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.
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
Seaport District
per person
Oct 5 - Oct 8
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (2,411 reviews)
Great location in the Seaport area of Boston. The property is clean and the staff was excellent. The only issue I had was that breakfast was served only until 9 am. While this isn’t a big deal it did cause quite the chaos with guests all coming around the same time causing long lines and difficulty finding a place to sit. Having breakfast open until at least 10 am or even 11 am would mitigate this.

Reviewed on Jul. 25, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on Jul. 23, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Oct 10 - Oct 13
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
Aug 27 - Sep 3
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.8/10 Excellent! (1,009 reviews)
Beautiful hotel in a great location

Reviewed on Jul. 18, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Aug 27 - Sep 3
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Staff was excellent. Room was clean and spacious but, there was no ventilation in the bathroom. That really sucked...

Reviewed on Jul. 24, 2025

Ready to book your vacation to Sterling?

 

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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 $258 per night from Jul 27 to Jul 28
CA $258
CA $288 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (132 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
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd, Framingham, MA
Fully refundable
The price is CA $130 per night from Jul 27 to Jul 28
CA $130
CA $140 total
Jul 27 - Jul 28
includes taxes & fees
6.8/10 (1,013 reviews)
"Close to highway."

Reviewed on Jul. 23, 2025

Motel 6 Framingham, MA - Boston West
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
The price is CA $162 per night from Aug 24 to Aug 25
CA $162
CA $181 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,018 reviews)
"Great stay, location and breakfast!"

Reviewed on Jul. 22, 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 354 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Sterling vacation package cost?
You can grab a vacation package to this popular destination from CA $963 on Expedia. But how much your vacation to Sterling costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Sterling?
The off-season is the best time to visit Sterling if you're hoping to keep costs down. Another tip for finding cheap Sterling vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Sterling?
Usually, a handful of days is enough to go to the major attractions during your Sterling vacation. However, if you prefer to have some time to chill out or take day tours, think about extending your trip.
How to find the best Sterling package deals?
Bagging a cheap Sterling package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Sterling package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Sterling vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can personalize your Sterling getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Sterling?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Sterling getaway.
How to plan a trip to Sterling?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the activities on offer will also help you decide when to vacation in Sterling.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will probably be the biggest expense during your trip to Sterling.
  3. Work out your trip length: Consider how long you'd like to spend discovering Sterling. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Sterling vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.