Sterling Vacations from $550

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.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $894, price is now $550 per person
$550
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,590, price is now $1,516 per person
$1,516
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $2,101, price is now $1,266 per person
$1,266
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
had a delicious muffin and coffee. Parking was safe and convenient.

Reviewed on Jun 22, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,228, price is now $755 per person
$755
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,015 reviews)
Expensive 2 star hotel. Stayed here twice and 2 star is the highest I could rate it. Not value for money. Trying to be something it is not and hiking the prices up for the World Cup is shameful. Tired dated and an average hotel

Reviewed on Jun 23, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was $1,277, price is now $835 per person
$835
per person
Jul 30 - Aug 2
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (457 reviews)
I love the design of the hotel! The pods are really spacious and provide a lot of privacy. This is my second stay here and will always return when I’m back in Boston!

Reviewed on Jun 21, 2026

Don't see what you're looking for?
See all available trips from Columbus to Sterling
View all trips

Stay near popular Sterling attractions

Davis' Farmland & Mega Maze

7.0/5 (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 Jun 28 to Jun 29
$178 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (166 reviews)
"It’s a lovely inn and very quiet. Nice bathroom, but when we were there the room maintenance seems to have fallen behind - but that may not be the case in the rest of the inn."

Reviewed on Jun 24, 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
$146 nightly
The price is $163 total per night from Jul 5 to Jul 6
$163 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (1,013 reviews)
"Fun place for kids"

Reviewed on Jun 24, 2026

Great Wolf Lodge Boston / Fitchburg, MA
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
5400 Computer Dr Westborough MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $146 total per night from Jul 20 to Jul 21
$146 total
Jul 20 - Jul 21
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"The mattress was old or cheap because it felt indented when I woke up the next morning and caused my back to hurt. The AC unit in the room also kept making a loud noise every few minutes- like clockwork, so I kept having to turn it off after a few minutes. Especially at night so I could sleep. I ..."

Reviewed on Jun 22, 2026

DoubleTree by Hilton Hotel Boston - Westborough
See all 410 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Sterling vacation package cost?
You'll find cheap prices from $550 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.