Rutland Vacations from $532

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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

Gardner Inn

2 out of 5
Price was $547, price is now $532 per person
$532
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Worcester (ORH)
5.8/10 (27 reviews)
My stay was very pleasant. The room was spotless, the bed comfortable, and surprisingly quiet during the night. I LOVED the coffee which was a pleasant surprise. Overall, there are few choices in Gardner, but this was a good choice at a very reasonable price.

Reviewed on May 10, 2026

The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $732, price is now $671 per person
$671
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Worcester (ORH)
8.8/10 Excellent! (1,006 reviews)
Room was clean, the hotel location is excellent very picturesque, staff was very easy to work with

Reviewed on May 12, 2026

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Rutland Hotel Deals

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
$219 nightly
The price is $245 total per night from May 14 to May 15
$245 total
May 14 - May 15
Total with taxes and fees
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
$122 nightly
The price is $136 total per night from May 25 to May 26
$136 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Location was good for us. Easy access to I90

Reviewed on May 11, 2026

DoubleTree by Hilton Hotel Boston - Westborough
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131) Sturbridge MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $97 total per night from May 21 to May 22
$97 total
May 21 - May 22
Total with taxes and fees
9/10 Wonderful! (1,643 reviews)
Wonderful stay

Reviewed on May 12, 2026

Publick House Historic Inn and Country Motor Lodge
See all 343 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 $532 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.