Sterling Vacations from $469

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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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $988, price is now $469 per person
$469
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was $1,970, price is now $1,059 per person
$1,059
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.

Reviewed on Oct 13, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,215, price is now $747 per person
$747
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,086 reviews)
Great service from reception staff, and bustling cosy restaurant.

Reviewed on Oct 13, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,304, price is now $808 per person
$808
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
This is a lovely hotel with great facilities in a superb location.

Reviewed on Oct 21, 2025

AC Hotel by Marriott Boston Downtown

AC Hotel by Marriott Boston Downtown

3.5 out of 5
South End
Save 100% on your flight
Price was $824, price is now $574 per person
$574
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,008 reviews)
good location to walk around and explore.

Reviewed on Oct 21, 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 Oct 26 to Oct 27
$178 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (136 reviews)
Staff was wonderful. Would highly recommend this hotel.

Reviewed on Sep 29, 2025

Chocksett Inn and Restaurant
Inn at Historic Concord

Inn at Historic Concord

3 out of 5
740 Elm St, Concord, MA
8.2/10 Very Good! (1,006 reviews)
Clean room

Reviewed on Oct 22, 2025

Get rates
Inn at Historic Concord
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
$114 nightly
The price is $127 total per night from Nov 24 to Nov 25
$127 total
Nov 24 - Nov 25
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Very clean nice hotel!

Reviewed on Oct 23, 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 359 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 $469 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.