Wellesley Packages (Flight + Hotel)
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Top Wellesley Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
West End
฿33,869
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
Detroit (DTT) to Boston (BOS)
8.8/10 Excellent! (1,588 reviews)
Second time staying here and it didn’t disappoint. Was super clean, beds were very comfortable and there’s a garage to park in right next to the hotel. Bathrobes/slippers and the mini fridge are such a perk staying in this hotel too! We stayed here for a concert at TD Garden and the location couldn’t be better! We had a super nice gentleman check us in at the front desk, he was speedy, personable and helpful (he was from Madrid) they are lucky to have him! We visit Boston often and this is now one of our favorite places to stay!
Reviewed on 7 Sept 2026
The Wylie Inn and Conference Center at Endicott College
฿35,013
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
Detroit (DTT) to Boston (BOS)
9.2/10 Wonderful! (1,203 reviews)
While the rooms look recently redecorated and modern, the public spaces look very dated and basic. The linens (sheets, towels, etc.) are basic motel level. The pillows were downright awful. There was also significant road noise and sounds of planes overhead so I needed the white noise app to drown it out.
It was also disappointing to see that they still use tiny disposable toiletries (environmental nightmare but also not a good guest experience to try to eke out enough product for 2 people’s showers).
On the whole, it’s fine if you don’t have another option, but expect a more basic experience than you might expect from the photos.
Reviewed on 6 Sept 2026
Stay near popular Wellesley attractions
Wellesley College
7.0/10 (76 reviews)
Wellesley College enchants visitors with its 500-acre landscape featuring Lake Waban and notable architecture. Explore the Davis Museum's art collection or stroll through the beautiful Botanic Gardens.
Massachusetts Horticultural Society's Gardens at Elm Bank
Explore thirteen distinct gardens at this 36-acre horticultural haven, from the historic Italianate Garden to the Trial Garden. Stroll through vibrant seasonal blooms and find inspiration in landscape designs.
Keohane Sports Center
The Keohane Sports Centre serves as Wellesley College's athletic hub for 13 varsity teams. Visitors can enjoy state-of-the-art fitness equipment, indoor track, and Olympic-sized pool when guest access is available.
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
Eight well-maintained hard courts await tennis enthusiasts at this local Wellesley facility. Reserve through PlayLocal if you're a resident or enjoy evening play with a seasonal night tag.
What to do in Wellesley
Boston Old Town Trolley Hop-on Hop-Off City Tour
฿1,612
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
฿1,515
per adult
80% of travellers recommend
Frequently asked questions
How much does a Wellesley holiday package cost?
You can snap up a holiday package to this top destination from ฿31,352 on Expedia. But how much your holiday to Wellesley costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Wellesley?
The off-season is the best time to head to Wellesley if you're trying to save. Another tip for getting cheap Wellesley holiday packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Wellesley?
Usually, a handful of days is enough to explore the main attractions during your Wellesley holiday. However, if you prefer to have some time to relax or take day tours, consider extending your itinerary.
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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Wellesley holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking accommodation 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 holiday 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.
How to plan a trip to Wellesley?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Wellesley.
- Budget wisely: On top of the cost of your hotel, you should consider other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected costs that may crop up during your trip to Wellesley.
- Work out your trip length: Consider how much time you want to spend exploring Wellesley. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Bundle your airfare and accommodation: After you've nailed down your dates and duration, book the right Wellesley holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
