Sterling Vacations from $739

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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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,096, price is now $739 per person
$739
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,524 reviews)
Eurostars has an ideal location for those that want to explore downtown Boston! The hotel was extremely clean and secure. Highly recommend!!

Reviewed on Jul 13, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,659, price is now $1,472 per person
$1,472
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Great location and very helpful staff

Reviewed on Jul 16, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $2,339, price is now $1,310 per person
$1,310
per person
Sep 3 - Sep 10
found 8 hours ago
Roundtrip flight included
Chicago (CHI) 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

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,495, price is now $1,471 per person
$1,471
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,249, price is now $1,460 per person
$1,460
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)

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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.
See properties

Sterling Hotel Deals

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road Sterling MA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $178 total per night from Jul 19 to Jul 20
$178 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (171 reviews)
"Spacious room and bathroom. Staff very friendly and helpful."

Reviewed on Jul 12, 2026

Chocksett Inn and Restaurant
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$149 nightly
The price is $166 total per night from Jul 20 to Jul 21
$166 total
Jul 20 - Jul 21
Total with taxes and fees
8.6/10 Excellent! (1,029 reviews)
"We had an excellent stay! The staff was friendly, helpful, and always ready to assist. We especially loved the water slides—they were a lot of fun. The only downside for me was that the beds were too firm. However, if you prefer a hard mattress, you’ll probably find them comfortable. Overall, it ..."

Reviewed on Jul 16, 2026

Great Wolf Lodge Boston / Fitchburg, MA
Best Western Royal Plaza Hotel & Trade Center

Best Western Royal Plaza Hotel & Trade Center

3 out of 5
181 Boston Post Rd W Marlborough MA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $128 total per night from Jul 26 to Jul 27
$128 total
Jul 26 - Jul 27
Total with taxes and fees
Best Western Royal Plaza Hotel & Trade Center
See all 414 properties in Sterling
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 $739 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.