Sterling Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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 $2,850, price is now CA $1,722 per person
CA $1,722
per person
Oct 23 - Oct 26
found 17 hours 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
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 10 hours 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
Fully refundableReserve now, pay when you stay
The price is CA $262 per night from Sep 11 to Sep 12
CA $262
CA $292 total
Sep 11 - Sep 12
includes taxes & fees
Courtyard by Marriott Boston Marlborough
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Sep 21 to Sep 22
CA $159
CA $178 total
Sep 21 - Sep 22
includes taxes & fees
Courtyard by Marriott Boston Natick
342 Speen St, Natick, MA
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Sep 21 to Sep 22
CA $165
CA $184 total
Sep 21 - Sep 22
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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
