Wellesley Holidays

Photo by Lisa Frackiewicz

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Top Flight + Hotel Deals in Wellesley

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was €1,311, price is now €1,034 per person
€1,034
per person
28 Oct - 31 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (3,154 reviews)
It is an extraordinary place. Walked in stressed, walked out soooo relaxed! The hotel is exquisite, the staff is so friendly, happy, and go beyond anything I have ever encountered. The service was better than when I stay at a Four Seasons hotel, which is excellent! I RECOMMEND THIS RESORT TO EVERYONE! You MUST stay once in your life!!!

Reviewed on 20 Aug 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was €1,524, price is now €1,153 per person
€1,153
per person
28 Oct - 31 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,055 reviews)
This property was very nice with a great location lots of cool amenities. The front desk staff was amazing and answered every question we had. Overall, it was a very good stay and we would stay here again.

Reviewed on 20 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was €1,873, price is now €1,425 per person
€1,425
per person
28 Oct - 31 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
The beds are the main thing that keep me coming black, so comfortable, especially after a long day of walking around Boston. I will say we were disappointed that the inside of our coffee machine was very dirty.. something i think shouldn't be missed when cleaning since we love a good morning coffee in the room , but had to settle for going to a coffee shop. We tried ordering room service , but after waiting over 1hr we ended up calling to cancel it. For the amount of money we paid , i think they could step their game up when it comes to service and details.

Reviewed on 16 Aug 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was €1,670, price is now €1,284 per person
€1,284
per person
28 Oct - 31 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,010 reviews)
Great boutique hotel! Excellent staff and locations.

Reviewed on 20 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was €1,599, price is now €1,233 per person
€1,233
per person
28 Oct - 31 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on 16 Aug 2025

Top hotels in Wellesley

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €174 per night from 24 Aug to 25 Aug
€174
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,689 reviews)
Hands down AMAZING
"Our stay was amazing from start to finish! The check in staff was super helpful. Our room was ready earlier than expected which was great after travel. The hotel was close to everything, great food, great shopping and of course right beside TD Garden. The best part was the view from our room. Get ..."

Reviewed on 20 Aug 2025

citizenM Boston North Station
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 €166 per night from 1 Sept to 2 Sept
€166
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,260 reviews)
"Wonderful area!"

Reviewed on 20 Aug 2025

Seaport Hotel Boston
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 €259 per night from 24 Aug to 25 Aug
€259
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,850 reviews)
It’s okay
"It was cool but the elevator button didn’t work for my floor. There is also a lot of ghetto people enjoying being hood rich for a weekend, be aware."

Reviewed on 18 Aug 2025

Omni Boston Hotel at the Seaport
See all 3,537 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 night scenes and a sporting event 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 which includes heritage architecture and a city

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

€68
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

€61
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

€29
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 from €1,034 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.