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.
Maverick Suites at 245 Newbury St
Back Bay
Price was CA $1,511, price is now CA $1,069 per person
CA $1,069
per person
Mar 18 - Mar 24
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (151 reviews)
Room was clean and a good size. Location was perfect - walking distance to where I needed to be.
Reviewed on Dec 2, 2025
Boston Harbor Hotel
North End
Price was CA $2,201, price is now CA $1,490 per person
CA $1,490
per person
Apr 3 - Apr 6
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 Charles Hotel
West Cambridge
Price was CA $2,104, price is now CA $1,566 per person
CA $1,566
per person
Mar 12 - Mar 16
found 24 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out
Reviewed on Jan 25, 2026
Raffles Boston
Back Bay
Price was CA $3,163, price is now CA $2,384 per person
CA $2,384
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Everything was great — room was immaculate, hotel was very nice. Would return!
Reviewed on Feb 1, 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 $179 per night from Feb 9 to Feb 10
CA $179
CA $195 total
Feb 9 - Feb 10
includes taxes & fees
8.8/10 Excellent! (932 reviews)
Great everything
Reviewed on Jan 24, 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Mar 1 to Mar 2
CA $145
CA $157 total
Mar 1 - Mar 2
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Room was clean and staff was great.
Reviewed on Jan 30, 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 19 to Feb 20
CA $152
CA $165 total
Feb 19 - Feb 20
includes taxes & fees
9/10 Wonderful! (760 reviews)
easy check in/check out. Clean room, beds comfy
Reviewed on Jan 23, 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.
