Book Exclusive Wellesley Vacation Packages

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Wellesley flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,272, price is now CA $971 per person
CA $971
per person
Nov 24 - Nov 27
found 17 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was CA $2,836, price is now CA $1,714 per person
CA $1,714
per person
Nov 6 - Nov 9
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,666, price is now CA $1,645 per person
CA $1,645
per person
Dec 10 - Dec 14
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $3,201, price is now CA $2,034 per person
CA $2,034
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Harbor and Boston Common are located nearby.
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,533, price is now CA $1,891 per person
CA $1,891
per person
Nov 6 - Nov 9
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Top Wellesley hotels deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $327 per night
CA $327
CA $439 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions Boston Harbor and Boston Common are located nearby.
Pool
Hot tub
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $355 per night
CA $355
CA $461 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Boston Harbor and Boston Common are located nearby.
Pool
Pet-friendly
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
The price is CA $334 per night
CA $334
CA $389 total
Oct 29 - Oct 30
includes taxes & fees
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Pet-friendly
Free WiFi
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $301 per night
CA $301
CA $409 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this luxury hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Pet-friendly
Free WiFi
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
The price is CA $437 per night
CA $437
CA $558 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Boston Harbor and Boston Common are located nearby.
Pet-friendly
Free WiFi
Omni Parker House

Omni Parker House

4.5 out of 5
60 School St Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $516 per night
CA $516
CA $659 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
Pet-friendly
Free WiFi
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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.

Stay near popular Wellesley attractions

Wellesley College

7.0/10 (76 reviews)
Take a campus tour or just explore the area of Wellesley College, during your trip to Wellesley. Amble around this vibrant area's riverfront or attend a sporting event.
See properties

Wellesley Vacations

Experiencing the true essence of Wellesley starts with knowing the basic details. Ready to find out just where this unique destination is and what you can do there?

This town is located 3 miles (5 kilometers) northwest of Needham. It's also 4 miles (6 kilometers) east of Natick.

Traveling is all about meeting people, so why not make pals with some of the 28,000 locals who reside in this part of Massachusetts?

Places to visit in Wellesley

Whether you like to think of yourself as a scholarly type or you just want to find out a little more about the region's long history of academics, Wellesley College is sure to enlighten and educate. Want some more ideas? Over the years, countless great thinkers and trailblazers have studied within the classrooms of Brandeis University. Learn about its rich history and accomplishments, and wander the campus during a tour. But there's more. If you and your travel pals are looking for somewhere to regroup, Shoppers World is a good option. Chat over a coffee and peruse the stores for that perfect keepsake.

Where do you fly into for Wellesley?

Get ready for some unforgettable new experiences! The center of Wellesley is approximately 14 miles (23 kilometers) west of Logan International Airport (BOS).

Frequently asked questions

How much are vacation packages to Wellesley?
Your vacation fantasies can become a reality in Wellesley from as little as CA $971. Packages include flights and hotels, so organizing everything should be a piece of cake. The only thing you'll need to worry about is having a good time.
How long should my Wellesley vacation be?
Generally, 2 nights is what most tourists book for their Wellesley vacation. That's a good starting point, but there's loads more to uncover if you allow yourself a little more time.
Where can I get the best vacation package deals for Wellesley?
Travelocity will be able to help you get a terrific Wellesley package deal. With 400 air carriers and 1,000,000 properties worldwide, you're sure to be able to craft the perfect itinerary.
Why should I book my Wellesley vacation package with Travelocity?
We offer round-the-clock support, top-notch service and a Price Match Guarantee. Life's a great big journey — and we have enticing destinations for you to journey to all across the globe. Travel with us and make your hip pocket happy.
Can I save on my Wellesley car rental if I combine it with my hotel or flight?
You sure can — bundle your flight, car and hotel into a Wellesley vacation package and you can save a tidy sum. With so much to discover in Wellesley, having your own wheels will come in handy. Once you're in the driver's seat, turn up the tunes and head toward Plymouth Rock, a must-see attraction roughly 64 kilometers from Wellesley.
Which airport is best for Wellesley?
Logan Intl. Airport (BOS) is one of the most popular airports in Wellesley. It's located 24 kilometers east of the downtown area. Other options open to you are T.F. Green Airport (PVD) (64 kilometers away from central Wellesley) and Manchester-Boston Regional Airport (MHT) (72 kilometers away from central Wellesley).
What is there to do in Wellesley?
Enjoy some great photo-ops at Wellesley College, one of the most well-known attractions in Wellesley. There's plenty more to discover in this exciting city, so make sure you have enough time to explore some off-the-beaten-path gems.
Where should I stay when visiting Wellesley?
Many travelers stay at the Wellesley Bed And Breakfast. It's a terrific base for your Wellesley escape.

Photos of local treasures

Browse Wellesley vacation photos for more inspiration

An aerial view of a snow-covered town with buildings, streets, and parked cars.
An aerial view of a beach surrounded by autumn-colored trees.
A church with a tall steeple, surrounded by autumn-colored trees and residential buildings.
A kitchen with shelves stocked with various kitchenware, including plates, bowls, and jars.
A lake with autumn-colored trees and two Adirondack chairs on the shore.

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