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.
Boston Harbor Hotel
North End
CA $1,229
per person
Dec 4 - Dec 7
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great hotel at a terrific site. The North End restaurants and Faneuil Hall are both at walkable distances. Everywhere we were in the Hotel there was always a staff member asking if we needed help. We loved out stay at the Boston Harbor Hotel.
Reviewed on Sep 22, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Lexington Green Historic District
CA $1,576
per person
Oct 22 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9.6/10 Exceptional! (265 reviews)
I had a King room with a fireplace, it was a nice size room and very clean. The bathroom was nice and they had a robe hanging for me. Little touches like personalized notes and soft drinks in the refrigerator and snacks to pick up for the room. The staff was very friendly. I'm not a breakfast eater so can't really comment on that although there was a nice continental spread and you could order off the menu. I will say that I was a bit disappointed in the restaurant. Had dinner there the night before and for the price, I felt the food was a little lackluster. The bartender was very nice and he was my server as well. All in all I really enjoyed my stay and if I go back to Lexington I would stay there again.
Reviewed on Sep 4, 2026
Furnished Apartment Near Longwood
North Brookline
CA $1,273
per person
Oct 22 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
7/10 Good! (6 reviews)
Super cute apartment! Stayed the weekend to visit out soon at college. Locations was close to everything beds were super comfortable, would stay here again.
Reviewed on Sep 13, 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 $223
CA $249 total
Sep 27 - Sep 28
includes taxes & fees
Extended Stay America Suites Boston Westborough Computer Dr
1800 Computer Dr Westborough MA
Fully refundableReserve now, pay when you stay
CA $127
CA $141 total
Sep 29 - Sep 30
includes taxes & fees
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd Framingham MA
Fully refundableReserve now, pay when you stay
CA $119
CA $135 total
Sep 23 - Sep 24
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 $1,209 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.
