$90 Cheap flights to Rutland County

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Top places to visit in Rutland County

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Killington

Killington
Aerial view, forest trees, woodland, deciduous temperate fog, lowland, Britain, UK, England, sunset Sunrise. Aerial views of woodland and forested deciduous alpine trees during early Autumn. Farmer
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Rutland

Rutland
Lake Bomoseen
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Castleton

Castleton

Cheap flights to Rutland County from $90 One Way, $174 Round Trip

$174 return flights and $90 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, Feb 5 - Fri, Feb 5
BOS
Boston
RUT
Rutland
$174 Roundtrip, found 16 hours ago
$174
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Fri, Feb 5 from Boston to Rutland, returning Fri, Feb 5, priced at $174 found 16 hours ago
Thu, Feb 4 - Sun, Feb 7
BOS
Boston
RUT
Rutland
$180 Roundtrip, found 16 hours ago
$180
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Thu, Feb 4 from Boston to Rutland, returning Sun, Feb 7, priced at $180 found 16 hours ago
Thu, Jun 25 - Sun, Jun 28
BOS
Boston
RUT
Rutland
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Jun 25 from Boston to Rutland, returning Sun, Jun 28, priced at $183 found 6 days ago
Sun, Jul 12 - Wed, Jul 15
BOS
Boston
RUT
Rutland
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jul 12 from Boston to Rutland, returning Wed, Jul 15, priced at $187 found 1 day ago
Thu, Jun 25 - Sun, Jun 28
BOS
Boston
RUT
Rutland
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Select Cape Air flight, departing Thu, Jun 25 from Boston to Rutland, returning Sun, Jun 28, priced at $189 found 6 days ago
Mon, May 10 - Mon, May 10
BOS
Boston
LEB
Lebanon
$190 Roundtrip, found 16 hours ago
$190
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Mon, May 10 from Boston to Lebanon, returning Mon, May 10, priced at $190 found 16 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
BOSWest LebanonJune 19 to June 22$203
BOSNorth ClarendonJune 19 to June 22$224
HPNWest LebanonJune 21 to June 22$287
JFKWest LebanonJune 19 to June 23$559
EWRWest LebanonJune 20 to June 21$640
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Rutland County Accommodation 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
$130 nightly
The price is $143 total per night from Jun 25 to Jun 26
$143 total
Jun 25 - Jun 26
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 ...
7.4/10 Good! (1,000 reviews)
"Amazing location. Friendly staff."

Reviewed on Jun 14, 2026

Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$156 nightly
The price is $172 total per night from Jun 17 to Jun 18
$172 total
Jun 17 - Jun 18
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! (1,013 reviews)
"The pool was dated and looks nothing like the photos. The breakfast, distillery and lobby look great. The rooms are new(ish) but the smell in the hallway……..like old mice and dates"

Reviewed on Jun 15, 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 refundableReserve now, pay when you stay
$117 nightly
The price is $129 total per night from Jul 2 to Jul 3
$129 total
Jul 2 - Jul 3
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 ...
8.2/10 Very Good! (1,008 reviews)
"The staff was very, very nice. Breakfast had a lot of choices. the pool and the hot tub were clean and very nice. Location was great."

Reviewed on Jun 16, 2026

Opens in a new windowComfort Inn Rutland - Killington
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Hampton Inn Rutland

Hampton Inn Rutland

2.5 out of 5
47 Farrell Rd Rutland VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from Jul 1 to Jul 2
$143 total
Jul 1 - Jul 2
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 ...
9/10 Wonderful! (1,002 reviews)
"Nice comfortable bed, nice selection of breakfast items"

Reviewed on Jun 15, 2026

Opens in a new windowHampton Inn Rutland
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 uses cutting edge mobile technology to help get you the best deals on Rutland County flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Rutland County Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Rutland County, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Rutland County can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Rutland County. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Rutland County to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with 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 $174 this week to Rutland County, and went as high as $640. Some lucky jet-setters departing Boston (BOS) managed to get their hands on one-way tickets starting from just $90.
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.