Deals on vacations and trips to Wellesley

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Wellesley flight + hotel vacation packages

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

The Arcadian Hotel

3.5 out of 5
Coolidge Corner
Price was $590, price is now $434 per person
$434
per person
Apr 22 - Apr 26
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
A 24-hour gym is featured at this hotel, along with self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage storage is provided and the front desk is staffed around-the-clock.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,364, price is now $1,412 per person
$1,412
per person
Apr 22 - Apr 26
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was $815, price is now $553 per person
$553
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the seasonal outdoor pool, poolside bar, and laundry facilities.
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Save 100% on your flight
Price was $811, price is now $587 per person
$587
per person
Apr 19 - Apr 22
found 8 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
A gym is featured at this hotel, along with self parking. WiFi in public areas is free. Traveling for business? Take advantage of the business center, express check-in, and conference center.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was $885, price is now $659 per person
$659
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel features free WiFi in public areas, laundry facilities, and self parking. Enjoy the free buffet breakfast each morning. A computer station and luggage storage are also provided.

Top Wellesley hotels deals

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$109 nightly
The price is $127 total per night
$127 total
Feb 16 - Feb 17
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.
Free WiFi
Restaurant
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $112 total per night
$112 total
Feb 17 - Feb 18
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.
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
$365 nightly
The price is $425 total per night
$425 total
Feb 19 - Feb 20
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Pool
Pet friendly
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$148 nightly
The price is $173 total per night
$173 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A coffee shop, a communal living room, and a library are also on offer.
Pet friendly
Free WiFi
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $152 total per night
$152 total
Feb 22 - Feb 23
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the steam room, bar/lounge, and concierge services.
Pool
Pet friendly
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
$146 nightly
The price is $170 total per night
$170 total
Feb 16 - Feb 17
Total with taxes and fees
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.
Pool
Hot Tub
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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

Boston Common featuring a garden and a pond as well as a small group of people

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common
Boston's Zakim Bridge

TD Garden

4.5/5(1,780 reviews)

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
Fenway Park showing a sunset and signage

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park

Frequently asked questions

How much are vacation packages to Wellesley?
Your vacation fantasies can become a reality in Wellesley from as little as $434. 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 40 mi from Wellesley.
Which airport is best for Wellesley?
Logan Intl. Airport (BOS) is one of the most popular airports in Wellesley. It's located 15 mi east of the downtown area. Other options open to you are T.F. Green Airport (PVD) (40 mi away from central Wellesley) and Manchester-Boston Regional Airport (MHT) (45 mi 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

Aerial view of Wellesley, Massachusetts in winter
Aerial view of Wellesley, Massachusetts in winter
Pine Straw is great new store filled with french home accessories, cookbooks, jewelry ... Everything good!!!
Never knew that Wellesley College campus had such a picturesque sitting spot available 😍😍 Getting to know our neighboring towns this Sunday. How was your weekend?