Rutland Vacations from $382

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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.
Trainmasters Inn

Trainmasters Inn

3 out of 5
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Worcester (ORH)
9.6/10 Exceptional! (354 reviews)
The railroad theme throughout the property made this stay very different from any place we have stayed in over 50 years of travel.

Reviewed on Jul 27, 2025

The Colonial Hotel

The Colonial Hotel

3 out of 5
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Worcester (ORH)
8.8/10 Excellent! (1,020 reviews)
When I lost earrings staff were courteous and helpful

Reviewed on Aug 3, 2025

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Rutland Hotel Deals

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
$99 nightly
The price is $111 total per night from Aug 5 to Aug 6
$111 total
Aug 5 - Aug 6
Total includes taxes and fees
8.8/10 Excellent! (1,461 reviews)
"Love the staff, rooms and the history of the place. Only complaint was cold french fries at the tavern, second time it's happened, I reckon not too bad a problem but it's the little things."

Reviewed on Aug 2, 2025

Publick House Historic Inn and Country Motor Lodge
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
$119 nightly
The price is $133 total per night from Aug 17 to Aug 18
$133 total
Aug 17 - Aug 18
Total includes taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Great stay, location and breakfast!"

Reviewed on Jul 22, 2025

DoubleTree by Hilton Hotel Boston - Westborough
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Aug 10 to Aug 11
$133 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (1,256 reviews)
"Clean facility, very spacious"

Reviewed on Aug 1, 2025

Wellsworth Hotel
See all 312 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.

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Frequently asked questions

How much does a Rutland vacation package cost?
Offering great value package deals from $382 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.