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Holidays to Wellesley

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Wellesley choose Expedia! Find everything you need to organise your trip to Wellesley in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top Hotel Deals

Spacious Private Entrance Master Bedroom/Bath
Spacious Private Entrance Master Bedroom/Bath
67 Donizetti St, Wellesley, MA

Situated in Wellesley, this apartment building is 1.5 mi (2.4 km) from Wellesley College and 2 mi (3.2 km) from Babson College. Cochituate State Park and Natick ...…

4.7/5Exceptional! (11 reviews)
perfect quarantine for me

"I wanted to quarantine after traveling home until I got a second negative PCR test enough days after my travel. This space has a separate entrance that keeps the owners safe and separate. The space is clean and pleasant with a very comfortable bed with very soft nice bed linens."…"

Reviewed on 20 Nov 2020

Spacious Private Entrance Master Bedroom/Bath
Gorgeous super clean newly renovated modern colonial
Gorgeous super clean newly renovated modern colonial
28 Hillside Rd, Wellesley, MA

Situated in Wellesley, this holiday home is 2.4 mi (3.8 km) from Babson College and within 6 miles (10 km) of Wellesley College and Brandeis University. Boston ...…

Gorgeous super clean newly renovated modern colonial
Wellesley Bed and Breakfast
Wellesley Bed and Breakfast
2.5 out of 5
28 Eaton Court, Wellesley, MA

Situated in Wellesley, this bed & breakfast is 1.3 mi (2.2 km) from Babson College and 2.5 mi (3.9 km) from Wellesley College. Boston College and Dana-Farber ...…

3.8/5Good! (24 reviews)
Great place to Watch the Marathon

"It was the perfect place to watch the Boston Marathon. We had to walk only a block to the race course. Elite runners come by around 10:30am. Catch all your running friends at the half way point, near mile 14.8 from the start. Walk across the street to the Wellesley Hills train station and catch the ..."…"

Reviewed on 17 Apr 2019

Wellesley Bed and Breakfast
See all 1937 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.

Top things to do in Wellesley

Image for Go Boston All-Inclusive: 45+ Attractions & Tours on 1 Pass

Go Boston All-Inclusive: 45+ Attractions & Tours on 1 Pass

£48
Per adult
76% of travellers recommend
Go Boston All-Inclusive: 45+ Attractions & Tours on 1 Pass
Image for New England Aquarium Admission

New England Aquarium Admission

£23
Per adult
84% of travellers recommend
New England Aquarium Admission
Image for Boston History & Highlights Small Group Tour

Boston History & Highlights Small Group Tour

£34
Per adult
90% of travellers recommend
Boston History & Highlights Small Group Tour
See all activities in Wellesley

Plan your Wellesley holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Wellesley. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation* , because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page. 
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Wellesley holiday package?
If your holiday plans in Wellesley have changed, it’s good to know that it’s possible to cancel your booking. If you booked less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your hotel, airline or car rental company may impose a fee. To learn more, check our Customer Service Portal.
When is the best time of year to visit Wellesley?
There’s a real advantage to taking your Wellesley holiday in . Typically, you can get the best deals around this time. , on the other hand, is the priciest time to visit. If you like the buzz of peak season, visit Wellesley in . The calmer months of will help you skip the crowds.
How far in advance should I book my Wellesley holiday?
It can be hard to know when is the ideal time to book your holiday to Wellesley. But generally the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels nearly 12 months prior to departure. If you’re thinking of a last-minute getaway, no need to worry! There are incredible bargains announced on Expedia all the time.
What should I know before booking a Wellesley travel package?
Whether it’s relaxation or adventure you’re craving, a Wellesley holiday package lets you organise your escape your way. Plus, you’ll score great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you’ll save!
Does Expedia offer Book Now, Pay Later Wellesley holiday packages?
Your bank balance shouldn’t stop you from getting the best out of your trip, so Expedia has devised a plan to help. Thanks to our partnership with online lender Affirm, it’s easier than ever to book an unforgettable getaway that won’t drain your wallet. Simply Book Now, Pay Later and take the hassle out of planning for your journey.