Wellesley Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Wellesley

Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$258 per night from 21 Dec to 22 Dec
S$258
includes taxes & fees
21 Dec - 22 Dec
9.6/10 Exceptional! (2,589 reviews)
"Amazing"

Reviewed on 20 Nov,2024

Seaport Hotel Boston
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 S$253 per night from 8 Dec to 9 Dec
S$253
includes taxes & fees
8 Dec - 9 Dec
8.2/10 Very Good! (3,285 reviews)
"I’ll start with the bad- laying in bed getting ready for bed and a mouse goes running across the floor. I notified front desk and was moved to another room. The good- the staff was friendly, the breakfast buffet was well stocked, and is centrally located to a lot of amenities."

Reviewed on 21 Nov,2024

Hilton Boston Park Plaza
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$291 per night from 30 Nov to 1 Dec
S$291
includes taxes & fees
30 Nov - 1 Dec
8.6/10 Excellent! (2,860 reviews)
"I couldn’t be more impressed with the level of service. From the moment I arrived the front desk staff went above and beyond to make me feel welcome. Check-in was smooth and efficient. Throughout my stay, the entire staff always responded and assisted promptly and kindly."

Reviewed on 20 Nov,2024

Omni Parker House
See all 3,038 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.

Frequently asked questions

How much does a Wellesley holiday package cost?
Maybe less than you might think — from only , in fact! By combining flights, hotels and car rentals into your own tailor-made travel package, your getaway to Wellesley is just clicks away.
How do I get a cheap travel package to Wellesley?
Combine your hotel and flight bookings, toss in extras such as activities or a rental car, and save with a Wellesley holiday package. You won’t just score superb discounts on your trip — you’ll have lots of choice at your fingertips too. When you book with Expedia, you’ll have your pick of over 550 airlines and 1,000,000 hotels around the globe. Your dream holiday starts right here, right now!
Where should I stay in Wellesley?
A holiday in Wellesley isn’t complete without visiting Wellesley College, Babson College and Belkin Family Lookout Farm. Spend your evenings near these tourist attractions and make sightseeing simple.
What are the top hotels in Wellesley?
Travellers going to Wellesley often make a reservation at Spacious Private Entrance Master Bedroom or Wellesley Bed And Breakfast. These options are in Wellesley Hills. Another great neighbourhood is Babson Park. Us Open Hse and Lovely Studio Walk To Wellesley And Babson College are recommended options in this area.
How far in advance should I book my Wellesley holiday?
It can be hard to know exactly when is the perfect time to book your Wellesley holiday. But generally the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels nearly 12 months before departure. If you’re considering a last-minute getaway, no need to worry! There are great deals posted on Expedia every single day.
What does an Expedia Wellesley travel package include?
Flights, rental cars and hotels — we have them covered. With Expedia, you can shape your Wellesley package however you want. All you have to do is figure out what you need. Once you’ve made your booking, you can add on fun things like activities and experiences. The more you bundle, the bigger your savings!
What should I know before booking a Wellesley travel package?
Locking in all the parts of your escape together is an excellent way to save. Combine your car rentals, airfares and hotels into a convenient little package. But it’s not just hotels. Expedia has all sorts of properties, including holiday rentals such as beachside villas and spacious residences. The list goes on!
Can I choose my airline with a Wellesley Expedia holiday package?
Expedia has access to more than 550 airline partners globally, so you sure can! Simply select your preferred carrier and put together your ideal Wellesley trip.
If I'm not able to travel, can I cancel my Wellesley holiday package?
Certainly, and we’ll help you every step of the way. You may be able to amend or cancel your Wellesley holiday package for free within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your holiday, visit our Customer Service Portal for more information.

Popular places to visit

Fenway Park showing 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 featuring 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

What to do in Wellesley

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$97
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Admission Tickets

View Boston Observation Deck Admission Tickets

S$33
Per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
Whale-Watching Cruise in Stellwagen Bank Marine Sanctuary

Boston Harbor New England Aquarium Whale-Watching Cruise

S$105
Per adult
86% of travellers recommend
Boston Harbor New England Aquarium Whale-Watching Cruise
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.