Sterling Vacations from $338

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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.
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
West End
Price was $479, price is now $338 per person
$338
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
18.4/10 Exceptional! (4,018 reviews)
Clean, great staff, perfect location!

Reviewed on Nov 16, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,137, price is now $446 per person
$446
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,218, price is now $782 per person
$782
per person
Jan 22 - Jan 26
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (1,021 reviews)
Room was clean and tidy

Reviewed on Nov 10, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,352, price is now $916 per person
$916
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
19.6/10 Exceptional! (1,008 reviews)
Rooms were spotless, service was outstanding

Reviewed on Nov 13, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $921, price is now $649 per person
$649
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
19.2/10 Exceptional! (482 reviews)
Staff went above and beyond!

Reviewed on Nov 9, 2025

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Discover the most popular places to visit in Sterling

Davis' Farmland & Mega Maze

Enjoy an outing to Davis' Farmland & Mega Maze during your stay in Sterling. You can attend a sporting event while in the area.

Davis' Farmland & Mega Maze

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 Nov 17 to Nov 18
$178 total
Nov 17 - Nov 18
Total with taxes and fees
8.6/10 Excellent! (140 reviews)
Clean and comfortable

Reviewed on Oct 28, 2025

Chocksett Inn and Restaurant
The Verve Hotel Boston Natick, Tapestry Collection by Hilton

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

3.5 out of 5
1360 Worcester St Natick MA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Nov 23 to Nov 24
$118 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Very nice and clean room.

Reviewed on Nov 14, 2025

The Verve Hotel Boston Natick, Tapestry Collection by Hilton
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $161 total per night from Nov 19 to Nov 20
$161 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Very nice hotel.

Reviewed on Nov 13, 2025

The Colonial Hotel
See all 365 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 $338 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

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