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.
Lakeside Inn

Lakeside Inn

2 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
7.4/10 Good! (2,171 reviews)
Staff was very friendly and room was clean. Bathroom was very outdated but clean

Reviewed on Aug. 4, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug. 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug. 5, 2025

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
7/10 Good! (157 reviews)
There were a few places to eat near the pier the view of the city was amazing and the tall boat was great for food,dancing and drinking however the vibe is younger college kids. I did enjoy the few places we visited to eat. The parking was horrible, We received no directions and it took us an hour to find someone to check in… I was left with two keys and no directions. I managed and once the sun came up an employee at the front desk named Craig was very helpful. The bed was so uncomfortable I would recommend getting a new more comfortable mattress for the amount we paid. All in all we made the best of it and everything else was okay. Lastly no TV directions I had to purchase Netflix on my own. This was not the best stay provided by Expedia. I was disappointed.

Reviewed on Jul. 31, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 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 $133 per night from Aug 11 to Aug 12
CA $133
CA $148 total
Aug 11 - Aug 12
includes taxes & fees
7.4/10 Good! (2,158 reviews)
"Staff was very friendly and room was clean. Bathroom was very outdated but clean"

Reviewed on Aug. 4, 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 $252 per night from Aug 24 to Aug 25
CA $252
CA $349 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,784 reviews)
Decent Size Studio Rm, can get noisy from planes
"I stayed at the Artist Studio Tower, which faces the East and North I think. The room itself was thoughtfully designed to utilize limited space for comfort, and looked nice and luxurious. However, there wasn't any dedicated desk for working on a laptop (Just a small stand for a coffee machine and ..."

Reviewed on Aug. 7, 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Sep 1 to Sep 2
CA $221
CA $313 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (3,206 reviews)
Wonderfully Stay
"We thoroughly enjoyed our stay! The staff was friendly, so very helpful in what we asked, was just a wonderful experience!"

Reviewed on Aug. 5, 2025

Hilton Boston Park Plaza
See all 3,754 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
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Family Vacations
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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

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

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

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
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
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

CA $115
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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 $512 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.