Flights To Rutland County - Cheap Flights Starting at CA $124

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Rutland County's top cities

A skier in a red jacket and helmet on a snowy slope with trees in the background.

Killington

Flights
Killington

How Much Does it Cost To Fly To Rutland County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $261 Roundtrip, found 2 days ago
CA $261
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $261 found 2 days ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $275 Roundtrip, found 2 days ago
CA $275
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $275 found 2 days ago
Thu, Sep 3 - Tue, Sep 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $280 Roundtrip, found 9 hours ago
CA $280
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 8, priced at CA $280 found 9 hours ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $289 Roundtrip, found 2 days ago
CA $289
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $289 found 2 days ago
Thu, Sep 3 - Tue, Sep 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $293 Roundtrip, found 9 hours ago
CA $293
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 8, priced at CA $293 found 9 hours ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $303 Roundtrip, found 2 days ago
CA $303
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $303 found 2 days ago
Thu, Sep 3 - Tue, Sep 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $307 Roundtrip, found 9 hours ago
CA $307
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 8, priced at CA $307 found 9 hours ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $317 Roundtrip, found 2 days ago
CA $317
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $317 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
2.5-star property

Latchis Hotel

Sep 4 - Sep 7

3 night stay

Rochester (ROC) to Springfield (VSF)

American Airlines • Non-stop • Coach

Springfield (VSF) to Rochester (ROC)

Delta • Non-stop • Coach
Price was CA $1,137, price is now CA $986 per person
CA $986
per person
found 1 day ago
My Place Hotel-Randolph VT
2.0-star property

My Place Hotel-Randolph VT

Oct 2 - Oct 4

2 night stay

Toronto (YYZ) to Rutland (RUT)

United • Non-stop roundtrip • Coach
Price was CA $1,255, price is now CA $1,106 per person
CA $1,106
per person
found 7 hours ago
Deerfield Valley Inn
2.0-star property

Deerfield Valley Inn

Oct 9 - Oct 12

3 night stay

Toronto (YTO) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was CA $1,346, price is now CA $1,209 per person
CA $1,209
per person
found 17 hours ago
Don't see what you're looking for?
See all available trips from Rochester to Rutland County
View all trips

Travelers ❤️ These Rutland County 🏨

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
9.2/10 Wonderful! (1,027 reviews)
"Great location and very clean and cute property"

Reviewed on Aug 23, 2026

Opens in a new windowThe Mountain Inn at Killington
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
8/10 Very good! (1,008 reviews)
"the staff were very nice, the hotel needs a complete renovation top to bottom the hallways stinks and the rooms are not designed right, once you push the luggage cart thru the door , you can't get around."

Reviewed on Aug 22, 2026

Opens in a new windowComfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Book a stay at this golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7 Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
Opens in a new windowDays Inn by Wyndham Rutland/Killington Area
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.

Frequently asked questions

How much is the cheapest flight to Rutland County?
Thrifty travelers picked up a roundtrip flight to Rutland County for as little as CA $261 in the last seven days. If you spot a good bargain, book fast. Cheap deals don't wait around for long! This price was available on Travelocity for flights to Rutland County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Rutland County?
For your best chance at scoring a terrific flight deal, organize your vacation in September. According to Travelocity's direct flight demand between January and December last year, it's the most affordable time to journey to Rutland County.
How can I check my flight status to Rutland County?
There are a couple of ways to track the status of your flight. You'll find all the important information in our "Trips" portal, which is located at the top right of our homepage. Sign in or open a new account — you can then browse and make changes to your bookings whenever you please. If you're already on the go, the Travelocity app can also help you check the status of your flight to Rutland County, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Rutland County?
Snag the best deal with Travelocity — our "Flexible dates" function makes it that much easier. Enter your preferred travel dates, then hit the flexible dates box above the search results to see the prices for nearby days. CA $261 was the best price for a roundtrip flight to Rutland County in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Rutland County with Travelocity?
An amazing vacation is only a click or two away when you plan your trip with Travelocity. With a wide range of choices and competitive deals on cheap family flights, hotels, activities and more, we make it simple to find the best prices to suit your needs. You can also use our 24/7 online chat support and free cancellations on most activities and hotels throughout every stage of the process. Wander wisely with us and secure your cheap flights to Rutland County today.
How much is a flight to Rutland County on average?
Get your next dream vacation off to a great start by securing an unbeatable deal with Travelocity. In the last seven days, roundtrip flights to Rutland County cost between CA $261 and CA $317. Look through our site and secure an airfare that works with your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.