Sterling Vacations from $637
Book a Hotel + Flight or Car together to unlock savings
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.
Battery Wharf Hotel, Boston Waterfront
North End
$637
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,041 reviews)
This spot used to be lovely. The hotel needs a major makeover. When I got into my room, all of the drawers, including the dresser and desk were open. It was very odd.
The property is just not well maintained. And there’s an awful noise that keeps you up all night from these weird generator things. Overall, the amount of money you spend here is completely not worth it.
The bartender is lovely and the bar is fine but there’s really nothing special that they offer and there’s just so much that they could do to make this place great again.
Reviewed on Oct 15, 2026
Four Seasons Hotel Boston
Bay Village
$1,241
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Raffles Boston
Back Bay
$1,845
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (332 reviews)
A stunning hotel with super helpful staff. Would highly recommend the Raffles, from start to finish it was excellent and we’ll definitely be back.
Reviewed on Oct 14, 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
Oct 18 - Oct 19
Total with taxes and fees
8.8/10 Excellent! (192 reviews)
"Good for one night stopover."
Reviewed on Oct 4, 2026
The Verve Hotel Boston Natick, Tapestry Collection by Hilton
1360 Worcester St Natick MA
Fully refundableReserve now, pay when you stay
$114 nightly
$127 total
Nov 14 - Nov 15
Total with taxes and fees
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd Framingham MA
Fully refundableReserve now, pay when you stay
$96 nightly
$107 total
Nov 15 - Nov 16
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 $637 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.
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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.