Milton Vacation Packages
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Your Milton Vacation
Excellent adventures await when you reserve a Milton vacation package. Whether you're a foodie, art buff or just a traveler who appreciates new places, there's something for everyone in this vibrant city. There's lots to see during your trip to Milton, including Sunrise Lake and Marchs Pond. Whoever you're taking time off with and whatever the size of your budget, your dream Milton vacation is just clicks away with Expedia.
Top Milton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Westin Boston Seaport District
Seaport District
Price was CA $1,761, price is now CA $1,172 per person
CA $1,172
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (2,407 reviews)
Wonderful staff, good food options, and great location for the marathon.
Reviewed on Apr 22, 2026
The Highliner Hotel
Downtown Gloucester
Price was CA $4,005, price is now CA $2,701 per person
CA $2,701
per person
Jun 12 - Jun 19
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
10/10 Exceptional! (2 reviews)
Digital check in process was easy to do on my phone. The staff was helpful, it wasnt just automated. The building location was perfect for us to explore the town on foot. Parking was tricky, but they detailed your parking options well. Many food options nearvy. Good night life options even in off season. The building and room were immaculate with a luxery feeling. Music in the hallways, fresh paint, umbrellas by the door, free water station. There was green mountain coffee pods, not the usual hotel mud coffee. 15$ voucher to a nearby cafe was enough for two bagels and two small coffees. Overall, this place was amazing!
Reviewed on Apr 19, 2026
The Mansion at Ocean Edge
Price was CA $4,410, price is now CA $3,018 per person
CA $3,018
per person
Jul 5 - Jul 11
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (1,001 reviews)
Unfortunately, we went during the slow season. They don't open fully until May 1st. The bar wasn't open until 5pm and restaurants were not open. Pool was closed. No chairs on the deck. Everything was covered. Property was nice. Just would have been nice to have a few options.
Reviewed on Apr 24, 2026
Milton Hotel Deals
Luxury Lakehouse with Large Private Beach, Hottub, Tiki Bar, 100’ Covered Deck, and Dock
Milton NH
Garrison Hotel & Suites Dover-Portsmouth, an Ascend Collection Hotel
200 Sterling Way Dover NH
Fully refundable
The price is CA $161 per night from Apr 28 to Apr 29
CA $161
CA $175 total
Apr 28 - Apr 29
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Room was clean. Staff was friendly
Reviewed on Apr 16, 2026
Homewood Suites by Hilton Dover
21 Members Way Dover NH
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Apr 30 to May 1
CA $200
CA $217 total
Apr 30 - May 1
includes taxes & fees
9/10 Wonderful! (793 reviews)
Amazing breakfast! Professional & attentive staff. Comfortable & clean rooms.
Reviewed on Apr 21, 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.
