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 Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Price was $516, price is now $384 per person
$384
per person
Feb 25 - Feb 28
found 9 hours ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 4 onsite conference rooms. A snack bar/deli and concierge services are also provided.
The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Price was $1,246, price is now $849 per person
$849
per person
Mar 7 - Mar 14
found 13 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Boston (BOS)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
The Hotel Salem

The Hotel Salem

3 out of 5
Downtown Salem
Save 100% on your flight
Price was $705, price is now $489 per person
$489
per person
Feb 1 - Feb 7
found 9 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A terrace, luggage storage, and concierge services are also on offer.
The Inn at Buzzards Bay

The Inn at Buzzards Bay

2.5 out of 5
Price was $903, price is now $669 per person
$669
per person
Mar 7 - Mar 14
found 13 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Boston (BOS)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-out, and barbecue grills are also on offer.
The Merchant

The Merchant

3 out of 5
Downtown Salem
Save 100% on your flight
Price was $851, price is now $632 per person
$632
per person
Feb 1 - Feb 7
found 9 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
This hotel features free WiFi in public areas, concierge services, and self parking. Enjoy the free on-the-go breakfast each morning. A terrace, a lobby fireplace, and a communal living room are also on offer.

Top Wellesley hotels deals

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$119 nightly
The price is $139 total per night
$139 total
Dec 29 - Dec 30
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
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
$167 nightly
The price is $195 total per night
$195 total
Dec 28 - Dec 29
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 business center and free WiFi in public areas. Self parking, express check-in, and express check-out are also offered.
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
$174 nightly
The price is $203 total per night
$203 total
Dec 26 - Dec 27
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
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$174 nightly
The price is $202 total per night
$202 total
Dec 26 - Dec 27
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
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $113 total per night
$113 total
Jan 1 - Jan 2, 2026
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
$395 nightly
The price is $460 total per night
$460 total
Jan 18 - Jan 19, 2026
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
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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 which includes a sporting event and night scenes as well as a large group of people

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
Boston Common featuring landscape views, a skyscraper and flowers

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
TD Garden

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

Frequently asked questions

How much are vacation packages to Wellesley?
Your vacation fantasies can become a reality in Wellesley from as little as $384. 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

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