Rutland Vacation Packages

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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.

Ready to book your vacation to Rutland?

 

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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
The price is CA $124 per night from Aug 21 to Aug 22
CA $124
CA $138 total
Aug 21 - Aug 22
includes taxes & fees
8.8/10 Excellent! (1,467 reviews)
"Front desk staff were very friendly and helpful. Beautiful property. Wonderful bakery. Very comfortable and convenient in our travels. Have stayed here several times."

Reviewed on Aug. 17, 2025

Publick House Historic Inn and Country Motor Lodge
Courtyard by Marriott Boston Marlborough

Courtyard by Marriott Boston Marlborough

3 out of 5
75 Felton St, Marlborough, MA
The price is CA $176 per night from Aug 25 to Aug 26
CA $176
CA $197 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Great room, clean- modern Tv, shower ++"

Reviewed on Aug. 18, 2025

Courtyard by Marriott Boston Marlborough
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
The price is CA $165 per night from Aug 28 to Aug 29
CA $165
CA $185 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Needs new renovation"

Reviewed on Aug. 18, 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 314 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Rutland vacation package cost?
You'll find cheap prices on Expedia for your Rutland getaway. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Rutland costs.
What are the cheapest months to go to Rutland?
To score cheap Rutland vacation packages, organize your trip outside of peak periods such as public holidays. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Rutland?
The ideal duration of your Rutland vacation depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to tick off all the top sights and explore some hidden treasures along the way.
How to find the best Rutland package deals?
Use Expedia's filter tool to find some tempting Rutland package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Rutland package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Rutland vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Rutland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Rutland?
If you have your Rutland travel dates confirmed, book as early as you can to snap up some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Rutland?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Rutland.
  2. Set your budget: Factor in costs like food, flights and transportation when calculating how much to set aside for your trip to Rutland. Then, pick a property that matches your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Decide how long to go away for: Now that you're more familiar with Rutland, you can figure out the perfect length of your vacation. Pull together a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Rutland vacation package.

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