Wellesley Vacations from $402

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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.
John Carver Inn & Spa

John Carver Inn & Spa

3 out of 5
Plymouth Cultural District
Save 100% on your flight
per person
Oct 4 - Oct 8
found 21 hours ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
8/10 Very Good! (1,006 reviews)
Room was average. Kind of disappointed that the restaurant and bar were closed. Didn’t really offer a lot of information about the area. The building was having maintenance while , outside painting.

Reviewed on Jul 12, 2025

Josiah Keith House

Josiah Keith House

2 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 30
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (21 reviews)
The inn keeper was available at all times and very attentive to our stay. The history of the home given by the inn keeper was interesting and informative. Highly recommend.

Reviewed on Jun 24, 2025

Ocean Air Suites

Ocean Air Suites

2.5 out of 5
Hampton Beach
Save 100% on your flight
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
9.4/10 Exceptional! (34 reviews)
location was awesome. able to see fireworks right from deck in the back. It’s definitely family friendly would definitely be coming back again next year :)

Reviewed on Sep 3, 2024

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
per person
Sep 23 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
The Beverly

The Beverly

3 out of 5
Save 100% on your flight
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.4/10 Very Good! (313 reviews)
Large room but bathroom was small. We didn’t get maid service the day before we left and because we were in the basement our towel didn’t dry so our last shower was drying with a damp towel. The bottom landing was scary because you couldn’t see that it had a step down. They need to color it so you can see it.

Reviewed on Jul 14, 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

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

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

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

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
$246 nightly
The price is $287 total per night from Aug 10 to Aug 11
$287 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (3,674 reviews)
Great for short city breaks, not a relaxing pool
"Overall I enjoyed my stay at the Omni Boston Hotel at the Seaport. The staff were incredibly helpful and the room was lovely and clean. The hotel's ideal for a City break, and would stay again, though not for a relaxing pool stay. The pool area, whilst overlooking the main road, is lovely. My experience ..."

Reviewed on Jul 13, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Jul 20 to Jul 21
$214 total
Jul 20 - Jul 21
Total includes taxes and fees
9.2/10 Wonderful! (1,424 reviews)
"Loved this hotel. Friendly staff"

Reviewed on Jul 13, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
$229 nightly
The price is $267 total per night from Jul 20 to Jul 21
$267 total
Jul 20 - Jul 21
Total includes taxes and fees
9/10 Wonderful! (5,326 reviews)
"Comfortable enough rooms. TV could have been larger Excellent location. MTA to aprt. steps from hotel. Would definitely consider staying again. 4.3/5"

Reviewed on Jul 14, 2025

Harborside Inn Of Boston
See all 3,509 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

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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 $402 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.