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.
Raffles Boston
Back Bay
CA $1,481
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (312 reviews)
The room is beautiful, minimalist, luxurious, and extremely comfortable. In my opinion, it’s perfect for a solo traveler or, especially, for a couple. Since the room is on the smaller side, I personally wouldn’t consider it ideal for families traveling with children.
For a romantic getaway, however, it was absolutely perfect. One of the highlights is having an incredible and highly sought-after restaurant right inside the building. The dining experience was exceptional — the food was impeccable, the atmosphere was beautiful, and it truly added another level to our stay. I highly recommend making the restaurant part of the experience.
To make our stay even more special, I hired a local company, Our Love Box (@ourlovebox on Instagram), to create a romantic surprise in the room. I ordered a gorgeous bouquet of 100 roses along with a full romantic room setup, and the result was absolutely stunning.
What impressed me even more was how seamless everything was. They handled the entire setup and came back the following day to remove all of the decorations. Once they were finished, you couldn’t even tell there had been a setup in the room — everything was left exactly as it was before.
Overall, the entire experience was incredible. Between the luxurious and comfortable room, the exceptional dining experience, and the romantic setup, it was truly memorable. I highly recommend this experience for couples celebrating an anniversary, birthday, proposal, or simply looking for a special
Reviewed on Sep 21, 2026
The Langham, Boston
Downtown Boston
CA $1,453
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,007 reviews)
Beautiful property, very plush bedding and well-appointed rooms. We enjoyed a wonderful night of sleep!
Reviewed on Sep 23, 2026
Ready to book your vacation to Wellesley?
Wellesley Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $398
CA $521 total
Oct 25 - Oct 26
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $361
CA $468 total
Oct 25 - Oct 26
includes taxes & fees
9.6/10 Exceptional! (5,023 reviews)
"Arrived for a concert at Leader Bank Pavillion. Location was PERFECT! Walking distance to almost everything in the seaport district including the concert venue. Only complaint was the couch in the room was a little stained, but overall wonderful stay."
Reviewed on Sep 24, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $330
CA $384 total
Oct 25 - Oct 26
includes taxes & fees
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.
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.
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.
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 $69
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $117
per adult
92% 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 $1,066 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.
