Wellesley Holidays from £793

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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.
Lakeside Inn

Lakeside Inn

2 out of 5
Price was £1,044, price is now £793 per person
£793
per person
21 Sept - 27 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
7.6/10 Good! (2,371 reviews)
large room overlooking the lake was nice. Breakfast was decent. Situated within easy driving distance to Boston. With no housekeeping (which i am ok with) there should have been more trashcans around. i would stay there again defitely.

Reviewed on 7 Jul 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,049, price is now £1,383 per person
£1,383
per person
30 Aug - 3 Sept
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
A beautiful Hotel w an excellent staff that provides superior service and helps to make our stay memorable. We will be back again.

Reviewed on 6 Jul 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was £1,678, price is now £1,134 per person
£1,134
per person
26 Sept - 1 Oct
found 17 hours ago
Return direct flight included
London (LHR) to Boston (BOS)
9.4/10 Exceptional! (158 reviews)
Lovely hotel!

Reviewed on 6 Jul 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was £1,486, price is now £1,061 per person
£1,061
per person
13 Aug - 18 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on 23 May 2026

Blue Iris

Blue Iris

2.5 out of 5
Nantucket Town
Price was £1,717, price is now £1,336 per person
£1,336
per person
14 Sept - 18 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9/10 Wonderful! (91 reviews)
Great

Reviewed on 30 Jun 2026

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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is £167 per night from 26 Jul to 27 Jul
£167
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (2,419 reviews)
"The staff at the Hyatt in Cambridge was outstanding! Everyone was friendly, cheerful, and efficient, and they truly went above and beyond to make our stay special. They were happy to accommodate additional requests for our room and provided excellent recommendations for local entertainment and travel. ..."

Reviewed on 7 Jul 2026

Hyatt Regency Boston/Cambridge
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is £190 per night from 26 Jul to 27 Jul
£190
26 Jul - 27 Jul
includes taxes & fees
9.6/10 Exceptional! (4,530 reviews)
"Was very near to harbour and other amenities . The room was very clean and had everything you could require for a good stay . Ate here on one evening and the food was good and a 15 dollar discount per person, made it even better value . Was not the best location for public transport as seemed to ..."

Reviewed on 6 Jul 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is £138 per night from 2 Aug to 3 Aug
£138
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (2,718 reviews)
"We had another wonderful stay at The Revolution Hotel. Its a lovely hotel, very clean and beautiful! In a perfect area that is centrally located. The shared bathrooms are NOT shared bathrooms. “Shared” sounds very intimidating, but they are actually individual bathroom suites. So you walk into the ..."

Reviewed on 6 Jul 2026

The Revolution Hotel
See all 3,916 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.
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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.
See properties

What to do in Wellesley

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

£39
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

£60
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

£36
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
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.

Explore a world of travel with Expedia

* 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.