Wellesley Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.
Fairmont Copley Plaza, Boston
The Inn at Hastings Park, Relais & Chateaux - Boston
Boston Harbor Hotel
Raffles Boston
Encore Boston Harbor

Ready to book your vacation to Wellesley?

 

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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
The price is CA $289 per night from Aug 10 to Aug 11
CA $289
CA $393 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,666 reviews)
"The hotel was clean and staff was friendly."

Reviewed on Jul. 12, 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
The price is CA $252 per night from Jul 13 to Jul 14
CA $252
CA $293 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,408 reviews)
"Always a great stay"

Reviewed on Jul. 11, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is CA $282 per night from Jul 13 to Jul 14
CA $282
CA $329 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (5,302 reviews)
"this property was perfect for our stay in Bostain. First of all the room was large, clean and very comfortable. The front desk staff was very pleasant. The best part about this hotel is the location. You are on the waterfront and within walking distance of everything you need including many tours. ..."

Reviewed on Jul. 10, 2025

Harborside Inn Of Boston
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.

Discover the most popular places to visit in Wellesley

What to do in Wellesley

Frequently asked questions

How much does a Wellesley vacation package cost?
You can pick up a vacation package to this top destination from CA $891 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.