Sterling Vacation Packages

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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.

Top Sterling Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lakeside Inn
Boston Harbor Hotel
Raffles Boston
Studio Allston Hotel
Sesuit Harbor House

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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
The price is CA $260 per night from Aug 31 to Sep 1
CA $260
CA $290 total
Aug 31 - Sep 1
includes taxes & 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
The price is CA $142 per night from Sep 4 to Sep 5
CA $142
CA $159 total
Sep 4 - Sep 5
includes taxes & fees
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
The price is CA $162 per night from Sep 4 to Sep 5
CA $162
CA $181 total
Sep 4 - Sep 5
includes taxes & fees
Courtyard by Marriott Boston Marlborough
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.