Rutland Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.

Top Rutland Vacation Deals

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

Gardner Inn

2 out of 5
Price was CA $1,102, price is now CA $1,063 per person
CA $1,063
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Worcester (ORH)
7.8/10 Good! (81 reviews)
The room overall was ok, but the curtains were absolutely disgustingly dirty. The staff was very nice and overall, the room was fine. But looking at the dirty curtains was a real turn off to me.

Reviewed on Oct 29, 2026

The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was CA $1,383, price is now CA $1,335 per person
CA $1,335
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Worcester (ORH)
8.8/10 Excellent! (1,003 reviews)
The staff was amazing. Breakfast didn't open until 8 and was already luke warm by 8:15. Our room was clean and the beds were comfy. Our particular room was near the housekeeping office and laundry room. There was a propane oder in the hallway. We were told it was the laundry room. For the price we paid, I was expecting more.

Reviewed on Oct 27, 2026

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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 $125 per night from Nov 1 to Nov 2
CA $125
CA $139 total
Nov 1 - Nov 2
includes taxes & fees
Publick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Nov 22 to Nov 23
CA $132
CA $147 total
Nov 22 - Nov 23
includes taxes & fees
Wellsworth Hotel
Best Western Royal Plaza Hotel & Trade Center

Best Western Royal Plaza Hotel & Trade Center

3 out of 5
181 Boston Post Rd W Marlborough MA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Nov 24 to Nov 25
CA $123
CA $138 total
Nov 24 - Nov 25
includes taxes & fees
Best Western Royal Plaza Hotel & Trade Center
See all 375 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Rutland attractions

Rutland State Park

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

Frequently asked questions

How much does a Rutland vacation package cost?
You'll find cheap prices from CA $1,063 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.