An aerial view of a town surrounded by dense forests, with a mix of residential and commercial buildings, and a prominent church.

Sterling Vacations from $501

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, 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.

The Latest Sterling Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 15 - Jan 18

    Iris Hotel Cape Cod + Flight

    Falmouth
    3 nights
    3.0 star property
    8.4/10 - Very good (437 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $847
    $501
    per traveler
    found 23 hours ago
    Iris Hotel Cape Cod
  • Dec 21 - Dec 26

    Boston Lodge and Suites + Flight

    Dorchester
    5 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • Nonstop
    $1,565
    $769
    per traveler
    found 13 hours ago
    Boston Lodge and Suites
  • Jan 25 - Jan 29

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $1,994
    $1,147
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Jan 15 - Jan 18

    Sea Crest Beach Resort + Flight

    North Falmouth
    3 nights
    3.5 star property
    7.6/10 - Good (550 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $710
    $503
    per traveler
    found 23 hours ago
    Sea Crest Beach Resort
  • Jan 15 - Jan 18

    Brewster Green Resort + Flight

    Brewster
    3 nights
    3.5 star property
    9.4/10 - Exceptional (153 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $757
    $540
    per traveler
    found 23 hours ago
    Brewster Green Resort

Where to stay near Sterling

Sterling, Massachusetts, offers a perfect weekend getaway with its blend of adventure and relaxation. Explore the heart of Sterling and the charming area around Sterling, including downtown Westminster. Enjoy skiing opportunities and family-friendly activities, making it an ideal destination for all types of travelers.

Worcester

For travelers seeking a vibrant experience, Worcester offers a rich blend of entertainment and culture just about 12 miles drive from Sterling. With attractions like the DCU Center for arena events, the historic College of the Holy Cross, and the Worcester Art Museum, there’s something to engage every visitor. Plus, the city is easily accessible, making it an ideal base for exploring the region. Choosing Worcester for your stay ensures a memorable getaway filled with diverse activities and experiences.

Fitchburg

Experience the charm of Fitchburg, an excellent hub for travelers eager to enjoy outdoor adventures and entertainment. This vibrant city is just 10 miles from Sterling and offers attractions like the Great Wolf Lodge Waterpark for family fun, the historic Fitchburg State University for a cultural touch, and Game On Fitchburg for sports enthusiasts. With a steady flow of visitors year-round, Fitchburg is a smart choice for your stay, providing diverse experiences right at your doorstep.

Leominster

Make your vacation planning effortless by staying in Leominster, a haven for families and outdoor enthusiasts due to its proximity to exciting attractions. Explore the thrills of Great Wolf Lodge Waterpark, enjoy a day at the family beach, or visit the historic Fitchburg State University. With a variety of sports and adventure activities available, Leominster offers something for everyone. Located about 6 miles from Sterling, this city is a smart choice for travelers seeking a memorable experience.

Marlborough

Ideally situated for families and weekend getaway enthusiasts, Marlborough offers a vibrant mix of entertainment and outdoor experiences. Visitors can explore the scenic Tower Hill Botanic Garden, enjoy a round of golf at the Marlborough Country Club, or unwind at Hopkinton State Park. With its attractions peaking in March to April and July, Marlborough is an excellent choice year-round. Located about 14 miles by car from Sterling, it’s a smart destination for travelers looking to recharge and explore.

Clinton

Travelers visiting the area often choose Clinton as a charming base for their vacation, especially families and outdoor enthusiasts seeking adventure and scenic beauty. With attractions like the Tower Hill Botanic Garden and the Great Wolf Lodge Waterpark, there's something for everyone. Just 4 miles from Sterling, Clinton offers easy access to local lakes and beaches, making it perfect for weekend getaways. Clinton is a smart choice for your stay, blending relaxation with adventure.

Discover the most popular places to visit in Sterling

Sterling Hotel Deals

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.

Frequently Asked Questions

How much does a Sterling vacation package cost?

You'll find cheap prices from $501 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.