Ashland Vacation Packages
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Your Ashland Vacation
Take the stress out of planning your next amazing adventure with a Ashland vacation package. Whether you're interested in its history, food or something else, this city offers countless exciting experiences to delve into. If your trip to Ashland includes a little sightseeing, visit popular attractions like Framingham State University, Shoppers World and Natick Collection. That dream Ashland vacation is a couple of clicks away. Search hotels, airfares and more on Expedia for a trip that's tailored to suit your style.
Top Ashland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Atlas Hotel
Allston
Price was CA $1,491, price is now CA $1,012 per person
CA $1,012
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (150 reviews)
New and well presented hotel in a great location to access Cambridge and Boston
Reviewed on Jun 23, 2026
Boston Harbor Hotel
North End
Price was CA $5,318, price is now CA $2,797 per person
CA $2,797
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) 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
Eurostars The Boxer
West End
Price was CA $3,715, price is now CA $2,587 per person
CA $2,587
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.8/10 Excellent! (1,524 reviews)
Very nice hotel. Clean, functional and a great place for a romantic trip. Would absolutely stay there again.
Reviewed on Jun 19, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,832, price is now CA $1,294 per person
CA $1,294
per person
Aug 21 - Aug 25
found 13 hours ago
Roundtrip non-stop 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
Ashland Hotel Deals
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 19 to Jul 20
CA $215
CA $292 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (2,384 reviews)
"My Favorite Boston Hotel. Affordability w 5 star services. Balcony rooms are my go to : )"
Reviewed on Jun 24, 2026
The Midtown Hotel MOD Collection by Sonesta
220 Huntington Avenue Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Jun 30 to Jul 1
CA $255
CA $297 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very good! (501 reviews)
"The hotel was fine, really quiet which was nice. Not far from the T so we didn't need to use our car. It's a little dated, but otherwise it did the job."
Reviewed on Jun 24, 2026
citizenM Boston Back Bay
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Jul 1 to Jul 2
CA $216
CA $252 total
Jul 1 - Jul 2
includes taxes & fees
9.4/10 Exceptional! (2,792 reviews)
"Great location and able to walk everywhere."
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.
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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.
