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

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,062, price is now CA $590 per person
CA $590
per person
Nov 1 - Nov 3
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,563, price is now CA $1,038 per person
CA $1,038
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
Phil’s property is immaculate and the rooms are very clean and will all required amenities. Phil’s hospitality is also top notch and it will be my place to stay in my future cape cod visits!!

Reviewed on Aug. 20, 2025

Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $994, price is now CA $679 per person
CA $679
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (18 reviews)
We’d love to come back here.

Reviewed on Aug. 22, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was CA $1,051, price is now CA $725 per person
CA $725
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
Great stay at an amazing locations. No issues we had a blast. They were so welcoming and inviting and the room was clean and comfortable.

Reviewed on Aug. 23, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $1,545, price is now CA $1,078 per person
CA $1,078
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (585 reviews)
The location was great and we were able to get to all the sites easily. Also, liked having two beds and two bathrooms for the price. However, everything was very cheap in there. The sheets were nubbie because they were cheap and worn. The toliet paper was so awful we had to buy our own. The beds had little support. The place was clean though. So if you don't care much about the bed, sheets, and toliet paper it is a good pick. If you do maybe pick somewhere else.

Reviewed on Aug. 17, 2025

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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
The price is CA $249 per night from Sep 1 to Sep 2
CA $249
CA $347 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,840 reviews)
"Overall a great hotel. Well located, the seaport zone is really beautiful. Public transportation access"

Reviewed on Aug. 21, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Sep 1 to Sep 2
CA $268
CA $312 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,680 reviews)
"I missed the 11:30pm train but thankfully Citizens is right next door. I was able to book the room and check in within 10 minutes. I was so happy with my room, I had an amazing view. Nice clean shower and space for a single person or couple. Will always stay at Citizens when I go to Boston now!"

Reviewed on Aug. 21, 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 1 to Sep 2
CA $210
CA $252 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,259 reviews)
"We liked that the beds were comfortable and the AC was quiet. The food at the hotel was delicious. The pool was also very nice."

Reviewed on Aug. 22, 2025

Seaport Hotel Boston
See all 3,538 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Wellesley

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 reviews)

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 which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities 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 $590 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.