
Middleton Vacation Packages
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Your Middleton Vacation
Book a custom vacation package to Middleton and get ready to experience this city however you like. Consider spending time in the neighborhood of Pine River Pond, which is great for fishing and much more. You'll want to do a little exploring during your trip to Middleton. Find time for popular attractions like Merrymeeting Lake, Sunrise Lake and Marchs Pond. Whoever you're taking time off with and whatever your budget, your dream Middleton vacation is just a few clicks away with Expedia.
Top Middleton Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Westin Boston Seaport District
Seaport District
Price was CA $1,072, price is now CA $747 per person
CA $747
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (2,398 reviews)
Excellent front desk staff. All staff were polite and welcoming and very helpful.
Clean spacious room.
Just wish the restaurabt offered a few simpler meal options
Reviewed on Apr 5, 2026

Eurostars The Boxer
West End
Price was CA $1,677, price is now CA $1,046 per person
CA $1,046
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Stayed 7 days. First day the door would not close and latch. Clearly a problem. It got fixed two days later. The location is great. Steps away from TD garden and North station. However, the property is clearly worn down and in need of updates. Also, they charge an amenity fee but there are no amenities to speak of. Getting tired of junk fees.
Reviewed on Apr 7, 2026

The Langham, Boston
Downtown Boston
Price was CA $2,613, price is now CA $1,663 per person
CA $1,663
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).
Reviewed on Apr 4, 2026

Boston Harbor Hotel
North End
Price was CA $3,314, price is now CA $2,169 per person
CA $2,169
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
From the moment we arrived we knew we made the right decision. The property is beautiful and the staff are professional and friendly. We were very pleased with our room and the great view of Boston Harbor. Two minor issues were the water spot on the bathroom sinks were too short for the size of the sink, making it hard to use without making a mess (wide designs such things and knows). The other minor item was the quality of the toilet tissue, for a hotel of this caliber, the need to spend a little more there. I must say that these were minor issues considering how amazing this property is. We went to the Dark Bar twice and loved it, had breakfast in the hotel restaurant and couldn’t have been more pleased and also had room service dinner one night and were very impressed. I would highly recommend this property!
Reviewed on Apr 6, 2026

Fairmont Copley Plaza, Boston
Back Bay
Price was CA $2,127, price is now CA $1,493 per person
CA $1,493
per person
May 31 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9/10 Wonderful! (1,212 reviews)
Very nice hotel that is centrally located. Close to the MFA, restaurants and shops. Enjoyed the rooftop gym. Staff was extremely courteous. There’s a mandatory food fee - it seems like more hotels are going that route these days.
Reviewed on Apr 6, 2026
Middleton Hotel Deals

Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Apr 30 to May 1
CA $146
CA $158 total
Apr 30 - May 1
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Yesss
Reviewed on Apr 2, 2026

Fireside Inn & Suites Gilford
17 Harris Shore Road Gilford NH
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Apr 15 to Apr 16
CA $202
CA $219 total
Apr 15 - Apr 16
includes taxes & fees
8.8/10 Excellent! (964 reviews)
It was the perfect choice for our family, pool and hot tub were awesome.
Reviewed on Mar 22, 2026

Homewood Suites by Hilton Dover
21 Members Way Dover NH
The price is CA $176 per night from Apr 21 to Apr 22
CA $176
CA $191 total
Apr 21 - Apr 22
includes taxes & fees
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.
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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.







