
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.

Lakeside Inn
Price was CA $1,094, price is now CA $703 per person
CA $703
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,162 reviews)
We stayed for one night. When we arrived the restaurant was just jumping with excitement with families and others singing karaoke. It was a nice welcome. We checked out the pool. It was a little cold but the kids had a quick dip and were happy. The staff was amazing. Such great customer service. From the staff that checked us in, the gentleman that cooked breakfast and the lady that cleaned the rooms. The maintenance man helped us with a little issue faster than my toddler could asking him a million questions which is lightning speed. Checkout was also great! 10/10 would definitely stay here again. Rooms were comfortable, quiet, and clean! Great water pressure for the kids baths and showers.
Reviewed on Aug. 28, 2025


Raffles Boston
Back Bay
Price was CA $2,781, price is now CA $1,651 per person
CA $1,651
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.
Reviewed on Aug. 28, 2025


Sesuit Harbor House
Price was CA $1,406, price is now CA $911 per person
CA $911
per person
Oct 23 - Oct 27
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (168 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!
Reviewed on Aug. 25, 2025
Sterling Hotel Deals

Chocksett Inn and Restaurant
59 Laurelwood Road, Sterling, MA
Fully refundableReserve now, pay when you stay
The price is CA $260 per night from Aug 31 to Sep 1
CA $260
CA $290 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (134 reviews)
Short Stay
"Everything went smoothly, but for the noisy air conditioning system and the very noisy toilet!!! Other than that nice, clean, no disturbances at all."
Reviewed on Jun. 25, 2025

Courtyard by Marriott Boston Natick
342 Speen St, Natick, MA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Sep 4 to Sep 5
CA $142
CA $159 total
Sep 4 - Sep 5
includes taxes & fees

Courtyard by Marriott Boston Marlborough
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Sep 4 to Sep 5
CA $162
CA $181 total
Sep 4 - Sep 5
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.