Wakefield Vacation Packages

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Your Wakefield Vacation

From its rich history to its cultural experiences and spectacular views, you'll find tons of good reasons to spend time in the rural city of Wakefield. Experience all this and more when you lock in your vacation package to Wakefield. MarketStreet Lynnfield, Woburn Mall and Square One Mall are just a few of the many sights worth visiting during your trip to Wakefield. Stop dreaming and start traveling. Explore the many options on Expedia today and finally put your Wakefield vacation plans into motion!

Top Wakefield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,056 reviews)
Was actually too nice for us

Reviewed on Jul. 1, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Save 100% on your flight
per person
Aug 17 - Aug 24
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (135 reviews)
Nobody on property to talk to

Reviewed on May 20, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Sep 19 - Sep 22
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
fabulous everything!

Reviewed on Jul. 2, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (224 reviews)
We loved our stay here! Very nice and convenient to cute stores and restaurants

Reviewed on Jun. 29, 2025

Ready to book your vacation to Wakefield?

 

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Wakefield Hotel Deals

Lakeside Inn
Lakeside Inn
2 out of 5
595 North Ave, Wakefield, MA
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Jul 13 to Jul 14
CA $125
CA $140 total
Jul 13 - Jul 14
includes taxes & fees
7.2/10 Good! (2,178 reviews)
"Good location and very private"

Reviewed on Jul. 3, 2025

Lakeside Inn
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $325 per night from Aug 7 to Aug 8
CA $325
CA $434 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (3,629 reviews)
"The hotel was gorgeous! But I booked this hotel over the others for the outdoor pool only to get there and be told that I needed to have mad reservations for the pool. It was so disappointing. I wish I was sent any kind of notification when I booked."

Reviewed on Jul. 6, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $250 per night from Jul 13 to Jul 14
CA $250
CA $291 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,367 reviews)
"Wonderful hotel!"

Reviewed on Jul. 5, 2025

citizenM Boston Back Bay
See all 3,753 properties in Wakefield
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

Family Vacations

Family Vacations

Discover the most popular places to visit in Wakefield

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 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
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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

What to do in Wakefield

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $75
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Wakefield

Frequently asked questions

How much does a Wakefield vacation package cost?
You can snap up a vacation package to this top destination from CA $703 on Expedia. But how much your vacation to Wakefield costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Wakefield?
December, January and February are great times to search for cheap Wakefield vacation packages. Travelling in less busy months means you can usually find lower prices on accommodations and flights.
How many days is enough for Wakefield?
Usually, a handful of days is great for a Wakefield vacation. With a well-organized schedule, you can go to all the popular sights including Middlesex Fells Reservation, as well as discover some hidden treasures along the way.
How to find the best Wakefield package deals?
Use Expedia's filter tool to find some tempting Wakefield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Wakefield package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Wakefield vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Wakefield trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Wakefield?
If you're planning an impromptu Wakefield vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Wakefield?

  1. Pick your dates: The things you plan to do in Wakefield and your favourite season can help you decide when to get away.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Wakefield.
  3. Work out your trip length: Think about how long you want to spend exploring Wakefield. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Wakefield vacation package.

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