Milton Vacations from $467

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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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $819, price is now $467 per person
$467
per person
Dec 10 - Dec 12
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
8.4/10 Very Good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,538, price is now $889 per person
$889
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $894, price is now $631 per person
$631
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.2/10 Wonderful! (2,088 reviews)

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was $782, price is now $552 per person
$552
per person
Jan 6 - Jan 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
Great place to stay and relax. We enjoyed the ease of the grill and bar area . Also the closeness to downtown and all the history that Boston has to see .

Reviewed on Nov 2, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $2,003, price is now $1,435 per person
$1,435
per person
Jan 25 - Jan 29
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Great hotel and a great team

Reviewed on Nov 1, 2026

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Stay near popular Milton attractions

Pierce Reservation

Tucked along the Neponset River, this serene four-acre woodland offers a peaceful quarter-mile walk through grassy slopes. Access through Governor Hutchinson's Field for a brief escape into natural tranquility.
See properties

What to do in Milton

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$37
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
Museum of Ice Cream Boston Admission Ticket

Museum of Ice Cream Boston Admission Ticket

$44
per adult
80% of travellers recommend
Museum of Ice Cream Boston Admission Ticket
See all activities in Milton

Milton Hotel Deals

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
$200 nightly
The price is $233 total per night from Nov 22 to Nov 23
$233 total
Nov 22 - Nov 23
Total with taxes and fees
9.2/10 Wonderful! (4,975 reviews)
"Love his place. It’s my go to place whenever I got to Boston."

Reviewed on Nov 3, 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
$113 nightly
The price is $131 total per night from Nov 23 to Nov 24
$131 total
Nov 23 - Nov 24
Total with taxes and fees
The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $192 total per night from Nov 23 to Nov 24
$192 total
Nov 23 - Nov 24
Total with taxes and fees
9.6/10 Exceptional! (5,159 reviews)
"Clean room, friendly staff, and a comfy bed that made me question all my responsibilities back home. Lol Great location, great stay, and honestly, I wasn’t ready to check out!!!!"

Reviewed on Nov 3, 2026

Seaport Hotel Boston
See all 4,106 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 $467 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.

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