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.
The Godfrey Hotel Boston
Downtown Boston
CA $1,834
per person
Sep 30 - Oct 5
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (5,158 reviews)
Hotel was perfect location for my first real trip in Boston. Everything seemed at a walkable distance whether it’s food options, parks, subway access, or just fun city activities. Staff was amazing! Appreciate all the little details of individual toiletries, robes/slippers, and adequate amount of outlets. Would definitely recommend this hotel!
Reviewed on Aug 7, 2026
Sesuit Harbor House
CA $987
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (196 reviews)
The Sesuit Harbor House is awesome. Has a very Cape Cod feel, the owners are excellent very attentive and have done an awesome job with this property. There is a beautiful fire pit, pool, nice outside areas to eat and relax and they also have goats! I highly recommend, close to dining and beaches as well.
Reviewed on Aug 1, 2026
The Mansion at Ocean Edge
CA $2,979
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (1,004 reviews)
The amenities are nice, and the beach is beautiful. We had a Deluxe Double Queen room on the 1st floor of the East wing which was a nice size and had a spacious bathroom. The main disappointment with the room was that it faced the back with no view whatsoever. The beach and pool got very crowded by early afternoon. Although the mansion and grounds were beautiful, I wouldn't really consider this to be a "luxury" hotel.
Reviewed on Aug 8, 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 $222
CA $248 total
Aug 23 - Aug 24
includes taxes & fees
Great Wolf Lodge Boston / Fitchburg, MA
150 Great Wolf Dr Fitchburg MA
CA $208
CA $232 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
"Our family had a blast. So many activities for the kids. The staff is so generous with their time and attentive to the guest needs. My son wants to go back next year."
Reviewed on Aug 7, 2026
La Quinta Inn by Wyndham Auburn Worcester
446 Southbridge St Auburn MA
Fully refundableReserve now, pay when you stay
CA $110
CA $123 total
Aug 16 - Aug 17
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.
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 $700 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.
