Middleton Vacations from $455

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Your Middleton Vacation

Say bye-bye to planning worries and hello to a Middleton vacation package. With your travel details organized before you take off, you can focus on discovering this city, starting with Ballardvale, which is good for watersports, nature and history. Any trip to Middleton needs a well-crafted itinerary. Fill yours with famous sights like Water Park of New England, MarketStreet Lynnfield and Glen Magna Farms. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Middleton vacation is easy with Expedia.

The Latest Middleton vacation packages

Price found within the past 48 hours. Click for updated prices.
Josiah Keith House

Josiah Keith House

2 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 19
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (19 reviews)
The inn keeper was available at all times and very attentive to our stay. The history of the home given by the inn keeper was interesting and informative. Highly recommend.

Reviewed on Jun 24, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,999 reviews)
This is a great place for a quick layover in Boston. There is a family owned Italian pizzeria/bar a short walk away (Santarpio’s). It’s a great place to hang out and have a great pizza! The free shuttle to/from the airport is very nic

Reviewed on Jul 9, 2025

Holly Tree Resort

Holly Tree Resort

3 out of 5
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (344 reviews)
Love the pools and how close it is to everything , it’s literally in the center of the cape so even a ride to Provincetown is only a little over a hour, the room was big with two bathrooms, air conditioning worked great nice little barbecue area with basketball court and playground and the front desk had no problem helping with anything we will continue to make this a every summer destination for years to come

Reviewed on Jul 6, 2025

Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
7.8/10 Good! (715 reviews)
Staff was great very helpful, and it is family friendly.

Reviewed on Jul 5, 2025

Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
7.6/10 Good! (374 reviews)
It’s a great resort! Especially for your kids! They have a park! The only thing is, it gets very muddy. The rooms are good but need a dehumidifier because everything feels wet. Would stay there again beaches are very close!

Reviewed on Jul 7, 2025

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Discover the most popular places to visit in Middleton

Fenway Park which includes a sporting event and night scenes as well as a large group of people

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
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(1,966 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
Boston Common featuring landscape views, a skyscraper and flowers

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 Middleton

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$70
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

$25
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
See all activities in Middleton

Middleton Hotel Deals

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
$274 nightly
The price is $319 total per night from Aug 7 to Aug 8
$319 total
Aug 7 - Aug 8
Total includes taxes and fees
9/10 Wonderful! (3,651 reviews)
"We just had a wonderful stay at the Omni seaport ! It was July 4th weekend so it was. Busy but still the hotel was very attentive and organized . From valet to front desk , to the pool staff everyone was friendly and helpful and also had in room dining for breakfast from kestra ans it was amazing ..."

Reviewed on Jul 8, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Jul 13 to Jul 14
$214 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (1,373 reviews)
"First time there. Wanted something walkable to Fenway Park. Definitely unique. I had a smaller room. It was fine for me, but didn’t like the bed totally against the wall. Wish it had makings for simple coffee in am instead of going downstairs. Would have liked a hot tub too. But I would go back"

Reviewed on Jul 6, 2025

citizenM Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $181 total per night from Jul 20 to Jul 21
$181 total
Jul 20 - Jul 21
Total includes taxes and fees
8.4/10 Very Good! (3,720 reviews)
"Nicely appointed room, very quiet. Appreciated the comlimentary bottled waters, and a fridge/freezer!!!"

Reviewed on Jul 9, 2025

Copley Square Hotel, a FOUND Hotel
See all 4,097 properties in Middleton
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 Middleton Vacation Packages

Middleton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
9,900
Max Temp Winter
35ºF
Max Temp Summer
75ºF
Top Sights
Marblehead Museum & Historical Society, Ski Bradford and Gas House Beach

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Frequently asked questions

How much does a Middleton vacation package cost?
You'll find cheap prices from $455 on Expedia for your Middleton escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Middleton costs.
What are the cheapest months to go to Middleton?
If you're looking to score a cheap Middleton vacation package, consider visiting in November, December and January. You'll typically find lower prices on airfares and hotels during these quieter months --- ideal for a budget-friendly getaway.
How many days is enough for Middleton?
The ideal duration for your Middleton vacation depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to visit all the major attractions and discover some hidden gems along the way.
How to find the best Middleton package deals?
Bagging a cheap Middleton package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Middleton package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Middleton vacation as a package?
You can enjoy significant savings on your next Middleton escape by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Middleton?
If you have your Middleton travel dates finalized, book as early as you can to score some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Middleton vacation packages?
Your Middleton trip is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.