$76 Cheap flights to Rutland County

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Top places to visit in Rutland County

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

Killington
Autumn landscape with bright colorful orange and red trees and leaves along a winding country road. Banner format
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Rutland

Rutland
A lakeside community with houses and docks.
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Castleton

Castleton

Cheap flights to Rutland County from $76 One Way, $155 Round Trip

$155 return flights and $76 one-way flights to Rutland County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Nov 5 - Wed, Nov 11
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 6 hours ago
$155
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Thu, Nov 5 from Boston to Lebanon, returning Wed, Nov 11, priced at $155 found 6 hours ago
Sun, Nov 1 - Sat, Nov 7
BOS
Boston
LEB
Lebanon
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Select Cape Air flight, departing Sun, Nov 1 from Boston to Lebanon, returning Sat, Nov 7, priced at $165 found 2 days ago
Sat, Oct 31 - Sat, Oct 31
BOS
Boston
LEB
Lebanon
$170 Roundtrip, found 3 days ago
$170
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sat, Oct 31 from Boston to Lebanon, returning Sat, Oct 31, priced at $170 found 3 days ago
Sat, Sep 12 - Sat, Sep 12
BOS
Boston
LEB
Lebanon
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Cape Air flight, departing Sat, Sep 12 from Boston to Lebanon, returning Sat, Sep 12, priced at $172 found 4 days ago
Sun, Aug 30 - Thu, Sep 3
BOS
Boston
LEB
Lebanon
$175 Roundtrip, found 3 hours ago
$175
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sun, Aug 30 from Boston to Lebanon, returning Thu, Sep 3, priced at $175 found 3 hours ago
Mon, Aug 17 - Thu, Aug 20
BOS
Boston
LEB
Lebanon
$178 Roundtrip, found 3 days ago
$178
Roundtrip
found 3 days ago
Select Cape Air flight, departing Mon, Aug 17 from Boston to Lebanon, returning Thu, Aug 20, priced at $178 found 3 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
BOSWest LebanonAugust 21 to August 24$178
BOSNorth ClarendonAugust 22 to August 30$203
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Rutland County Accommodation Deals

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $161 total per night from Aug 16 to Aug 17
$161 total
Aug 16 - Aug 17
Total with taxes and fees
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. ...
9.2/10 Wonderful! (1,016 reviews)
"Well, my review would likely have been much different had I actually been able to stay there. I was unable to make it due to a family emergency, and instead of giving me a credit (I did not ask for a refund) so I could enjoy their property at another time, they held to their 1 week cancellation ..."

Reviewed on Aug 14, 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
Fully refundable
$123 nightly
The price is $136 total per night from Aug 30 to Aug 31
$136 total
Aug 30 - Aug 31
Total with taxes and fees
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 ...
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
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $152 total per night from Aug 30 to Aug 31
$152 total
Aug 30 - Aug 31
Total with taxes and fees
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 ...
Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
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Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7 Rutland VT
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $130 total per night from Aug 23 to Aug 24
$130 total
Aug 23 - Aug 24
Total with taxes and fees
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 ...
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Rutland County

Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Rutland County or any other low fare domestic or international air travel.

Innovative Orbitz Tools for the Trip Planner on the Move

Now it is even faster to find exclusive deals and book cheap Rutland County flights from any location with our new Orbitz apps. These cutting-edge mobile tools are available free to anyone with an Android device, iPad, or iPhone. Look up Rutland County's most popular attractions, best restaurants, and entertainment venues or check on your flights to Rutland County and make changes to your itinerary while waiting in line for your latte.

Stay on Budget, Earn Miles with Bargain Rutland County Flights

You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Rutland County. That means you can rack up money-saving points and miles for future use while saving money now.

We Are Just a Phone Call Away If You Need Us

Booking, changing, or canceling your Rutland County flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Rutland County to your mobile phone or email.

