Milton Vacation Packages
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Your Milton Vacation
Book a Milton vacation package and get set to experience all this lively city has to offer. Consider staying in the neighborhood of Downtown Boston, which is good for nightlife, shopping and bars and pubs. South Shore Plaza, Blue Hills Ski Area and F1 Boston are just a few of the sights worth visiting during your trip to Milton. No matter your travel plans or the size of your budget, organizing a tailored Milton vacation is a breeze with Expedia.
Top Milton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,379, price is now CA $901 per person
CA $901
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (189 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year
Reviewed on Jun 18, 2026
Boston Harbor Hotel
North End
Price was CA $3,154, price is now CA $1,883 per person
CA $1,883
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on Jun 15, 2026
Chatham Tides
Price was CA $2,645, price is now CA $1,753 per person
CA $1,753
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (713 reviews)
Property is located on the beach, and that’s a huge plus. Rooms are clean, and the staff was pleasant to deal with. I met fellow travelers that book the same room on the same weeks for many years in a row, and that should tell you something.
Reviewed on Jun 23, 2026
Ashworth by the Sea
Hampton Beach
Price was CA $2,482, price is now CA $1,775 per person
CA $1,775
per person
Jul 26 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (1,345 reviews)
Access and location to beach was great and staff was helpful. Elevator did not work, fridge in room would not get cold, water never turned hot and had to ask for refill for shampoo and conditioner.
Reviewed on Jun 25, 2026
The Langham, Boston
Downtown Boston
Price was CA $2,204, price is now CA $1,603 per person
CA $1,603
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,015 reviews)
Expensive 2 star hotel. Stayed here twice and 2 star is the highest I could rate it. Not value for money. Trying to be something it is not and hiking the prices up for the World Cup is shameful. Tired dated and an average hotel
Reviewed on Jun 23, 2026
Milton Hotel Deals
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Jun 30 to Jul 1
CA $204
CA $237 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (2,698 reviews)
"Clean room, friendly staff and a perfect location! There’s a 711 right across the street! 10/10!"
Reviewed on Jun 25, 2026
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jul 2 to Jul 3
CA $215
CA $292 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (2,385 reviews)
"The front desk charged me for two night of overparking when I had a car only for one overnight parking. In addition, as I left the parking lot the machine charged me additional $18.00. The night I reported the one night overnight parking in the front desk, waited for about 25 minutes since frontdesk ..."
Reviewed on Jun 25, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Jul 26 to Jul 27
CA $228
CA $314 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,475 reviews)
"3rd time in Boston, 3rd time staying here! It’s the only hotel in Boston I will book."
Reviewed on Jun 25, 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 Milton attractions
What to do in Milton
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $73
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
88% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $116
per adult
92% of travellers recommend
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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.
