Rutland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Your Rutland Vacation
Pick a Rutland vacation package and focus on what counts — having fun. This means no more planning headaches, just lots more time to immerse yourself in the delights of this interesting city, such as its laid-back lifestyle and spectacular views. A trip to Rutland is a great opportunity to take in the sights. Be sure to stop by big-name attractions such as Paramount Theater, Vermont State Fairgrounds and Rutland Country Club. Don't put off your visit to this destination any longer. Your ultimate Rutland vacation is only a few clicks away with Expedia.
Top Rutland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Greenbrier Inn
CA $1,003
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.4/10 Exceptional! (686 reviews)
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on Aug 3, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
CA $1,219
per person
Oct 1 - Oct 4
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9/10 Wonderful! (865 reviews)
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 2026
Ready to book your vacation to Rutland?
Rutland Hotel Deals
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundable
CA $188
CA $207 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,010 reviews)
"Place is falling apart. Just look at the elevator. Rooms need to be updated. Has a weird smell to the room. Breakfast was awful"
Reviewed on Aug 26, 2026
Days Inn by Wyndham Rutland/Killington Area
401 US-7 Rutland VT
Fully refundableReserve now, pay when you stay
CA $163
CA $180 total
Aug 30 - Aug 31
includes taxes & fees
Hampton Inn Rutland
47 Farrell Rd Rutland VT
Fully refundableReserve now, pay when you stay
CA $197
CA $217 total
Sep 6 - Sep 7
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Excellent location and delicious breakfast! Friendly staff"
Reviewed on Aug 25, 2026
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.
Stay near popular Rutland attractions
Paramount Theater
8.6/10 (46 reviews)
You can enjoy a show at Paramount Theater during your stay in Rutland. Discover the area's mountain views, or seek out its ski slopes.
Vermont State Fairgrounds
8.2/10 (39 reviews)
Enjoy an outing to Vermont State Fairgrounds during your stay in Rutland. Discover the area's mountain views, or seek out its ski slopes.
Pine Hill Park
8.4/10 (16 reviews)
Enjoy the mountain views and explore Pine Hill Park, a lovely green space in Rutland. You can seek out the ski slopes while in the area.
Green Mountain Shopping Plaza
You can do some window-shopping at Green Mountain Shopping Plaza during your trip to Rutland. Make time for the shops and ski slopes in this family-friendly area.
Rutland Country Club
8.4/10 (15 reviews)
Play a round of golf in Rutland at Rutland Country Club, and enjoy other activities such as skiing. Discover the mountain views while you're in the area.
Hathaway Farm
8.4/10 (7 reviews)
Enjoy an outing to Hathaway Farm during your stay in Rutland. Discover the area's mountain views, or seek out its ski slopes.
Bucklin Trailhead
9.0/10 (2 reviews)
Enjoy the mountain views and explore Bucklin Trailhead, a lovely green space in Mendon. You can seek out the ski slopes while in the area.
McLaughlin Falls
8.8/10 (9 reviews)
Explore the lovely green spaces of McLaughlin Falls and enjoy the ski slopes in Mendon. Discover the mountain views while you're in the area.
Frequently asked questions
How much does a Rutland vacation package cost?
You'll find cheap prices from CA $1,003 on Expedia for your Rutland getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Rutland costs.
What are the cheapest months to go to Rutland?
If you're hoping to snag a cheap Rutland vacation package, consider travelling in May, June and November. You're likely to find better prices on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Rutland?
With a well-organized schedule, you can easily visit the top Rutland sights in a few days. But if you'd like to discover hidden gems or go on day trips, think about booking your Rutland vacation for longer.
Is it worth booking a vacation package to Rutland?
Rutland offers everything you need for an unforgettable trip. Get your Rutland vacation off to a flying start by checking out popular attractions like Diamond Run Mall.
How to find the best Rutland package deals?
Finding a cheap Rutland package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Rutland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Rutland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still get the freedom to create a personalized Rutland vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Rutland?
Land amazing discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Rutland escape.
How to plan a trip to Rutland?
- Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Rutland.
- Set your budget: Factor in costs like flights, meals and transportation when working out how much to save for your trip to Rutland. Then, pick a hotel that works with your budget, whether that's a low-cost stay or a more luxurious getaway.
- Work out your trip length: Think about how much time you want to spend discovering Rutland. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your airfare and accommodations: Once you've settled on your dates and duration, book the ideal Rutland vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
