Sterling Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Encore Boston Harbor
CA $1,099
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (4,227 reviews)
It’s always a lovely stay at the encore but the rooms are showing wear and our shades didn’t shut. They came and got them shut but we couldn’t open them in the am. Ready for a facelift, but always a good time.
Reviewed on Oct 10, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,664
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
Ready to book your vacation to Sterling?
Sterling Hotel Deals
Chocksett Inn and Restaurant
59 Laurelwood Road Sterling MA
Fully refundableReserve now, pay when you stay
CA $227
CA $253 total
Oct 11 - Oct 12
includes taxes & fees
8.8/10 Excellent! (192 reviews)
"Good for one night stopover."
Reviewed on Oct 4, 2026
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd Framingham MA
Fully refundableReserve now, pay when you stay
CA $147
CA $167 total
Oct 26 - Oct 27
includes taxes & fees
Extended Stay America Suites Boston Westborough Computer Dr
1800 Computer Dr Westborough MA
Fully refundableReserve now, pay when you stay
CA $125
CA $139 total
Nov 7 - Nov 8
includes taxes & fees
6.8/10 (1,007 reviews)
"It was okay rooms were clean and awesome"
Reviewed on Oct 10, 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.
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.
Mary Had a Little Lamb Statue
You can find out about the history of Sterling when you stop by Mary Had a Little Lamb Statue. Experience the area's festivals and entertainment venues.
Frequently asked questions
How much does a Sterling vacation package cost?
You can grab a vacation package to this popular destination from CA $1,099 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?
- 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.
- 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.
- 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.
- 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.
