Sterling Vacation Packages
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Better together
Save up to CA $1,096 when you book a flight and hotel together*
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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.
Raffles Boston
Back Bay
Price was CA $2,361, price is now CA $1,331 per person
CA $1,331
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (159 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.
Reviewed on Sep 2, 2025
The Langham, Boston
Downtown Boston
Price was CA $2,075, price is now CA $1,332 per person
CA $1,332
per person
Nov 9 - Nov 12
found 23 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,011 reviews)
First rate hotel. Definitely a Luxury hotel stay!
Reviewed on Sep 1, 2025
DoubleTree Suites by Hilton Hotel Boston - Cambridge
Allston
Price was CA $1,302, price is now CA $866 per person
CA $866
per person
Nov 4 - Nov 8
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.8/10 Excellent! (1,015 reviews)
Delicious breakfast! Clean, spacious room and friendly staff.
Reviewed on Sep 9, 2025
Sterling Hotel Deals
Chocksett Inn and Restaurant
59 Laurelwood Road, Sterling, MA
The price is CA $261 per night from Sep 10 to Sep 11
CA $261
CA $291 total
Sep 10 - Sep 11
includes taxes & fees
Courtyard by Marriott Boston Marlborough
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 14 to Sep 15
CA $186
CA $208 total
Sep 14 - Sep 15
includes taxes & fees
Courtyard by Marriott Boston Natick
342 Speen St, Natick, MA
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Sep 14 to Sep 15
CA $153
CA $171 total
Sep 14 - Sep 15
includes taxes & fees
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.
