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.
The Boston Hotel
Brighton
Price was CA $714, price is now CA $549 per person
CA $549
per person
Mar 14 - Mar 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (802 reviews)
Everyone was nice, the room was decent size and there were options. Water was HOT! I loved it
Reviewed on Feb 3, 2026
Boston Harbor Hotel
North End
Price was CA $2,201, price is now CA $1,490 per person
CA $1,490
per person
Apr 3 - Apr 6
found 21 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 Charles Hotel
West Cambridge
Price was CA $2,104, price is now CA $1,566 per person
CA $1,566
per person
Mar 12 - Mar 16
found 20 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out
Reviewed on Jan 25, 2026
Raffles Boston
Back Bay
Price was CA $3,163, price is now CA $2,384 per person
CA $2,384
per person
Apr 23 - Apr 26
found 24 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Everything was great — room was immaculate, hotel was very nice. Would return!
Reviewed on Feb 1, 2026
The Langham, Boston
Downtown Boston
Price was CA $1,572, price is now CA $1,194 per person
CA $1,194
per person
Apr 3 - Apr 6
found 21 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
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 22 to Feb 23
CA $231
CA $258 total
Feb 22 - Feb 23
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 Mar 3 to Mar 4
CA $196
CA $219 total
Mar 3 - Mar 4
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
.
Reviewed on Jan 27, 2026
DoubleTree by Hilton Hotel Boston - Westborough
5400 Computer Dr Westborough MA
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Mar 1 to Mar 2
CA $145
CA $162 total
Mar 1 - Mar 2
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
We checked in late and were really hungry. We just missed the kitchen at the hotel bar. Mark was super friendly and helpful. He gave us some warm yummy cookies and gave a great recommendation for a pub down the road that had a kitchen that was open late. The room was very clean and updated. We slept ...
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.
