Wellesley Vacation Packages
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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.
Top Wellesley Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $665
per person
Sep 7 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Good Hotels Boston
South End
CA $1,494
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.
Reviewed on May 23, 2026
Ready to book your vacation to Wellesley?
Wellesley Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $265
CA $356 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (4,688 reviews)
"Room service would be useful and a better stocked convenience store within the hotel is needed."
Reviewed on Aug 6, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $234
CA $272 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (2,801 reviews)
"A great value! The shared bathroom thing is only a minor inconvenience. It's essentially a room that has 6-ish doors, each with their own toilet and shower, so it's very private. Be aware that they don't straighten your room everyday either. Overall, for what we spent, it was worth giving up these ..."
Reviewed on Aug 6, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $335
CA $447 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (4,861 reviews)
"The Omni was overall a fantastic hotel to stay in. The location was great. The staff was very approachable and friendly. There was always someone there to help. It was convenient to have restaurants on site as well as 24 hour room service. We stayed in an artist king studio. The room was clean and ..."
Reviewed on Aug 6, 2026
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.
Stay near popular Wellesley attractions
Wellesley College
7.0/10 (76 reviews)
Take a campus tour or just explore the area of Wellesley College, during your trip to Wellesley. Amble around this vibrant area's riverfront or attend a sporting event.
Massachusetts Horticultural Society's Gardens at Elm Bank
Enjoy an outing to Massachusetts Horticultural Society's Gardens at Elm Bank during your stay in Wellesley. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Keohane Sports Center
Catch an event at Keohane Sports Center during your trip to Wellesley. While you're in the area, wander around the gardens.
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
Catch an event at Hunnewell Tennis Center during your trip to Wellesley. While you're in the area, wander around the gardens.
What to do in Wellesley
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $48
per adult
86% of travellers recommend
Frequently asked questions
How much does a Wellesley vacation package cost?
You can pick up a vacation package to this top destination from CA $665 on Expedia. But how much your vacation to Wellesley costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Wellesley?
Plan your getaway for the off-season and you're likely to get cheap Wellesley vacation packages. Bear in mind that school vacation periods and local events and festivals can have an impact on prices, so do some research before you go.
How many days is enough for Wellesley?
Dedicate around 3 days for your Wellesley vacation if you're hoping to discover all that makes this destination unique. Wander around key neighbourhoods, including Auburndale and South Side. Then tick off major sights such as Cochituate State Park and Shoppers World. With a good itinerary, you can keep busy with room for some relaxation too. Want to travel beyond Wellesley? Consider fitting in a day trip or two.
How to find the best Wellesley package deals?
Start your search for a Wellesley package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Wellesley package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wellesley adventure off to a flying start.
Is it cheaper to book a Wellesley vacation as a package?
You can enjoy significant savings on your next Wellesley retreat by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Wellesley?
If you're planning a spontaneous Wellesley adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Wellesley?
- Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to vacation in Wellesley.
- Set your budget: Consider expenses like flights, food and transportation when calculating how much to set aside for your trip to Wellesley. Then, select a property that fits your budget, whether that's an affordable option or a high-end retreat.
- Decide your trip length: Consider how long you'd like to spend exploring Wellesley. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Wellesley vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