Frequently asked questions

What is the best airport to fly to in Rutland County?
Rutland Southern Vermont Regional Airport (RUT) is the main entry point for this unique region. Once you've stepped out of the arrivals area, the possibilities are endless when it comes to adventuring around Rutland County.
How much is a flight to Rutland County?
Return flight prices dipped as low as $155 this week to Rutland County, and went as high as $203. Some lucky jet-setters departing Boston (BOS) managed to get their hands on one-way tickets starting from just $76.
How to book the cheapest flight to Rutland County?
Landing cheap flights to Rutland County is as simple as booking your ticket with Orbitz. But if you want to make sure you're nabbing the best flight deals around, here are some suggestions your wallet will love:

  • Consider departing from or arriving at nearby airports for a cheaper fare. Enter your preferred departure and arrival airports in the form fields, then click on the 'Nearby airports' function below. It will list the available options.
  • If you're flexible with your travel schedule, click on the 'Show flexible dates' link. It'll show the flight deals for the days around your selected departure. Fares often vary depending on what day of the week it is.
  • You can also select the 'Show options' function to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you want to fly.
  • The early bird gets the most rewarding savings, so book your tickets the moment you know your travel dates. The most affordable fares sell out first and prices normally increase as the departure date nears.
  • Bundle your hotels, flights and car rental into a package deal and enjoy discounts. Save your hard-earned dollars for things you're really excited about, like discovering every corner of Rutland County.
  • Flying during busier seasons means steep airfares. Try to travel outside of popular periods, such as Christmas, New Year's Eve and Easter.

What is the best time to book a flight to Rutland County?
If your schedule allows, purchase your tickets to Rutland County in January. This is the best month to score low airfares, closely followed by February and August. With a little planning, you're guaranteed to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Rutland County?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book a flight to Rutland County. If you want the most competitive airfares, search across those days and you could land a great flight deal.
What is the cheapest day of the week to fly to Rutland County?
According to Orbitz data from 2020, Monday is normally the best day of the week for cheap flights to Rutland County. Tuesday also offers wallet-friendly airfares, while Saturday has the highest ticket prices. Even though flying out at the weekend may be easier to organize, you'll have more money in your pocket to play with if you take off at the start of the week.
What is the cheapest month to fly to Rutland County?
If you have some wiggle room with your travel plans, consider departing in August. Orbitz data has found that this is generally the best month to take a trip if you're looking for cheap flights to Rutland County. As you would imagine, fares rise in June and flights book out quickly.
Which airlines allow free cancellation?
When you search for flights on Orbitz, select "Filter by flexible change policies." This filter will show you all the airlines offering free cancellation and no change fees. Breathe easy knowing that if your travel dates change, your reservation can too.
What do I need for the flight to Rutland County?
There is so much to plan for any big trip, so it's useful to get a little bit of help before you set out. Here are a few pointers to make sure you're organized for your flight:

  • Make sure you've got your travel papers and some identification. For international journeys, you'll require your passport. When purchasing your flights, always use the same name, birth date and gender as stated on your government-issued ID.
  • A well-stocked carry-on bag is a must-have for any lengthy flight. With at least a few hours up your sleeve, you'll probably long for something to keep you occupied on your trip to Rutland County. We recommend a good book (or trashy magazine), and something to nosh on.
  • Never mind what the season is, aircraft cabins can get a little chilly. Carry an extra layer on your journey to stay warm and comfy.

How do I get cheap first-class/business deals to Rutland County?
Experienced travelers have honed the art of finding first or business-class flights to Rutland County without the astronomical price tag. Take a leaf out of their book with these helpful hints:

  • Flexibility isn't confined to yoga. Leave some room to move around your travel dates so you can snap up cheaper airfares when they crop up.
  • Search for a low-cost carrier that offers business-class seats. They usually come with extra legroom and a glass of Champagne — but at a more affordable price.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you offer a price for a seat up the front. You can also try upgrading with points earned through a rewards program.

What is the best time to go to Rutland County?
Rutland County is a wonderful year-round vacation destination, but the most popular months are November, December and January. If you're into warmer weather, consider traveling during the summer months. Like most places in the Northern Hemisphere, the summer season kicks off June 20. Temperatures typically hover between 55 ºF and 75 ºF during the day.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.