Sterling Vacations from $511

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

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

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

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.
  • Jan 15 - Jan 18

    Club Wyndham Newport Onshore + Flight

    Downtown Newport
    3 nights
    3.0 star property
    8.8/10 - Excellent (202 reviews)
    "We made reservations for a 3 bedroom unit and the day of the reservation, without any warning, Wyndham moved us to a 2 bedroom at a completely different location that was further from town with any compensation. It is still 5 days from this change and they have not refunded any money for this change and it is impossible to reach them. BEWARE! they do not have any accountability!"
    Reviewed November 11, 2026
    Roundtrip • Houston (HOU) - Providence (PVD)
    HOU - PVD • 1 stop PVD - IAH • 1 stop
    $705
    $511
    per traveler
    found 2 hours ago
    Club Wyndham Newport Onshore
  • Jan 15 - Jan 18

    Forty 1 North + Flight

    Downtown Newport
    3 nights
    4.5 star property
    9.0/10 - Wonderful (479 reviews)
    Roundtrip • Houston (HOU) - Providence (PVD)
    HOU - PVD • 1 stop PVD - IAH • 1 stop
    Save 100% on your flight
    $1,533
    $1,063
    per traveler
    found 2 hours ago
    Forty 1 North
  • Jan 15 - Jan 18

    Club Wyndham Inn on Long Wharf + Flight

    Downtown Newport
    3 nights
    2.5 star property
    8.8/10 - Excellent (315 reviews)
    "The room was spotless. The view was beautiful. We could look out over the harbor. Everyone who worked there was very helpful and polite. We will definitely be back"
    Reviewed October 30, 2026
    Roundtrip • Houston (HOU) - Providence (PVD)
    HOU - PVD • 1 stop PVD - IAH • 1 stop
    $785
    $585
    per traveler
    found 2 hours ago
    Club Wyndham Inn on Long Wharf
  • Jan 14 - Jan 19

    The Preserve Sporting Club & Resort + Flight

    Richmond
    5 nights
    4.0 star property
    9.0/10 - Wonderful (12 reviews)
    Roundtrip • Houston (HOU) - Providence (PVD)
    HOU - PVD • 1 stop PVD - IAH • 1 stop
    Save 100% on your flight
    $4,282
    $3,269
    per traveler
    found 6 hours ago
    The Preserve Sporting Club & Resort
  • Dec 18 - Dec 23

    Chart House Inn + Flight

    Downtown Newport
    5 nights
    4.5 star property
    9.0/10 - Wonderful (160 reviews)
    "Inn keeper MIA the whole time. Amenities not available. Shower leaked in the floor."
    Reviewed November 6, 2026
    Roundtrip • Charlotte (CLT) - Providence (PVD)
    CLT - PVD • Nonstop PVD - CLT • Nonstop
    $1,450
    $1,123
    per traveler
    found 18 hours ago
    Chart House Inn

Where to stay near Sterling

Sterling, Connecticut offers a delightful blend of outdoor adventures and family-friendly experiences. Explore the charming scenery and enjoy a warm, welcoming atmosphere. Nearby cities and neighborhoods enhance your vacation with rich culture and historical vibes, ensuring a memorable getaway for all types of travelers.

Moosup

For travelers seeking a blend of outdoor adventure and family-friendly activities, Moosup offers a charming base to explore Sterling, Connecticut. Just around 1 mile away, visitors can enjoy the serene Moosup Pond Beach, the natural beauty of the Dr. Olav and Anna-Lisa Laakso Preserve, and the recreational opportunities at Moosup Park. With its inviting atmosphere and access to local attractions like nearby casinos and music concerts, Moosup is a smart choice for a memorable stay.

Sterling Hill Historic District

Experience the charm of Sterling Hill Historic District, an excellent hub for travelers with a passion for history, family, and nature who want to explore the beauty of Connecticut. This inviting neighborhood, located about 2 miles from Sterling, offers easy access to attractions like the serene Dr. Olav and Anna-Lisa Laakso Preserve, the picturesque Moosup Pond Beach, and the historic Plainfield Town Hall. Choosing Sterling Hill Historic District for your stay ensures a memorable vacation filled with local charm and rich history.

Plainfield

If you are a family traveler or seeking a weekend getaway, look no further than Plainfield, which features a diverse mix of activities like vibrant music concerts and exciting casino experiences. Visitors will enjoy exploring local attractions such as the serene Canterbury Green park, the historic Plainfield Town Hall, and the scenic Pachaug Outdoor Club. Located about 5 miles from Sterling, Plainfield offers easy access to a range of experiences, making it a smart choice for your stay.

Central Village

Immerse yourself in Central Village, where families and nature enthusiasts can easily access beautiful sites like Moosup Pond Beach, the serene Canterbury Green, and the historic Plainfield Town Hall. With a steady flow of visitors year-round, especially peaking from July to September, this charming village offers an eco-friendly escape. Located about 4 miles from Sterling, Central Village makes for a smart choice for your next vacation, blending outdoor adventure with budget-friendly accommodations.

Greene

Looking for the perfect spot? Greene is ideal for travelers seeking a weekend getaway, family fun, and outdoor adventures with its beautiful nature reserve, inviting parks, and the serene Pitch Pine Grove Picnic Area. Visitors can also explore the historic University of Rhode Island and enjoy the local charm of the Sterling Public Library. Situated about 4 miles from Sterling, Greene offers a smart choice for hotel bookings, ensuring a memorable stay filled with diverse experiences.

Discover the most popular places to visit in Sterling

Sterling Hotel Deals

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.

Frequently Asked Questions

How much does a Sterling vacation package cost?

You'll find cheap prices from $511 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.

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