Sterling Vacation Packages

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    Save up to CA $4,200 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.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,643, price is now CA $1,156 per person
CA $1,156
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
The property was beautiful and super clean. Breakfast was really good. The staff was very polite and helpful! I’d love to come back again!

Reviewed on Nov 6, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,564, price is now CA $1,227 per person
CA $1,227
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,202, price is now CA $1,248 per person
CA $1,248
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,406, price is now CA $1,579 per person
CA $1,579
per person
Jan 29 - Feb 1
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,383, price is now CA $1,635 per person
CA $1,635
per person
Jan 29 - Feb 1
just found
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

Ready to book your vacation to Sterling?

 

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Sterling Hotel Deals

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road Sterling MA
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Dec 7 to Dec 8
CA $222
CA $248 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (194 reviews)
"This is a very quaint property. A lot of charm but most important very clean with ample size rooms. We have stayed there before and will again."

Reviewed on Oct 25, 2026

Chocksett Inn and Restaurant
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd Framingham MA
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Nov 16 to Nov 17
CA $130
CA $148 total
Nov 16 - Nov 17
includes taxes & fees
Motel 6 Framingham, MA - Boston West
Monticello Inn Framingham

Monticello Inn Framingham

2.5 out of 5
90 Worcester Rd Framingham MA
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Nov 9 to Nov 10
CA $114
CA $127 total
Nov 9 - Nov 10
includes taxes & fees
4.8/10 (1,002 reviews)
"The photos do not match the state of the property. The rooms are filthy and unkempt. If they were clean I could deal with being outdated or things like the comforter not even fitting the bed. Even the front lobby doesn’t match the photos."

Reviewed on Nov 5, 2026

Monticello Inn Framingham
See all 432 properties in Sterling
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Sterling attractions

Davis' Farmland & Mega Maze

7.0/10 (2 reviews)
Enjoy an outing to Davis' Farmland & Mega Maze during your stay in Sterling. You can attend a sporting event while in the area.
See properties

Frequently asked questions

How much does a Sterling vacation package cost?
You can grab a vacation package to this popular destination from CA $1,156 on Expedia. But how much your vacation to Sterling costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Sterling?
The off-season is the best time to visit Sterling if you're hoping to keep costs down. Another tip for finding cheap Sterling vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Sterling?
Usually, a handful of days is enough to go to the major attractions during your Sterling vacation. However, if you prefer to have some time to chill out or take day tours, think about extending your trip.
How to find the best Sterling package deals?
Bagging a cheap Sterling package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Sterling package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Sterling vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can personalize your Sterling getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Sterling?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Sterling getaway.
How to plan a trip to Sterling?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the activities on offer will also help you decide when to vacation in Sterling.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will probably be the biggest expense during your trip to Sterling.
  3. Work out your trip length: Consider how long you'd like to spend discovering Sterling. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Sterling vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.