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 Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was CA $924, price is now CA $747 per person
CA $747
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, 3 restaurants, 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,032, price is now CA $1,292 per person
CA $1,292
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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 New England Aquarium and Boston Common are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $1,759, price is now CA $1,248 per person
CA $1,248
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $1,318, price is now CA $972 per person
CA $972
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
Fenway–Kenmore
Price was CA $1,016, price is now CA $820 per person
CA $820
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.

Top Wellesley hotels deals

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Get rates
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
Free WiFi
Restaurant
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $193 per night
CA $193
CA $266 total
Dec 28 - Dec 29
includes taxes & fees
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Free WiFi
Restaurant
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 $190 per night
CA $190
CA $277 total
Dec 27 - Dec 28
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 New England Aquarium 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 $231 per night
CA $231
CA $276 total
Dec 29 - Dec 30
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 New England Aquarium 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
Free cancellation
Reserve now, pay when you stay
Get rates
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
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $540 per night
CA $540
CA $629 total
Jan 18 - Jan 19, 2026
includes taxes & fees
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 clean rooms in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
Pool
Pet-friendly
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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.

Popular places to visit

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

Fenway Park

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Boston Common which includes flowers, a garden and landscape views

Boston Common

After visiting Boston Common, make a plan to see the other sights and activities in Boston. Discover the fascinating museums in this vibrant area, or seek out the local tours.

Boston Common
TD Garden

TD Garden

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

TD Garden

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 $747. 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

Photo by Fun Travelog
Photo by Fun Travelog
Photo by Lisa Frackiewicz
Photo by Lisa Frackiewicz