Book Exclusive Wellesley Vacation Packages

Choose one or more items to build your trip:

Wellesley flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
Coolidge Corner
Price was CA $1,358, price is now CA $997 per person
CA $997
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was CA $1,914, price is now CA $1,274 per person
CA $1,274
per person
Oct 15 - Oct 20
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hyannis Harbor and Cape Cod Inflatable Park are located nearby.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Price was CA $2,050, price is now CA $1,372 per person
CA $1,372
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $2,528, price is now CA $1,816 per person
CA $1,816
per person
Oct 15 - Oct 20
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Nobadeer Beach and Madequecham Pond are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was CA $2,097, price is now CA $1,530 per person
CA $1,530
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.

Top Wellesley hotels deals

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 $263 per night
CA $263
CA $354 total
Aug 30 - Aug 31
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 Faneuil Hall Marketplace 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
The price is CA $189 per night
CA $189
CA $220 total
Aug 23 - Aug 24
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
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 $326 per night
CA $326
CA $437 total
Aug 27 - Aug 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 Faneuil Hall Marketplace are located nearby.
Pool
Hot tub
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $275 per night
CA $275
CA $368 total
Aug 30 - Aug 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
Pet-friendly
Free WiFi
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Free cancellation
Reserve now, pay when you stay
The price is CA $262 per night
CA $262
CA $305 total
Aug 16 - Aug 17
includes taxes & fees
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.
Breakfast included
Pet-friendly
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $249 per night
CA $249
CA $289 total
Aug 16 - Aug 17
includes taxes & fees
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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
Free WiFi
Restaurant
Don't see what you're looking for?
See all available properties in Wellesley
View all properties
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 $997. 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.

Explore More Ways to Travel with Travelocity