Sterling Vacation Packages
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Your Sterling Vacation
Our Sterling vacation packages offer countless opportunities to discover new sights, sounds and sensations. And with all the planning taken care of, you can relax and enjoy your city break in the way that you deserve. Tower Hill Botanic Garden, Museum of Russian Icons and Dexter Drumlin are just a few of the sights worth exploring during your trip to Sterling. Expedia is here to help you escape the everyday. Tailor your vacation to Sterling to suit your style of travel, whatever that may be.
Top Sterling Vacation Deals
Price found within the past 48 hours. Click for updated prices.
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 13 hours 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 19 hours 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
DoubleTree Suites by Hilton Hotel Boston - Cambridge
Allston
Price was CA $1,302, price is now CA $887 per person
CA $887
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,000 reviews)
Staff was great we were treated with warm chocolate chip cookies. but Expedia told us breakfast was included and that was a lie
Reviewed on Feb 2, 2026
Sterling Hotel Deals
Chocksett Inn and Restaurant
59 Laurelwood Road Sterling MA
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Feb 9 to Feb 10
CA $231
CA $258 total
Feb 9 - Feb 10
includes taxes & fees
8.6/10 Excellent! (150 reviews)
Updated rooms, clean throughout. Staff were welcoming.
Reviewed on Feb 1, 2026
Great Wolf Lodge Boston / Fitchburg, MA
150 Great Wolf Dr Fitchburg MA
The price is CA $196 per night from Feb 11 to Feb 12
CA $196
CA $219 total
Feb 11 - Feb 12
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Good
Reviewed on Feb 7, 2026
The Colonial Hotel
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,001 reviews)
Friendly staff, clean room, gym and poll area.
Reviewed on Feb 4, 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.
