Sterling Vacations from $914
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Your Sterling Vacation
Build a custom vacation package to Sterling and prepare to experience this city how you want. Think about spending some time in the neighborhood of Killingly, which is great for nature and much more. In the mood to explore the sights but not sure where to start? Every trip to Sterling should include Moosup Pond Beach. Check out Expedia's wide range of travel options and book your dream vacation to Sterling now.
The Latest Sterling vacation packages
Price found within the past 48 hours. Click for updated prices.
The Underwood-Hale House
College Hill
$1,031
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Providence (PVD)
9.6/10 Exceptional! (116 reviews)
We loved our stay and would highly recommend to anyone in the area! Beautiful home and incredible apartment, just perfect. Would stay here every time if available!
The only slight thing I'd recommend to the host is to clarify where the main entry door is as we walked around the place and weren't quite sure. Then once we entered, we went up the wrong inside staircase with suitcases before realizing we weren't in the right place. Small potatoes and easy to remedy.
Overall 10+!!
Reviewed on Sep 17, 2026
Stay near popular Sterling attractions
Sterling Public Library
After visiting Sterling Public Library, make a plan to see the other sights and activities in Sterling. Make some time to visit the shops while you're in the area.
Dr. Olav and Anna-Lisa Laakso Preserve
You can take time to visit Dr. Olav and Anna-Lisa Laakso Preserve during your travels to Sterling. Make some time to visit the shops while you're in the area.
Pitch Pine Grove Picnic Area
After visiting Pitch Pine Grove Picnic Area, make a plan to see the other sights and activities in Sterling. Make some time to visit the shops while you're in the area.
Sterling Hotel Deals
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$92 nightly
$106 total
Oct 19 - Oct 20
Total with taxes and fees
8.4/10 Very Good! (552 reviews)
"We were pleasantly surprised at how nice this inn was. Very quaint, clean and comfortable. The front desk clerk was very helpful at giving us dinner recommendations. We did not eat the complimentary breakfast."
Reviewed on Sep 18, 2026
The Fox Tower at Foxwoods
350 Trolley Line Blvd Mashantucket CT
Fully refundableReserve now, pay when you stay
$158 nightly
$182 total
Oct 19 - Oct 20
Total with taxes and fees
Hilltop Inn and Suites, near Foxwoods Casino
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
$92 nightly
$106 total
Sep 20 - Sep 21
Total with taxes and fees
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.
Find the Best Sterling Vacation Packages
Sterling Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | T.F. Green Airport (PVD) |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Moosup Pond Beach, Prudence Crandall Museum and Haul of Fame Museum |
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Frequently asked questions
How much does a Sterling vacation package cost?
You'll find cheap prices from $914 on Expedia for your Sterling getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Sterling costs.
What are the cheapest months to go to Sterling?
If you're hoping to score a cheap Sterling vacation package, consider traveling in October, November and December. You'll typically find lower rates on accommodations and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Sterling?
With a well-organized travel plan, you can easily visit the main Sterling sights in a handful of days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Sterling vacation for longer.
How to find the best Sterling package deals?
Finding a cheap Sterling package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Sterling package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Sterling vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging accommodations and flights individually. Better still, you can customize your Sterling getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Sterling?
If you're considering an impromptu Sterling trip, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Sterling vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Sterling break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
