Wellesley Holidays from £679

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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.

Top Wellesley Flight + Hotel 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
per person
8 Nov - 11 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
29 Sept - 2 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The Boston Harbor Hotel continues to be my absolute favorite place to stay in Boston, and my recent visit reminded me exactly why. From the moment I walked through the doors, I was greeted by the same welcoming and professional staff that makes this property truly special. The team went above and beyond by upgrading me to a suite, which was an unexpected and much-appreciated gesture that really enhanced my stay. The suite itself was beautifully appointed and comfortable, providing the perfect retreat after busy days exploring the city. What really sets this hotel apart is its unbeatable location. You simply cannot find a better spot in Boston - it's perfectly positioned for both business and leisure activities, with easy access to everything the city has to offer while maintaining that sense of waterfront tranquility. Every stay here has been delightful, and the consistency in service quality is remarkable. The Boston Harbor Hotel has earned my loyalty through their attention to detail and genuine hospitality. I'm already looking forward to my next visit!

Reviewed on 11 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
29 Sept - 2 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on 11 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
29 Sept - 2 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Excellent hotel. Lovely accommodations, super helpful staff and great neighbourhood with lots of attractions and great restaurants near by.

Reviewed on 15 Aug 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
8/10 Very Good! (571 reviews)
I had the best sleep! This property was quiet, elegant, and perfectly met my needs. I was in for business and often hotels are so loud and crowded. This property was so quiet and I could not hear any street noise. When you travel, sleep can be hard to find. This was truly and oasis. Everything was clean and there were lots of amenities. Very close to the subway, food, and shopping. Will recommend.

Reviewed on 14 Aug 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

Top hotels in Wellesley

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 £205 per night from 24 Aug to 25 Aug
£205
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,824 reviews)
"The pool was great."

Reviewed on 15 Aug 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £168 per night from 1 Sept to 2 Sept
£168
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (3,199 reviews)
"The wicked small room is definitely small"

Reviewed on 14 Aug 2025

Hilton Boston Park Plaza
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 £162 per night from 24 Aug to 25 Aug
£162
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (1,612 reviews)
"Amazing"

Reviewed on 13 Aug 2025

citizenM Boston Back Bay
See all 3,532 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

Popular places to visit

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

What to do in Wellesley

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£59
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£52
per adult
86% 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

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.

* 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.