Rutland Vacations from $552

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Your Rutland Vacation

Book a custom vacation package to Rutland and get ready to experience this interesting city your way. Think about spending some time in the neighborhood of Webster Square, which is good for cycling and tons more. Every trip to Rutland needs a well-thought-out itinerary. Fill yours with famous sights like Rutland State Park, Saint Josephs Abbey and Moore State Park. Expedia can help you escape your daily routine. Tailor your vacation to Rutland to suit your travel style, whatever that may look like.

The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.

Gardner Inn

$552

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Sacramento (SMF) to Worcester (ORH)

7.8/10 Good! (57 reviews)

Dirty floors are and had back pain from poor mattress. Lack of vending and good coffee.

Reviewed on Sep 25, 2026

The Colonial Hotel

$640

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Sacramento (SMF) to Worcester (ORH)

8.8/10 Excellent! (1,004 reviews)

Our stay was nice, king size bed was very comfortable and warm. Carpet in the rooms were well maintained, and bathrooms look new. Overall, a comfortable night!

Reviewed on Sep 25, 2026

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Stay near popular Rutland attractions

Rutland State Park

You can take time to visit Rutland State Park during your travels to Rutland.

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Rutland Hotel Deals

Extended Stay America Suites Boston Westborough Computer Dr

1800 Computer Dr Westborough MA

Fully refundableReserve now, pay when you stay

$91 nightly

$102 total

Oct 26 - Oct 27

Total with taxes and fees

Great Wolf Lodge Boston / Fitchburg, MA

150 Great Wolf Dr Fitchburg MA

$187 nightly

$209 total

Sep 27 - Sep 28

Total with taxes and fees

8.6/10 Excellent! (1,009 reviews)

"Hotel room was nice and comfortable but 3 of the attractions in the water park were closed. Would be nice to know in advance or at least provide some type of refund."

Reviewed on Sep 25, 2026

Publick House Historic Inn and Country Motor Lodge

277 Main Street (RT 131) Sturbridge MA

Fully refundableReserve now, pay when you stay

$79 nightly

$88 total

Sep 29 - Sep 30

Total with taxes and fees

See all 360 properties in Rutland

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 Rutland Vacation Packages

Rutland Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Worcester Regional Airport (ORH)
Population	2,100
Top Sights	Wachusett Mountain Ski Area, Worcester Art Museum and The Hanover Theatre for the Performing Arts

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Frequently asked questions

How much does a Rutland vacation package cost?

Offering great value package deals from $552 on Expedia, you'll be pleasantly surprised at how much a vacation to Rutland costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Rutland?

November, December and January are the best times to search for cheap Rutland vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on accommodations and flights.

How many days is enough for Rutland?

The ideal duration for your Rutland vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to hit all the main attractions and discover some hidden gems along the way.

How to find the best Rutland package deals?

Landing a cheap Rutland package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Rutland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.

Is it cheaper to book a Rutland vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Rutland vacation by choosing your favorite accommodation type, airline and car class.

When to book a vacation package to Rutland?

If you've got your Rutland travel dates finalized, book as early as you can to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.

Does Expedia offer Book Now, Pay Later Rutland vacation packages?

If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Rutland trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap 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.