Middleton Vacation Packages
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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 Lodge and Suites
Dorchester
Price was CA $1,179, price is now CA $766 per person
CA $766
per person
Jul 17 - Jul 19
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.
Reviewed on Nov 10, 2025
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,961, price is now CA $1,225 per person
CA $1,225
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (187 reviews)
It’s a cute little place right on the ocean with its own beach.
Reviewed on Jun 12, 2026
The Atlas Hotel
Allston
Price was CA $1,273, price is now CA $832 per person
CA $832
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (125 reviews)
Exceptional service at the Atlas Hotel
Very clean facilities with service oriented staff members who are always willing to help and they go the extra mile to get things done.
Particularly thanks to Damion for the quick check in process and the very nice gift left in my room upon arrival. Very thoughtful gesture.
The Coop store in the hotel has the most beautiful items.
The Atlas is a must visit hotel. And did I mention that it is just right across from the Harvard Business School.
Reviewed on Jun 14, 2026
Chatham Tides
Price was CA $2,536, price is now CA $1,700 per person
CA $1,700
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (701 reviews)
Beautiful place! Beach was right outside our door, staff was excellent, room was clean! Definitely will be visiting again!
Reviewed on Jun 14, 2026
Middleton Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Jul 2 to Jul 3
CA $267
CA $368 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (4,730 reviews)
"Can hear everything in the hallways from room."
Reviewed on Jun 14, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Jul 5 to Jul 6
CA $200
CA $233 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (2,690 reviews)
"Amazing location. Staff was professional. Bed was massive. Great view of downtown from my window. Would stay here again for sure."
Reviewed on Jun 14, 2026
The Godfrey Hotel Boston
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $327 per night from Jun 21 to Jun 22
CA $327
CA $438 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (5,112 reviews)
"Great spot, and great location. Would definitely stay again!"
Reviewed on Jun 14, 2026
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.
Stay near popular Middleton attractions
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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.
