Rutland County Vacation Packages

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Your Rutland County Vacation

Make planning your next big adventure easy with a Rutland County vacation package. Whether it's the cuisine, nature or something else entirely that lures you to this destination, our packages will help you experience the best of it. Your trip to Rutland County wouldn't be complete without exploring some of its most well-known cities, starting with Rutland. Some of the most popular attractions here include Killington Peak and Killington Adventure Centre. Leicester is another favourite city with Rutland County travellers. Visitors to this exciting destination love Lake Dunmore and Robert Frost Wayside Trail. Whether you're planning to travel for a week or a month, Expedia are here to help you tailor-make your next Rutland County vacation.

Top vacation destinations in Rutland County

FlightsFlightsHotelsHotels

Killington

Killington
Winter at the Falls Along Otter Creek in Brandon, Vermont
FlightsFlightsHotelsHotels

Brandon

Brandon

Top Rutland County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Streeter Mountain Farm

Streeter Mountain Farm

2 out of 5
Price was CA $846, price is now CA $739 per person
CA $739
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Lebanon (LEB)
6/10 (4 reviews)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,467, price is now CA $1,244 per person
CA $1,244
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (914 reviews)
Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!

Reviewed on Jan 30, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,380, price is now CA $1,185 per person
CA $1,185
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (847 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

Brook Road Cabin

Brook Road Cabin

3.5 out of 5
Price was CA $1,495, price is now CA $1,307 per person
CA $1,307
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Lebanon (LEB)
7.8/10 Good! (9 reviews)
Brook Road Condo

Brook Road Condo

3 out of 5
Price was CA $1,386, price is now CA $1,216 per person
CA $1,216
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Lebanon (LEB)
8.8/10 Excellent! (3 reviews)

Rutland County Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Apr 22 to Apr 23
CA $182
CA $200 total
Apr 22 - Apr 23
includes taxes & fees
7.4/10 Good! (1,002 reviews)
was put in a room next to elevator, elevator was rubbing squeeling reported to front desk, they refused to move us, noise kept us up all night long. terrible experience. she said they didn't have any other rooms and refused to move us the hotel was clearly NOT full capacity. Elevator certificate ...

Reviewed on Mar 31, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Apr 27 to Apr 28
CA $188
CA $207 total
Apr 27 - Apr 28
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Clean room, comfortable bed Great steakhouse next door

Reviewed on Mar 26, 2026

Comfort Inn Rutland - Killington
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Apr 20 to Apr 21
CA $193
CA $212 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Bar is a great touch!

Reviewed on Apr 1, 2026

North Star Lodge and Resort
See all 1,517 properties in Rutland County
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
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Frequently asked questions

How much does a Rutland County vacation package cost?
The most affordable Rutland County package is CA $739, so the trip of your dreams can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to tailor a package that fits you.
How do I get a cheap travel package to Rutland County?
Imagine all the awesome things you could do in Rutland County with extra cash in your pocket. Watch your savings stack up when you bundle your hotel and flights into a Rutland County vacation package. You have loads of choice when it comes to booking with Expedia too. In fact, you can select from more than 550 air carriers and 1,000,000 properties around the globe. Whether you're taking a break with the whole family or flying solo, planning a trip to Rutland County is better with a package.
What are the top hotels in Rutland County?
When it comes to hotels in Killington, Comfort Inn Trolley Square and Days Inn by Wyndham Rutland/Killington Area are two great options. If you're heading to Rutland, The Mountain Inn at Killington and Killington Mountain Lodge, Tapestry Collection by Hilton will make you feel right at home.
How far in advance should I book my Rutland County vacation?
It all depends on the air carrier, but you can generally look up international fares on Expedia nearly a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper ticket just weeks before their intended journey.
What does an Expedia Rutland County travel package include?
It comes down to what you're after. If you're traveling solo, you might decide to bundle flights and hotels. Taking the whole family to Rutland County? A travel package that includes rental cars, flights and hotels might be a better fit. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Rutland County travel package?
When you book your hotels, flights and car rentals together, you'll enjoy incredible discounts. Whether you're planning an island getaway in a villa or would rather stay in a fancy hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Rutland County Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're the boss! We have access to more than 550 partner airlines globally, so you have loads of choice when planning your Rutland County escape.
If I'm not able to travel, can I cancel my Rutland County vacation package?
Your situation can change without warning, so yes. You may be able to amend or cancel your Rutland County vacation package at no cost within 24 hours of booking. For bookings older than that, you can still cancel or make changes, but your hotel, car rental company or airline may charge a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.