Middleton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Your Middleton Vacation

Say bye-bye to planning worries and hello to a Middleton vacation package. With your travel details organized before you take off, you can focus on discovering this city, starting with Ballardvale, which is good for watersports, nature and history. Any trip to Middleton needs a well-crafted itinerary. Fill yours with famous sights like Water Park of New England, MarketStreet Lynnfield and Glen Magna Farms. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Middleton vacation is easy with Expedia.

Top Middleton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Sep 4 - Sep 8
found 22 hours ago
Roundtrip non-stop 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

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
per person
Sep 25 - Sep 28
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
It was a pleasant stay. The staffs were friendly. The room had both microwave and fridge. Although the room was neat, the cleaners did miss a couple of things.

Reviewed on Jun. 29, 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
Sep 25 - Sep 30
found 23 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

Ready to book your vacation to Middleton?

 

Choose your dates

Middleton Hotel Deals

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 $289 per night from Aug 10 to Aug 11
CA $289
CA $393 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,667 reviews)
"The hotel was clean and staff was friendly."

Reviewed on Jul. 12, 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 $252 per night from Jul 13 to Jul 14
CA $252
CA $293 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,408 reviews)
"Always a great stay"

Reviewed on Jul. 11, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is CA $282 per night from Jul 13 to Jul 14
CA $282
CA $329 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (5,302 reviews)
"this property was perfect for our stay in Bostain. First of all the room was large, clean and very comfortable. The front desk staff was very pleasant. The best part about this hotel is the location. You are on the waterfront and within walking distance of everything you need including many tours. ..."

Reviewed on Jul. 10, 2025

Harborside Inn Of Boston
See all 4,099 properties in Middleton
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 Middleton

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 Middleton

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 Middleton

Frequently asked questions

How much does a Middleton vacation package cost?
Offering excellent value package deals from CA $819 on Expedia, you'll be pleasantly surprised at how much a vacation to Middleton costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Middleton?
January, February and November are the best times to search for cheap Middleton vacation packages. Travelling in quieter periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Middleton?
Typically, a handful of days is enough to visit the major attractions during your Middleton vacation. But if you'd like to have some time to unwind or go on day trips, consider extending your trip.
How to find the best Middleton package deals?
Use Expedia's filter tool to help you find some unbeatable Middleton 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 escape for midweek, or search for Middleton package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Middleton vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Middleton vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Middleton?
If you're planning an impromptu Middleton vacation, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Middleton?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Middleton.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to experiences and flights. Your hotel will likely be the biggest expense during your trip to Middleton.
  3. Determine how many days away: Start by making a list of all the attractions and activities you want to experience in Middleton. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Middleton vacation package that brings all your bookings together.

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