Wellesley Holidays from £933

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Your Wellesley Holiday

Reserve a Wellesley holiday package and prepare to experience everything this city has to offer. Consider staying in the neighbourhood 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 organising your ideal holiday to Wellesley now.

The Latest Wellesley Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
8 Sept - 14 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
7/10 Good! (145 reviews)
Amazing location right by the water, quiet building and clean. But the furniture is really uncomfortable, particularly the couch which is the only seating, it’s a pull out bed so the entire sofa sinks in low. The bed isn’t solid and easily slides off the frame just by sitting on it. We also had a delivery order stolen from the front desk area.

Reviewed on 25 Jun 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
6 Aug - 11 Aug
found 22 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Quiet hotel with superior service and great amenities near to all of the sites in Boston.

Reviewed on 23 Jun 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.4/10 Exceptional! (347 reviews)
The staff were very helpful. The hotel is exceptionally clean and well appointed.

Reviewed on 6 Jun 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Always a classic; service levels are as expected (quite good but this isn't a 5-star hotel and isn't priced as one). Cori isn't the world's most enthusiastic lab but she's still great; my daughter looked forward to meeting her going in and out of the hotel, which is exactly why I chose it. Will be back!

Reviewed on 27 Jun 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
19 Aug - 26 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (3,026 reviews)
Room was very spacious and clean. Extra toiletries was a big help!

Reviewed on 29 Jun 2025

The Verb Hotel

The Verb Hotel

3.5 out of 5
Fenway–Kenmore
Save 100% on your flight
per person
11 Sept - 18 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,733 reviews)
Super convenient for Fenway and the green line. Will stay again!

Reviewed on 28 Jun 2025

Wellesley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
28,000
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Boston Museum of Fine Arts, Museum of Science and Isabella Stewart Gardner Museum

Our pick of the best Wellesley Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Stay at this 4-star spa hotel in Boston. Enjoy free Wi-Fi, a full-service spa and 4 restaurants. Our guests praise the breakfast and the pool in their reviews. ...
9/10 Wonderful! (3,621 reviews)
"Great vibe! Good people very helpful"

Reviewed on 29 Jun 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Stay at this 4-star hotel in Boston. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Popular attractions Fenway Park and Copley Square ...
9.2/10 Wonderful! (1,316 reviews)
"Friendly and helpful staffs, excellent team!"

Reviewed on 27 Jun 2025

citizenM Boston Back Bay
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Stay at this 4-star eco-certified hotel in Boston. Enjoy free Wi-Fi, 2 restaurants and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (2,976 reviews)
"Staff and service was top notch!"

Reviewed on 27 Jun 2025

Seaport Hotel Boston
See all 3,498 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Wellesley holiday with Expedia?
With great-value flights, car hire and accommodation options all in one place, Expedia makes arranging your Wellesley holiday a cinch. Moreover, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Select from fabulous stays, add flights and/or a hire car (and maybe even some fun activities!) and get unbeatable prices. Had a change of plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, check out our Customer Service Portal link.
When is the best time of year to holiday in Wellesley?
If you love the excitement that comes with peak season, visit Wellesley in June, July and August. If you're looking for a calmer vibe, November, December and January will suit you better. Arrange your getaway to Wellesley according to what kind of holiday you're looking for. January is the coolest month, when daytime temperatures average -2ºC. In July, the warmest period, you can expect averages of 23ºC during the day.
What are the top hotels for my holiday in Wellesley?
If you're planning to stay in the Wellesley Hills neighbourhood, Wellesley Bed and Breakfast and US Open HSE are terrific options. Babson Park is another well-known Wellesley area. We recommend Lovely Studio Walk to Wellesley and Babson College or Spacious Private Entrance Master Bedroom/Bath if you choose this part of town.
How do I get a cheap holiday to Wellesley?
Lock in flights that suit your schedule, add a hotel to your booking and watch the savings grow with a Wellesley holiday. It's that easy! From hotels and flights to hire cars and tours, Expedia is your gateway to cheap travel. And with over 400 partner airlines and 321,000 properties worldwide to choose from, you won't be short of choice. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Wellesley holiday?
There are so many things to keep you busy while enjoying a holiday in Wellesley. Boston College, Bentley College, Wellesley College and Brandeis University are just a few of this city's top attractions.
What is the best area to stay in when on holiday in Wellesley?
Wellesley has lots of wonderful places to explore, such as Wellesley College. Stay somewhere close by and make sightseeing hassle-free.
Do I need a visa for my Wellesley holiday?
Look up the most up-to-date information on official government websites. Your nationality and whether you're visiting for business, study or leisure will determine if you'll require a visa for Wellesley. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Submit your application well in advance to allow sufficient processing time. Some visas can take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Wellesley holiday?
Do some research into the types of things people in Wellesley wear, and maybe even look up style blogs for some fashion inspiration. Try to create a versatile wardrobe with pieces that suit your destination and showcase your unique style. Check the weather forecast so you can pack accordingly. The warmest month in Wellesley is July, with average daytime temperatures of 23ºC. If you're holidaying in the coolest month of January, the mercury averages -2ºC during the day.
What does an Expedia Wellesley holiday include?
With Expedia, you can select a combination of flights, car hires and hotels to create your ideal Wellesley travel package. Once you've made your booking, simply add on the fun things like sightseeing tours and activities. Don't forget --- the more you bundle, the more cash you'll save! Private holiday homes and apartments are a couple of popular property types in Wellesley. No matter your holiday style or size of your group, you can rely on Expedia for the flexibility to personalise your dream escape.
Does Expedia offer Book Now, Pay Later Wellesley holidays?
Expedia has teamed up with online lender Klarna to make booking your next getaway easier on your wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that works with your budget. Consider these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's easy instalment plans. If paying in multiple transactions works for you, choose this option at checkout.
  • No-deposit holidays: When you come across an unbeatable deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.

Can I choose my airline with a Wellesley Expedia holiday?
The choice is all yours! Expedia has access to more than 400 partner airlines all over the world, so you can tailor your Wellesley escape according to your style and budget.

Discover the most popular places to visit in Wellesley

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

Fenway Park

4.5/5(61 reviews)

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

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 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 a skyscraper, landscape views and a park

Boston Common

4.5/5(204 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

Unmissable things to do in Wellesley

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£58
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£40
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

£25
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Wellesley

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.