Wellesley Holidays

Photo by Lisa Frackiewicz

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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 S$327 per night from 24 Aug to 25 Aug
S$327
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,799 reviews)
"The best in the seaport!"

Reviewed on 9 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 S$293 per night from 1 Sept to 2 Sept
S$293
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (3,198 reviews)
"Very convenient. Very efficient."

Reviewed on 10 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 S$290 per night from 17 Aug to 18 Aug
S$290
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (1,589 reviews)
"A really great hotel in a wonderful location. With super-comfy beds, lovely linen and all mod cons, the room is small but perfectly formed. I was surprised that despite the busy road outside, it really is quiet and tranquil inside. Everything works, too - seems like an obvious point but not always ..."

Reviewed on 10 Aug, 2025

citizenM Boston Back Bay
See all 3,518 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.

Popular places to visit

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

Fenway Park

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

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
New England Aquarium

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

What to do in Wellesley

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$101
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

S$90
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

S$44
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Wellesley

Frequently asked questions

How much does a Wellesley holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday to Wellesley costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Wellesley?
The off-season is the best time to head to Wellesley if you're trying to save. Another tip for getting cheap Wellesley holiday packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Wellesley?
Usually, a handful of days is enough to explore the main attractions during your Wellesley holiday. However, if you prefer to have some time to relax or take day tours, consider extending your itinerary.
How to find the best Wellesley package deals?
Bagging a cheap Wellesley package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Wellesley package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Wellesley holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking accommodation and flights separately. Better still, you can tailor your Wellesley escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Wellesley?
If you're planning an impromptu Wellesley getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Wellesley?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Wellesley.
  2. Budget wisely: On top of the cost of your hotel, you should consider other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected costs that may crop up during your trip to Wellesley.
  3. Work out your trip length: Consider how much time you want to spend exploring Wellesley. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, book the right Wellesley holiday package for you.

* 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.