Milton Vacations from $376

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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.

The Latest Milton vacation packages

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

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $529, price is now $376 per person
$376
per person
Apr 29 - May 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (4,906 reviews)
Really good location and hotel

Reviewed on Mar 4, 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was $875, price is now $545 per person
$545
per person
May 16 - May 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Nothing to complain about!

Reviewed on Mar 1, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,317, price is now $899 per person
$899
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Friendly staff, clean room

Reviewed on Feb 20, 2026

The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Save 100% on your flight
Price was $888, price is now $607 per person
$607
per person
May 24 - May 28
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (253 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,036, price is now $724 per person
$724
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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Discover the most popular places to visit in Milton

Nighttime baseball game at Fenway Park showcasing a vibrant atmosphere in Boston, Massachusetts

Fenway Park

4.5/5(2,499 reviews)

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

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

4.5/5(388 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
Boston Common showcases lush greenery and city skyline under a clear blue sky during a sunny day

Boston Common

4.5/5(4,786 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 Milton

Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
100% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
See all activities in Milton

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
$157 nightly
The price is $182 total per night from Mar 8 to Mar 9
$182 total
Mar 8 - Mar 9
Total with taxes and fees
9.6/10 Exceptional! (4,031 reviews)
Very nice hotel. I would highly recommend it. It was accessible to many touristy options. It’s a quick walk to the Convention Center.

Reviewed on Mar 4, 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Mar 8 to Mar 9
$214 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (4,488 reviews)
Clean room, little small but is good

Reviewed on Mar 4, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
$158 nightly
The price is $184 total per night from Mar 22 to Mar 23
$184 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (3,117 reviews)
Yes

Reviewed on Mar 3, 2026

Hilton Boston Park Plaza
See all 4,210 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.

Find the Best Milton Vacation Packages

Milton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
27,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

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Frequently asked questions

How much does a Milton vacation package cost?
You can snap up a vacation package to this destination from $376 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?
You're likely to find lower rates and better availability in November, December and January. Browse our cheap Milton vacation packages and you could get some great off-season deals.
How many days is enough for Milton?
With a well-organized itinerary, you can easily visit the top Milton sights in a few days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Milton vacation for longer.
Is it worth booking a vacation package to Milton?
It's no wonder a Milton vacation is on the to-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. Choose your dates: The things you plan to do in Milton and your favorite season will help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will likely be the largest expense during your trip to Milton.
  3. Use Expedia's trip planning tool to explore Milton: Research every part of your trip to Milton with this handy planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Set the duration of your trip: Start by listing all the sights and activities you want to get to in Milton. Then, estimate how long you'll need for each, along with any travel time.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Milton vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some incredible things to do in Milton. Book tickets or make reservations in advance to save time and avoid the stress of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Milton vacation packages?
Your Milton trip should be an escape from your busy life, not a reason for money worries. So to give you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Explore a world of travel with Expedia

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