
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 Colonnade Hotel Back Bay
Back Bay
Price was CA $1,152, price is now CA $800 per person
CA $800
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..
Reviewed on Feb 2, 2026

Boston Harbor Hotel
North End
Price was CA $3,075, price is now CA $1,643 per person
CA $1,643
per person
Apr 29 - May 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on Jan 25, 2026

The Langham, Boston
Downtown Boston
Price was CA $1,582, price is now CA $1,072 per person
CA $1,072
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you
Reviewed on Feb 3, 2026

Mandarin Oriental, Boston
Back Bay
Price was CA $4,722, price is now CA $3,272 per person
CA $3,272
per person
Mar 30 - Apr 5
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Boston (BOS)
9.4/10 Exceptional! (376 reviews)
The rooms are spotless , staff are extremely welcoming. Everything and more you could want while staying in Boston
Reviewed on Feb 8, 2026

The Whitney Hotel
Beacon Hill
Price was CA $1,426, price is now CA $1,005 per person
CA $1,005
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.
Reviewed on Feb 7, 2026
Middleton Hotel Deals

Fireside Inn & Suites Gilford
17 Harris Shore Road Gilford NH
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Feb 10 to Feb 11
CA $184
CA $199 total
Feb 10 - Feb 11
includes taxes & fees
8.8/10 Excellent! (937 reviews)
We were so impressed with the room. The service was excellent and all the staff friendly and helpful. The pool and hot tub were wonderful to enjoy. The hotel was sooo clean. The breakfast in the morning was an added bonus. Would definitely stay here again.
Reviewed on Feb 3, 2026

Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Mar 1 to Mar 2
CA $144
CA $156 total
Mar 1 - Mar 2
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Great room. Very clean and newer looking. Family loved the breakfast the next day.
Reviewed on Feb 1, 2026

Homewood Suites by Hilton Dover
21 Members Way Dover NH
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Feb 15 to Feb 16
CA $152
CA $165 total
Feb 15 - Feb 16
includes taxes & fees
9/10 Wonderful! (762 reviews)
Staff were very friendly and helpful. Rooms were spacious, beds we’re super comfortable.
Reviewed on Feb 7, 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.
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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.







