Wellesley Vacations from $629

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Your Wellesley Vacation

Reserve a Wellesley vacation package and prepare to experience everything this city has to offer. Consider staying in the neighborhood of East Cambridge, which is good for shopping, markets and bars and pubs. If your trip to Wellesley includes a little sightseeing, take in renowned attractions like Wellesley College, Brandeis University and Babson College. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Wellesley now.

The Latest Wellesley vacation packages

Price found within the past 48 hours. Click for updated prices.
The Groton Inn

The Groton Inn

3.5 out of 5
Save 100% on your flight
Price was $1,022, price is now $629 per person
$629
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (500 reviews)
The rooms are large and comfortable. The property is very well maintained and the porch is lovely.

Reviewed on Apr 26, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,504, price is now $1,537 per person
$1,537
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
clean and great staff

Reviewed on May 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,154, price is now $1,324 per person
$1,324
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Right in heart of town

Reviewed on May 12, 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was $1,260, price is now $798 per person
$798
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
Friendly staff clean room good location

Reviewed on May 14, 2026

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

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

3 out of 5
Save 100% on your flight
Price was $4,395, price is now $2,940 per person
$2,940
per person
Jul 23 - Jul 27
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

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Discover the most popular places to visit in Wellesley

Fenway Park

Fenway Park

4.5/5(2,543 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(1,983 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
Gillette Stadium

Gillette Stadium

4.5/5(400 reviews)

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

Gillette Stadium

What to do in Wellesley

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
See all activities in Wellesley

Wellesley Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$286 nightly
The price is $332 total per night from May 25 to May 26
$332 total
May 25 - May 26
Total with taxes and fees
9.6/10 Exceptional! (4,340 reviews)
The only hiccup we had was a less than helpful staff at the restaurant for dinner. after a brief “discussion” things changed and we had a good meal.

Reviewed on May 13, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $167 total per night from May 25 to May 26
$167 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (2,603 reviews)
This was such a fun location and a great way for people to share a room and save some money in downtown Boston. We loved the experience, the hotel, and the staff. 10/10. Would stay here again!

Reviewed on May 11, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $235 total per night from May 29 to May 30
$235 total
May 29 - May 30
Total with taxes and fees
9.2/10 Wonderful! (4,667 reviews)
This is one of the best decisions I ever made honestly!! They were all so sweet. The hotel was gorgeous and I had written a note for them before coming that it was my birthday and if I could get the highest floor. They had 22 floors and gave me the 20th and not just that but they also had a cup desert ...

Reviewed on May 13, 2026

Omni Boston Hotel at the Seaport
See all 3,961 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.

Find the Best Wellesley Vacation Packages

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

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Frequently asked questions

How much does a Wellesley vacation package cost?
You can snap up a vacation package to this top destination from $629 on Expedia. But how much your vacation to Wellesley costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Wellesley?
You can usually find reduced prices and better availability in November, December and January. Take a look at our cheap Wellesley vacation packages and you could score some great off-season discounts.
How many days is enough for Wellesley?
The ideal length of your Wellesley vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to hit all the major sights and explore some hidden spots along the way.
How to find the best Wellesley package deals?
Bagging a cheap Wellesley package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Wellesley package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Wellesley vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights separately. Better still, you can tailor your Wellesley escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Wellesley?
If you're planning an impromptu Wellesley getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Wellesley vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Wellesley vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.

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