adult
Boston Celtics Basketball Game at TD Garden
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
$158 nightly
The price is $184 total per night from Feb 1 to Feb 2
$184 total
Feb 1 - Feb 2
Total with taxes and fees
9.6/10 Exceptional! (3,935 reviews)
Room was spotless. Staff was accommodating and friendly. Only complaint is towels were too rough and stiff. Need a little bit softener. Otherwise, happy with my stay and will book there again in the future.

Reviewed on Jan 22, 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $153 total per night from Feb 8 to Feb 9
$153 total
Feb 8 - Feb 9
Total with taxes and fees
8.2/10 Very Good! (3,122 reviews)
The room was clean, nice, and the lobby was decorated super pretty for Christmas. We just hoped for streaming on the TV in the room

Reviewed on Jan 26, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$119 nightly
The price is $139 total per night from Jan 29 to Jan 30
$139 total
Jan 29 - Jan 30
Total with taxes and fees
9.2/10 Wonderful! (6,191 reviews)
Everything was great

Reviewed on Jan 26, 2026

Harborside Inn Of Boston
See all 3,963 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Wellesley vacation package cost?
You can snap up a vacation package to this top destination from $627 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.