Sterling Vacations from $495
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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.
The Latest Sterling vacation packages
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
$495
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
The Mansion at Ocean Edge
$847
per person
Nov 11 - Nov 14
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.2/10 Very Good! (1,002 reviews)
Kyung and his team delivered on a special weekend get away for my wife’s 40th birthday! This is now our next favorite place on the cape and we look forward to many more memories being made @ Ocean Edge!
Thank you all!
The Contino’s
Reviewed on Sep 6, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
$867
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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
Stay near popular Sterling attractions
Davis' Farmland & Mega Maze
7.0/10 (2 reviews)
Davis Farmland offers hands-on encounters with rare endangered farm animals in a family-friendly setting. Explore the seasonal Mega Maze or cool off at the interactive water spray park during summer.
Mary Had a Little Lamb Statue
This life-sized bronze lamb commemorates the origins of the famous "Mary Had a Little Lamb" nursery rhyme. Read the accompanying plaques to discover the true story of Mary Sawyer and her pet lamb.
Sterling Hotel Deals
Chocksett Inn and Restaurant
59 Laurelwood Road Sterling MA
Fully refundableReserve now, pay when you stay
$159 nightly
$178 total
Sep 13 - Sep 14
Total with taxes and fees
8.6/10 Excellent! (186 reviews)
"Staff were very friendly and helpful. Room was clean, quiet, and quaint. Very nice place to stay."
Reviewed on Sep 5, 2026
Great Wolf Lodge Boston / Fitchburg, MA
150 Great Wolf Dr Fitchburg MA
$184 nightly
$205 total
Sep 22 - Sep 23
Total with taxes and fees
Courtyard by Marriott Boston Marlborough
75 Felton St Marlborough MA
Fully refundableReserve now, pay when you stay
$135 nightly
$151 total
Sep 17 - Sep 18
Total with taxes and 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.
Find the Best Sterling Vacation Packages
Sterling Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Worcester Regional Airport (ORH) |
Population | 7,400 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Apex Entertainment Center, Wachusett Mountain Ski Area and Worcester Art Museum |
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Frequently asked questions
How much does a Sterling vacation package cost?
You'll find cheap prices from $495 on Expedia for your Sterling escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Sterling costs.
What are the cheapest months to go to Sterling?
If you're hoping to score a cheap Sterling vacation package, consider visiting in May, November and December. You'll generally find lower prices on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Sterling?
With a well-organized schedule, you can easily visit the top Sterling sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, think about booking your Sterling vacation for longer.
How to find the best Sterling package deals?
Use Expedia's handy filters to help you find some of the best Sterling package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Sterling package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Sterling vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a tailored Sterling vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Sterling?
Land incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Sterling vacation.
Does Expedia offer Book Now, Pay Later Sterling vacation packages?
Secure your dream getaway to Sterling with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for the next payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up cheap deals before they disappear.
Explore a world of travel with Expedia
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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.
