
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.



Hotel 1620 Plymouth Harbor
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


Parker Beach Lodge
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
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.
Sterling Hotel Deals

Chocksett Inn and Restaurant
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

Courtyard by Marriott Boston Natick
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 Marlborough
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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.