Rutland Vacations from $923

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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.
Copper Lantern Motor Lodge

Copper Lantern Motor Lodge

2 out of 5
Price was $956, price is now $923 per person
$923
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Boise (BOI) to Worcester (ORH)
8.4/10 Very Good! (152 reviews)
The setting of these rooms is serene and lovely, and I especially liked having a screened, lockable "back door" that opened directly out onto the pond (beautifully misty in the morning) and allowed me to sleep with the door open and fresh cold night air streaming into the room all night long. The owner was also very welcoming and I loved that they manage to be both pet AND allergy friendly by having separate rooms for pets and no pets. A perfect balance.

Reviewed on Sep 27, 2025

The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $1,057, price is now $1,040 per person
$1,040
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Boise (BOI) to Worcester (ORH)
8.8/10 Excellent! (1,008 reviews)
It was very expensive for the time of year and area

Reviewed on Sep 26, 2025

Gardner Inn

Gardner Inn

2 out of 5
Price was $942, price is now $932 per person
$932
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Boise (BOI) to Worcester (ORH)
5/10 (8 reviews)
this is your every day hotel/motel.

Reviewed on Sep 13, 2025

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Rutland Hotel Deals

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
$127 nightly
The price is $142 total per night from Oct 27 to Oct 28
$142 total
Oct 27 - Oct 28
Total with taxes and fees
8.6/10 Excellent! (1,035 reviews)
"The room was lovely and so clean. I wish we had had more time. Lovely facility"

Reviewed on Sep 22, 2025

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
$84 nightly
The price is $94 total per night from Sep 29 to Sep 30
$94 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (1,524 reviews)
"Our room was really dated and there was a wedding here so it was a lot of partying going on in the middle of the night"

Reviewed on Sep 21, 2025

Publick House Historic Inn and Country Motor Lodge
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $161 total per night from Sep 29 to Sep 30
$161 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
Fantastic rest stop.
"Very quiet and spacious with appealing surroundings."

Reviewed on Sep 24, 2025

The Colonial Hotel
See all 311 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 $923 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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