Milton Vacations from $1,013

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • 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.

The Latest Milton vacation packages

Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,755, price is now $1,013 per person
$1,013
per person
Sep 25 - Sep 28
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $2,321, price is now $1,308 per person
$1,308
per person
Sep 3 - Sep 10
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,463, price is now $1,463 per person
$1,463
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on Jul 11, 2026

The Coach House

The Coach House

3 out of 5
Save 100% on your flight
Price was $1,891, price is now $1,178 per person
$1,178
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (182 reviews)
This experience was amazing! We loved every detail. It was so trendy and dapper yet held the boldness with such grace. It was lovely. The room had everything to make your stay comfortable. There was coffee and teas and fresh water. We found this refreshing on the hot summer day that we were there. The beds were so nice. The snacks and robes were a great touch. We loved reading about the history and just adored everything.

Reviewed on Jul 11, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $2,310, price is now $1,469 per person
$1,469
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.

Reviewed on Jul 12, 2026

Don't see what you're looking for?
See all available trips from Columbus to Milton
View all trips

Stay near popular Milton attractions

Eustis Estate Museum and Study Center

You can spend an afternoon studying the exhibits at Eustis Estate Museum and Study Center in Milton. While you're in the area, wander around the natural setting.
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
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

$47
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston Summer Nights Tour

Boston Summer Nights Tour and River Cruise

$50
per adult
100% of travellers recommend
Boston Summer Nights Tour and River Cruise
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
$219 nightly
The price is $254 total per night from Jul 26 to Jul 27
$254 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (4,576 reviews)
"Excellent property!!"

Reviewed on Jul 12, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $177 total per night from Aug 2 to Aug 3
$177 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (2,738 reviews)
"So this was my first foray into a shared bathroom, and it was actually super easy and not at all an issue. What was an issue was that when a hall shares a bathroom, doors are opening and closing all night, and the doors snapped shut very loudly. If you are a very light sleeper, I don't think this ..."

Reviewed on Jul 12, 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $181 total per night from Aug 9 to Aug 10
$181 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (2,445 reviews)
"Great location to Boston especially if you are touring Harvard, MIT, Northeastern, or BU. Hotel is clean and the gym is great and the staff is friendly."

Reviewed on Jul 13, 2026

Hyatt Regency Boston/Cambridge
See all 4,197 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Milton vacation package cost?
You can snap up a vacation package to this destination from $1,013 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.