Wellesley Vacations from $1,045

Book a Hotel + Flight or Car together to unlock savings

Photo by Fun Travelog
Choose one or more items to build your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Wellesley Vacation

Lock in a Wellesley vacation package that has everything you need and nothing you don't. Good for shopping, markets and bars and pubs, consider staying in the neighborhood of East Cambridge. Every trip to Wellesley needs a well-planned itinerary. Fill yours with famous sights like Brandeis University, Wellesley College and Babson College. A couple of quick clicks is all it takes to craft a customized Wellesley vacation on Expedia.

The Latest Wellesley Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Great place, worth the money!

Reviewed on Jun 9, 2024

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
per person
Jul 24 - Jul 28
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
10/10 Exceptional! (4 reviews)
Everything was perfect

Reviewed on May 28, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 18 - Jul 21
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
EVERYTHING is thought out. Service is “old world”. Attention to details is magnificent. What’s there not to like.

Reviewed on Jun 9, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Great hotel. Very accommodating!

Reviewed on Jun 6, 2024

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
8.4/10 Very Good! (283 reviews)
The Nantucket Inn is a wonderful, romantic spot for visitors to the island. The pool is huge and beautifully decorated, as is the entire hotel. They provide a regular shuttle into town and to Surfside Beach. We couldn’t have enjoyed our stay more.

Reviewed on Jun 9, 2024

Wellesley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
28,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Boston Museum of Fine Arts, Museum of Science and Isabella Stewart Gardner Museum

Wellesley Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $178 per night from Jul 5 to Jul 6
$178
$236 total
includes taxes & fees
Jul 5 - Jul 6
9/10 Wonderful! (2,153 reviews)
"The room was very modern, stylish and comfortable."

Reviewed on Jun 4, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $171 per night from Jul 4 to Jul 5
$171
$234 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,702 reviews)
"From the time we valet the car, checked into room and got settled The whole process was so smooth. The staff from Valet to Fronk desk bellhop so courteous and a pleasure to talk too. Great location walking distance to a lot attractions and restaurants!!! This will be our go to spot going forward ..."

Reviewed on Jun 9, 2024

Omni Parker House
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $143 per night from Jul 7 to Jul 8
$143
$167 total
includes taxes & fees
Jul 7 - Jul 8
8.6/10 Excellent! (1,523 reviews)
"The location is very good. Billys Sub shop across the road is amazing. The loft rooms are just like having your own apartment. Amazing powerful shower."

Reviewed on Jun 7, 2024

The Revolution Hotel
See all 3,060 properties in Wellesley
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Wellesley vacation package cost?
Maybe less than you might think — from only $1,045, in fact! By combining flights, hotels and car rentals into your own tailor-made travel package, your getaway to Wellesley is just clicks away.
How do I get a cheap travel package to Wellesley?
Combine your hotel and flight bookings, toss in extras such as activities or a rental car, and save with a Wellesley vacation package. You won’t just score superb discounts on your trip — you’ll have lots of choice at your fingertips too. When you book with Expedia, you’ll have your pick of over 550 airlines and 1,000,000 hotels around the globe. Your dream vacation starts right here, right now!
Where should I stay in Wellesley?
A vacation in Wellesley isn’t complete without visiting Wellesley College, Babson College and Belkin Family Lookout Farm. Spend your evenings near these tourist attractions and make sightseeing simple.
What are the top hotels in Wellesley?
Travelers going to Wellesley often make a reservation at Spacious Private Entrance Master Bedroom or Wellesley Bed And Breakfast. These options are in Wellesley Hills. Another great neighborhood is Babson Park. Us Open Hse and Lovely Studio Walk To Wellesley And Babson College are recommended options in this area.
How far in advance should I book my Wellesley vacation?
It can be hard to know exactly when is the perfect time to book your Wellesley vacation. But generally the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels nearly 12 months before departure. If you’re considering a last-minute getaway, no need to worry! There are great deals posted on Expedia every single day.
What does an Expedia Wellesley travel package include?
Flights, rental cars and hotels — we have them covered. With Expedia, you can shape your Wellesley package however you want. All you have to do is figure out what you need. Once you’ve made your booking, you can add on fun things like activities and experiences. The more you bundle, the bigger your savings!
What should I know before booking a Wellesley travel package?
Locking in all the parts of your escape together is an excellent way to save. Combine your car rentals, airfares and hotels into a convenient little package. But it’s not just hotels. Expedia has all sorts of properties, including vacation rentals such as beachside villas and spacious residences. The list goes on!
Can I choose my airline with a Wellesley Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you sure can! Simply select your preferred carrier and put together your ideal Wellesley trip.
If I'm not able to travel, can I cancel my Wellesley vacation package?
Certainly, and we’ll help you every step of the way. You may be able to amend or cancel your Wellesley vacation package for free within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your vacation, visit our Customer Service Portal for more information.

Discover the most popular places to visit in Wellesley

Image for Fenway Park

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
Image for Harvard University

Harvard University

4.5/5(1,966 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Image for Gillette Stadium

Gillette Stadium

4.5/5(388 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

What to do in Wellesley

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

$30
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Freedom Trail: Small Group Tour of Revolutionary Boston

Freedom Trail: Small Group Tour of Revolutionary Boston

$39
Per adult
100% of travellers recommend
Freedom Trail: Small Group Tour of Revolutionary Boston
See all activities in Wellesley

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.