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.
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,006 reviews)
Well designed, clean and comfortable! Convenient location.

Reviewed on Apr. 30, 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
Jul. 26 - Jul. 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (234 reviews)
Beautiful accommodations and unique character

Reviewed on Nov. 6, 2024

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (459 reviews)
This was a cute cozy little suite! It was perfect for a small girls trip getaway! The only thing missing was a microwave in the room. It was nice to have access extra towels and blankets available without calling to have them brought. Staff was kind and friendly!

Reviewed on Apr. 24, 2025

The Beverly

The Beverly

3 out of 5
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (277 reviews)
Communication was fantastic.

Reviewed on Feb. 27, 2025

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
per person
Jul. 10 - Jul. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
7.4/10 Good! (525 reviews)
I was charged 25 dollars for parking in the hotel parking lot ...wich felt like a trap considering i dont remember any notification about parking charges nor were there very many options for parking around the hotel because of congestion in that area...very disappointing...especially cause i wasnt aware and able to budget for that cost.

Reviewed on Apr. 27, 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 $261 per night from May 5 to May 6
CA $261
CA $286 total
includes taxes & fees
May 5 - May 6
8.6/10 Excellent! (127 reviews)
"This place reminded me of the Dragonfly Inn on Gilmore Girls. Our room was large and clean. The bathroom was massive! The staff was friendly. We loved the fireplace in the lobby. The exterior was gorgeous. The town is really cute too."

Reviewed on Apr. 5, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from May 14 to May 15
CA $247
CA $329 total
includes taxes & fees
May 14 - May 15
8.4/10 Very Good! (958 reviews)
"I love to see all the lifesaver everywhere doing their work. While I was observing them I noticed that nothing distracted them."

Reviewed on Apr. 29, 2025

Great Wolf Lodge Boston / Fitchburg, MA
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 $175 per night from Jun. 1 to Jun. 2
CA $175
CA $196 total
includes taxes & fees
Jun 1 - Jun 2
8.4/10 Very Good! (1,006 reviews)
Decent Stay
"This was a nice hotel. Fairly clean though the carpet smelled disgusting in our room. My friend somehow couldn’t smell it so I didn’t want to make it an issue but it was so unbearable to me that I couldn’t even eat in there without gagging. I bought carpet deodorizing powder and sprinkled it all ..."

Reviewed on Apr. 28, 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 349 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 $983 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.