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.
Hotel Ivy Boston Common
Bay Village
Price was CA $1,455, price is now CA $968 per person
CA $968
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
I was only here because I had an early flight out of Boston the next morning. I arrived way past standard check in time (3-4 pm), and the staff were very communicative, friendly and understanding. The room did the trick for just an overnight. Comfortable beds with comfortable pillows. Loved the bathroom. Loved the lighting. Only thing to note for future travelers that may be “negative”: The pictures make the room look much bigger than it is, like the size of a standard hotel room. It is about 1/4 of the size of a normal hotel room. At least this was the case for my room.
Reviewed on May 6, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $2,769, price is now CA $1,773 per person
CA $1,773
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!
Reviewed on Sep 20, 2025
Chatham Tides
Price was CA $2,425, price is now CA $1,682 per person
CA $1,682
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (687 reviews)
Very peaceful except the folks upstairs. We were bottom level ocean view. Lovely newly renovated room. Incredible staff. I live 11 hrs away and parents both in nearby wonderful nursing home, LC. Easy drive to see them. Family home gone now but was certainly made to feel at home here.
Reviewed on May 6, 2026
Sterling Hotel Deals
Chocksett Inn and Restaurant
59 Laurelwood Road Sterling MA
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from May 28 to May 29
CA $217
CA $242 total
May 28 - May 29
includes taxes & fees
8.8/10 Excellent! (153 reviews)
The directions for the tv stopped short on how to use the remote once the tv was turned on, We have a different cable provider at home and the remote was different.
Reviewed on May 6, 2026
Great Wolf Lodge Boston / Fitchburg, MA
150 Great Wolf Dr Fitchburg MA
Fully refundableReserve now, pay when you stay
The price is CA $323 per night from May 11 to May 12
CA $323
CA $361 total
May 11 - May 12
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Wonderful excellent experience!!
Reviewed on May 7, 2026
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd Framingham MA
Fully refundable
The price is CA $112 per night from Jun 7 to Jun 8
CA $112
CA $121 total
Jun 7 - Jun 8
includes taxes & fees
7/10 Good! (1,219 reviews)
Room is very clean and comfortable
Reviewed on May 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.
