Milton Vacation Packages

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Your Milton Vacation

Book a Milton vacation package and get set to experience all this lively city has to offer. Consider staying in the neighborhood of Downtown Boston, which is good for nightlife, shopping and bars and pubs. South Shore Plaza, Blue Hills Ski Area and F1 Boston are just a few of the sights worth visiting during your trip to Milton. No matter your travel plans or the size of your budget, organizing a tailored Milton vacation is a breeze with Expedia.

Top Milton Vacation Deals

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

Lakeside Inn

2 out of 5
Price was CA $1,094, price is now CA $703 per person
CA $703
per person
Oct 29 - Nov 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,174 reviews)
Amazing full hot breakfast. Professional and friendly staff. Great quiet location with easy access.

Reviewed on Aug. 27, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,625, price is now CA $956 per person
CA $956
per person
Oct 31 - Nov 2
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (482 reviews)
Love the Street Bar!

Reviewed on Aug. 25, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,893, price is now CA $1,160 per person
CA $1,160
per person
Nov 3 - Nov 10
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
10 mins to Fenway - was a great place.

Reviewed on Aug. 27, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was CA $1,341, price is now CA $844 per person
CA $844
per person
Sep 27 - Oct 4
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
A simple but lovely place to stay!

Reviewed on Aug. 25, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Price was CA $1,728, price is now CA $1,163 per person
CA $1,163
per person
Oct 29 - Nov 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (139 reviews)
Clean. Great location.

Reviewed on Jul. 31, 2025

Ready to book your vacation to Milton?

 

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Milton Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Sep 1 to Sep 2
CA $223
CA $267 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,276 reviews)
"Clean comfortable room with massive comfy bed. Very conveniently situated for the cruise port. Staff were extremely professional, friendly and helpful."

Reviewed on Aug. 25, 2025

Seaport Hotel Boston
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 $295 per night from Sep 1 to Sep 2
CA $295
CA $400 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,870 reviews)
"We stayed for a couple of days at the end of our trip to Boston, the hotel was perfect for relaxing by the pool and a short walk from all the areas we wanted to see whilst visiting."

Reviewed on Aug. 25, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Sep 1 to Sep 2
CA $254
CA $295 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,709 reviews)
"So modern, clean and comfortable"

Reviewed on Aug. 27, 2025

citizenM Boston North Station
See all 3,730 properties in Milton
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 Milton

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 Milton

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
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 Milton

Frequently asked questions

How much does a Milton vacation package cost?
You can pick up a vacation package to this destination from CA $703 on Expedia. But how much your vacation to Milton costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Milton?
The off-season is the best time to head to Milton if you're hoping to keep costs down. Another tip for scoring cheap Milton vacation packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Milton?
Milton vacations come in many shapes and sizes, but to get a true feel for this place, we'd suggest 5 days is about right. In this timeframe, you can visit major attractions like Franklin Park Zoo and F1 Boston as well as lesser-known gems. Don't miss out on neighbourhoods such as South Boston and Dorchester either. If you're clever with your time, you can even schedule a day trip from Milton too.
Is it worth booking a vacation package to Milton?
It's no wonder a Milton vacation is on the to-do list of many travellers. Leading attractions like Blue Hills Reservation are just the start of what you can explore here.
How to find the best Milton package deals?
Start your search for a Milton package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Milton package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Milton escape underway.
Is it cheaper to book a Milton vacation as a package?
You can enjoy significant savings on your next Milton escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Milton?
If you're considering an impromptu Milton adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Milton?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Milton.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to experiences and flights. Your accommodations will likely be the largest expense during your trip to Milton.
  3. Determine how many days away: Start by making a list of all the attractions and activities you want to experience in Milton. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Milton vacation package.

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