Milton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9/10 Wonderful! (203 reviews)
The staff was excellent and sought to solve any problem or question on the spot. The hotel and bar had a fun and fresh vibe. I liked the room decor and cleanliness although my room was small. I would stay here again because of location and amazing staff.

Reviewed on Mar. 31, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,011 reviews)
This is a wonderful property that truly felt like a home away from home. The service and amenities were spectacular. The hotel was very quiet and relaxing. I will definitely return in the future.

Reviewed on Apr. 3, 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
Jun. 10 - Jun. 15
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Boston (BOS)
9.6/10 Exceptional! (234 reviews)
Beautiful accommodations and unique character

Reviewed on Nov. 6, 2024

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
per person
Jun. 10 - Jun. 15
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Boston (BOS)
9.2/10 Wonderful! (1,001 reviews)
Always a pleasure staying at the Charles.

Reviewed on Mar. 27, 2025

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
7.4/10 Good! (525 reviews)
The air conditioner is too loud.

Reviewed on Mar. 31, 2025

Ready to book your vacation to Milton?

 

Choose your dates

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 $400 per night from May 4 to May 5
CA $400
CA $473 total
includes taxes & fees
May 4 - May 5
9.4/10 Exceptional! (2,873 reviews)
"Great stay and service"

Reviewed on Apr. 4, 2025

Seaport Hotel Boston
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 $245 per night from Apr. 13 to Apr. 14
CA $245
CA $285 total
includes taxes & fees
Apr 13 - Apr 14
9.4/10 Exceptional! (941 reviews)
"Ricky at the front desk was amazing and super helpful! 5 star service!"

Reviewed on Apr. 2, 2025

citizenM Boston Back Bay
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Apr. 6 to Apr. 7
CA $252
CA $293 total
includes taxes & fees
Apr 6 - Apr 7
8.6/10 Excellent! (1,982 reviews)
"Stayed in a Lofts suite, which was excellent for us. The staff at the front desk were nice and very helpful."

Reviewed on Apr. 3, 2025

The Revolution Hotel
See all 3,683 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

Frequently asked questions

How much does a Milton vacation package cost?
You can snap up a vacation package to this destination from CA $960 on Expedia. However, how much your vacation to Milton costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Milton?
Travel in the off-peak season and you’re likely to get cheap Milton vacation packages. Keep in mind that school vacation periods and major events and festivals can impact prices, so do a little research before you go.
How many days is enough for Milton?
The ideal length of your Milton vacation depends on what you’d like to see and do. Typically, a handful of days to a week will give you enough time to hit all the main sights and discover some hidden gems along the way.
Is it worth booking a vacation package to Milton?
It’s no wonder a Milton vacation is on the must-do list of many travelers. Leading attractions like Blue Hills Reservation are just the start of things to see and do here.
How to find the best Milton package deals?
Use Expedia’s filter tool to help you find some tempting Milton package deals. When you start your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Milton 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 Milton vacation as a package?
You can enjoy significant savings on your Milton retreat by booking a personalized vacation package. Check the “Package” heading, then enter your travel dates and destination to view some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Milton?
If you’re considering a spur-of-the-moment Milton trip, 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 land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Milton?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to visit Milton.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and flights. Your hotel will likely be the biggest expense during your trip to Milton.
  3. Decide how long to go for: Now that you’re up to speed on Milton, you can work out the ideal length of your break. Put together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that’s left is to pick a Milton vacation package that brings all your bookings together.

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

4.5/5(305 reviews)

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

Fenway Park
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
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

What to do in Milton

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $113
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 $36
per adult
80% 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 $106
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Milton
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.