Sterling Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Excellent hotel with friendly staff, clean and comfortable rooms with a Starbucks! We love the cookies at check in. always a winner. It is in a weird location but for our one night it was great.

Reviewed on Jul. 14, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

Ready to book your vacation to Sterling?

 

Choose your dates

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 $259 per night from Jul 15 to Jul 16
CA $259
CA $289 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (131 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 $117 per night from Jul 16 to Jul 17
CA $117
CA $127 total
Jul 16 - Jul 17
includes taxes & fees
6.8/10 (1,011 reviews)
"Solid stay. Easy late night checkin"

Reviewed on Jul. 11, 2025

Motel 6 Framingham, MA - Boston West
Great Wolf Lodge Boston / Fitchburg, MA
Great Wolf Lodge Boston / Fitchburg, MA
3.5 out of 5
150 Great Wolf Dr, Fitchburg, MA
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from Jul 15 to Jul 16
CA $272
CA $304 total
Jul 15 - Jul 16
includes taxes & fees
8.4/10 Very Good! (1,022 reviews)
"Really enjoyed the wolf den suite. Plenty of room, microwave/mini fridge in room. Free ears at gift shop after check in! Download the app before going, willow will help you with anything."

Reviewed on Jul. 13, 2025

Great Wolf Lodge Boston / Fitchburg, MA
See all 355 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 $631 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.