Sterling Vacations from $696

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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.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $984, price is now $696 per person
$696
per person
Apr 5 - Apr 10
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (4,672 reviews)
Friendly staff, clean room, good location.

Reviewed on Jan 27, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,341, price is now $884 per person
$884
per person
Apr 5 - Apr 10
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
The staff was fantastic!

Reviewed on Jan 24, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $2,458, price is now $1,672 per person
$1,672
per person
Apr 16 - Apr 22
found 18 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,206, price is now $825 per person
$825
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
beautiful, clean rooms, well appointed

Reviewed on Jan 23, 2026

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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
$169 nightly
The price is $189 total per night from Jan 29 to Jan 30
$189 total
Jan 29 - Jan 30
Total with taxes and fees
8.6/10 Excellent! (148 reviews)
The staff was very accommodating and friendly. Quaint place to stay.

Reviewed on Jan 16, 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
$179 nightly
The price is $200 total per night from Feb 1 to Feb 2
$200 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
Great staff

Reviewed on Jan 24, 2026

Great Wolf Lodge Boston / Fitchburg, MA
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd Framingham MA
Fully refundable
$71 nightly
The price is $75 total per night from Jan 29 to Jan 30
$75 total
Jan 29 - Jan 30
Total with taxes and fees
6.8/10 (1,130 reviews)
Room was clean

Reviewed on Jan 17, 2026

Motel 6 Framingham, MA - Boston West
See all 392 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 $696 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.