$66 Cheap flights to Rutland County

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Top places to visit in Rutland County

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Killington

Killington
A winding road surrounded by autumn foliage.
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Rutland

Rutland

Cheap flights to Rutland County from $66 One Way, $135 Round Trip

$135 return flights and $66 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.

Fri, Jan 1 - Thu, Jan 7
BOS
Boston
LEB
Lebanon
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Lebanon, returning Thu, Jan 7, priced at $135 found 2 days ago
Fri, Jan 15 - Fri, Jan 15
BOS
Boston
RUT
Rutland
$154 Roundtrip, found 4 days ago
$154
Roundtrip
found 4 days ago
Select Cape Air flight, departing Fri, Jan 15 from Boston to Rutland, returning Fri, Jan 15, priced at $154 found 4 days ago
Thu, Dec 3 - Mon, Dec 7
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 10 hours ago
$155
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Thu, Dec 3 from Boston to Lebanon, returning Mon, Dec 7, priced at $155 found 10 hours ago
Thu, Dec 3 - Mon, Dec 7
BOS
Boston
LEB
Lebanon
$165 Roundtrip, found 10 hours ago
$165
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Thu, Dec 3 from Boston to Lebanon, returning Mon, Dec 7, priced at $165 found 10 hours ago
Fri, Nov 13 - Tue, Nov 17
BOS
Boston
RUT
Rutland
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Nov 13 from Boston to Rutland, returning Tue, Nov 17, priced at $170 found 1 day ago
Wed, Nov 25 - Sun, Nov 29
BOS
Boston
RUT
Rutland
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Nov 25 from Boston to Rutland, returning Sun, Nov 29, priced at $180 found 1 day ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
BOSWest LebanonNovember 7 to November 10$155
BOSNorth ClarendonNovember 6 to November 8$160
HPNWest LebanonNovember 6 to November 8$230
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Rutland County Accommodation Deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundable
$130 nightly
The price is $143 total per night from Nov 30 to Dec 1
$143 total
Nov 30 - Dec 1
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 ...
8/10 Very Good! (1,004 reviews)
"The staff is friendly and the room was ok but it was so noisy we couldn’t sleep"

Reviewed on Oct 31, 2026

Opens in a new windowComfort Inn Rutland - Killington
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
$156 nightly
The price is $172 total per night from Nov 1 to Nov 2
$172 total
Nov 1 - Nov 2
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. ...
Opens in a new windowThe Mountain Inn at Killington
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 out of 5
285 Thundering Brook Road Killington VT
$165 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this family-friendly hotel in Killington. Enjoy free breakfast, a sauna, and a 24-hour front desk. Our guests praise the helpful staff in our ...
Opens in a new windowMountain Meadows Lodge
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Mountain Sports Inn

Mountain Sports Inn

2 out of 5
813 Killington Road Killington VT
$109 nightly
The price is $120 total per night from Nov 22 to Nov 23
$120 total
Nov 22 - Nov 23
Total with taxes and fees
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Opens in a new windowMountain Sports Inn
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

Get the absolute lowest prices on flights to Rutland County by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Rutland County Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Rutland County flights.

Avoid Check-In Hassles When Traveling On Flights to Rutland County

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Rutland County flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Rutland County flight using Orbitz.

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 $135 this week to Rutland County, and went as high as $230. Some lucky jet-setters departing Boston (BOS) managed to get their hands on one-way tickets starting from just $66.
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.