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.
Bluebird Dennisport

Bluebird Dennisport

3 out of 5
Price was CA $1,865, price is now CA $1,208 per person
CA $1,208
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (223 reviews)
This was an amazing location! The entire staff was nice and helpful. It is just a 10 min walk to the beach and close to many great places to eat. I can’t wait to come back!!

Reviewed on Jul 9, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $4,273, price is now CA $2,651 per person
CA $2,651
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
The staff and amenities at The Nantucket Inn were excellent. In particular, we give a 'shout out' to Balford, who went the extra mile (more than once!) to ensure that my physically challenged husband was accommodated in the best possible and most comfortable way during our transportation to/from town, and to Lisa at the front desk, who was responsive and speedy to our every request for information. Convenient access to the airport (walking-distance) was a bonus, as was the availability of delicious breakfast options (for a cost) and evening cocktails. The kiddoes enjoyed both pools. We would choose to stay here again.

Reviewed on Jul 11, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,469, price is now CA $1,614 per person
CA $1,614
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on Jul 11, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $4,510, price is now CA $2,967 per person
CA $2,967
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (720 reviews)
Beautiful area with private beach

Reviewed on Jul 11, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Price was CA $1,840, price is now CA $1,249 per person
CA $1,249
per person
Aug 29 - Sep 1
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (473 reviews)
Very happy with my stay. I had to extend my trip by a night and by the time it came to extend, this was one of the only affordable options nearby so I booked it. In the future this will be where I look first in the area because the price was right, I felt safe the entirety of my stay and my belongings were secure (which were my concerns staying at a hostel). The staff were extremely friendly and helpful and everything was clean and very comfortable! Thank you for my stay at your location!

Reviewed on Jul 10, 2026

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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 $225 per night from Jul 14 to Jul 15
CA $225
CA $251 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (170 reviews)
"The Inn is beautifully maintained on the outside. It reminded us of something you would see in a Hallmark movie. However, the inside is very dated. The elevator was out of service. Luckily we traveled light, so we were able to take our luggages up the stairs without issues. There was no A/C in the ..."

Reviewed on Jul 6, 2026

Chocksett Inn and Restaurant
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
The price is CA $211 per night from Jul 13 to Jul 14
CA $211
CA $236 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,020 reviews)
"Parking"

Reviewed on Jul 11, 2026

Great Wolf Lodge Boston / Fitchburg, MA
Best Western Royal Plaza Hotel & Trade Center

Best Western Royal Plaza Hotel & Trade Center

3 out of 5
181 Boston Post Rd W Marlborough MA
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jul 19 to Jul 20
CA $157
CA $176 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very good! (1,030 reviews)
"Weather we are on vacation or staying here for work related things we have never had a problem. The room is always clean and the employees are always on top of things. Breakfast is fun . The employees keep everything full and clean. They great us like family. We stay here a few times a year.MeLinda ..."

Reviewed on Jul 10, 2026

Best Western Royal Plaza Hotel & Trade Center
See all 414 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
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Family Vacations
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Stay near popular Sterling attractions

Davis' Farmland & Mega Maze

7.0/10 (2 reviews)
Enjoy an outing to Davis' Farmland & Mega Maze during your stay in Sterling. You can attend a sporting event while in the area.
See properties

Frequently asked questions

How much does a Sterling vacation package cost?
You can grab a vacation package to this popular destination from CA $1,208 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.

Explore a world of travel with Expedia

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