Sterling Vacations from $180

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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.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
Price was $282, price is now $180 per person
$180
per person
Oct 23 - Oct 26
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
7.6/10 Good! (456 reviews)
Everything was great

Reviewed on Aug 18, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $650, price is now $329 per person
$329
per person
Nov 1 - Nov 3
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $698, price is now $430 per person
$430
per person
Oct 26 - Oct 30
found 18 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.2/10 Very Good! (1,007 reviews)
Beautiful area, easy to walk around and sightsee. Room was spacious but has a chlorine smell, average for cleanliness. Dirt, grime around shower doors.

Reviewed on Aug 22, 2025

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $514, price is now $317 per person
$317
per person
Oct 5 - Oct 8
found 22 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,226 reviews)
Consistently excellent stay

Reviewed on Aug 22, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Save 100% on your flight
Price was $387, price is now $245 per person
$245
per person
Oct 23 - Oct 26
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
Great location, very comfortable beds. The lighting in the room could be better.

Reviewed on Aug 14, 2025

Don't see what you're looking for?
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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
$189 nightly
The price is $211 total per night from Aug 24 to Aug 25
$211 total
Aug 24 - Aug 25
Total with taxes and fees
8.6/10 Excellent! (134 reviews)
Short Stay
"Everything went smoothly, but for the noisy air conditioning system and the very noisy toilet!!! Other than that nice, clean, no disturbances at all."

Reviewed on Jun 25, 2025

Chocksett Inn and Restaurant
Courtyard by Marriott Boston Natick

Courtyard by Marriott Boston Natick

3 out of 5
342 Speen St, Natick, MA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $115 total per night from Aug 31 to Sep 1
$115 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Was a very quiet stay"

Reviewed on Aug 17, 2025

Courtyard by Marriott Boston Natick
Courtyard by Marriott Boston Marlborough

Courtyard by Marriott Boston Marlborough

3 out of 5
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Aug 28 to Aug 29
$142 total
Aug 28 - Aug 29
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Had a good stay"

Reviewed on Aug 18, 2025

Courtyard by Marriott Boston Marlborough
See all 356 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.

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Frequently asked questions

How much does a Sterling vacation package cost?
You'll find cheap prices from $180 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.