Middleton Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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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.

Top Middleton Vacation Deals

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

Boston Harbor Hotel

5 out of 5
North End
per person
Jul. 2 - Jul. 5
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
This is an upscale hotel with excellent amenities and wonderfully helpful and friendly people who kindly made our stay a joy.

Reviewed on May 27, 2024

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Jul. 2 - Jul. 5
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (3,317 reviews)
Very clean and staff was approachable.

Reviewed on May 29, 2024

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jul. 2 - Jul. 5
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (153 reviews)
From the moment we walked into the lobby at Beacon Hill Hotel we were greeted and treated like VIPs. The room, was a corner, looking out over Charles Street. Perfectly comfortable and artfully appointed. My only complaint and this is silly the pillows too puffy. We dined there as well and the food and service was superb.

Reviewed on May 23, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 2 - Jul. 5
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (270 reviews)
Awesome, awesome, awesome. I could not find another word to describe my stay! Awesome.

Reviewed on May 22, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 2 - Jul. 5
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (31 reviews)
Beautiful hotel, flowers in All areas. Staff was superb. Two very minor issue - no fan for toilet area, hot water in shower takes a bit. Doesn’t distract from my overall rating. Easily a come back recommendation

Reviewed on May 29, 2024

Middleton Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $355 per night from Jun. 23 to Jun. 24
CA $355
CA $453 total
includes taxes & fees
Jun 23 - Jun 24
9/10 Wonderful! (2,097 reviews)
"Wowowow I cannot say enough good things about our stay. Not only is the hotel itself gorgeous, but the staff were absolutely lovely as well. They were so kind and accommodating, our every interaction with staff was a delight. The hotel is filled with beautiful art pieces adding to the amazing ambiance. ..."

Reviewed on May 27, 2024

Omni Boston Hotel at the Seaport
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 $367 per night from Jun. 16 to Jun. 17
CA $367
CA $434 total
includes taxes & fees
Jun 16 - Jun 17
9.6/10 Exceptional! (2,181 reviews)
Two Thumbs Up
"Great place to stay and lots to do around the hotel. I was there for the Run to Remember Boston Run. Perfect spot to stay at."

Reviewed on May 28, 2024

Seaport Hotel Boston
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $303 per night from Jun. 16 to Jun. 17
CA $303
CA $401 total
includes taxes & fees
Jun 16 - Jun 17
8.8/10 Excellent! (2,669 reviews)
"Historic property in a fantastic location. Our basic king room was small but clean, quiet, and comfortable. The staff were fantastic."

Reviewed on May 27, 2024

Omni Parker House
See all 3,603 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Middleton vacation package cost?
Our Middleton vacation packages, which start from just CA $935, are an easy way to save precious money. All you have to do is choose your favorite hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Middleton?
Our Middleton vacation packages promise plenty of savings for the savvy traveler. For the best deals, simply bundle your flights, hotels and rental cars into a convenient package. But bargain prices are just the beginning of your next epic adventure. When you book with Expedia, you’ll have more than 550 airlines and 1,000,000 hotel options worldwide to choose from. No matter your budget, there’s a package that’s perfect for you.
Where should I stay in Middleton?
Middleton features numerous top places to see, such as Sagamore Spring Golf Club. Secure a room in a hotel close by and make sightseeing simple.
How far in advance should I book my Middleton vacation?
Savvy travelers often book early. You can normally start comparing international airfares on Expedia up to 12 months before your flight. If you’re purchasing tickets last minute, there’s no need to worry. Cheap prices occasionally occur just weeks before departure dates.
What does an Expedia Middleton travel package include?
Much of that depends on you. You can select from a range of Middleton bundles, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a rental car with a flight. Once you’ve made your booking, you can add on the fun stuff like activities and tours. Whatever your dream Middleton trip looks like, get set to save!
What should I know before booking a Middleton travel package?
When you book your flights, hotels and car rentals together, you’ll score amazing discounts. Whether you’re organizing a beach escape in a villa or would rather stay in an upscale city hotel, Expedia will make it happen for less.
Can I choose my airline with a Middleton Expedia vacation package?
With a vacation package, you’re in charge. Whether you want to fly to Middleton in economy or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners across the world.
If I'm not able to travel, can I cancel my Middleton vacation package?
It’s hard to predict what tomorrow might bring, so it’s comforting to know that you can change or cancel your Middleton vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.

Discover the most popular places to visit in Middleton

Image for Fenway Park

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
Image for Harvard University

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
Image for Boston Common

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

What to do in Middleton

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

CA $41
Per adult
100% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $264
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Middleton
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.