Cheap Flights to Rutland County from $77 (2026/2027)

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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, Mar 5 - Sat, Mar 13
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 18 hours ago
$155
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Fri, Mar 5 from Logan Intl. to Lebanon Municipal, returning Sat, Mar 13, priced at $155 found 18 hours ago
Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 23 hours ago
$165
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $165 found 23 hours ago
Wed, Nov 25 - Sun, Nov 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 23 hours ago
$175
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 29, priced at $175 found 23 hours ago
Sat, Aug 29 - Sat, Aug 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 6 hours ago
$178
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sat, Aug 29 from Logan Intl. to Lebanon Municipal, returning Sat, Aug 29, priced at $178 found 6 hours ago
Thu, Oct 22 - Thu, Oct 22
BOS
Logan Intl.
LEB
Lebanon Municipal
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago
Select Cape Air flight, departing Thu, Oct 22 from Logan Intl. to Lebanon Municipal, returning Thu, Oct 22, priced at $180 found 6 days ago
Sun, Nov 1 - Sun, Nov 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 1 hour ago
$180
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 8, priced at $180 found 1 hour ago
Sat, Aug 29 - Sat, Aug 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$182 Roundtrip, found 6 hours ago
$182
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sat, Aug 29 from Logan Intl. to Lebanon Municipal, returning Sat, Aug 29, priced at $182 found 6 hours ago
Wed, Nov 25 - Sun, Nov 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$185 Roundtrip, found 23 hours ago
$185
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 29, priced at $185 found 23 hours ago
Fri, Feb 12 - Mon, Feb 15
HPN
Westchester County
LEB
Lebanon Municipal
$200 Roundtrip, found 4 days ago
$200
Roundtrip
found 4 days ago
Select Cape Air flight, departing Fri, Feb 12 from Westchester County to Lebanon Municipal, returning Mon, Feb 15, priced at $200 found 4 days ago
OriginDestinationTravel DatesFlights From*
BOSWest LebanonNovember 1 to November 7$155
BOSNorth ClarendonNovember 1 to November 8$180
HPNWest LebanonNovember 29 to December 1$230
JFKWest LebanonSeptember 17 to September 30$446
PHLNorth ClarendonNovember 14 to November 21$452
PHLWest LebanonSeptember 18 to September 21$454
CLEWest LebanonSeptember 30 to October 5$507
JFKNorth ClarendonSeptember 11 to September 13$523
CLENorth ClarendonOctober 15 to October 19$526
FLLNorth ClarendonSeptember 10 to September 15$584
EWRWest LebanonSeptember 11 to September 26$763
FLLWest LebanonSeptember 24 to September 27$770
EWRNorth ClarendonSeptember 8 to September 11$1,066
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BOSWest LebanonAugust 29 to August 29$178
PHLNorth ClarendonAugust 29 to September 1$581
JFKWest LebanonAugust 29 to August 30$596
*Prices include taxes and fees

Best Rutland County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Follansbee Inn
3.0-star property

Follansbee Inn

Oct 9 - Oct 12

3 night stay

San Juan (SJU) to Lebanon (LEB)

United • Non-stop roundtrip • Coach
Price was $800, price is now $650 per person
$650
per person
found 4 hours ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Nov 6 - Nov 11

5 night stay

Tampa (TPA) to Springfield (VSF)

Delta • Non-stop • Coach

Springfield (VSF) to Tampa (TPA)

Cape Air • Non-stop • Coach
Price was $1,627, price is now $1,234 per person
$1,234
per person
just found
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Oct 19 - Oct 23

4 night stay

Tampa (TPA) to Springfield (VSF)

Delta • Non-stop • Coach

Springfield (VSF) to Tampa (TPA)

Southwest Airlines • Non-stop • Coach
Price was $877, price is now $712 per person
$712
per person
found 19 hours ago
Don't see what you're looking for?
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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! (1,025 reviews)
"The property was clean and quiet very relaxing the pool was small but the kids had a blast the staff was friendly and the room was clean"

Reviewed on Aug 22, 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
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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
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 $155 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 March. 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. $155 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 $155 and $1,066. 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.
What can I expect on a flight to Rutland County?
The flight time and whether you choose a full-service or low-priced airline will be a major factor. If you're searching for long-haul flights to Rutland County, entertainment, drinks and food will often be included. Trying to find cheap flights for family vacations? Check out the deals from budget carriers. Usually, these airlines don't provide as many inclusions, so be prepared to pay for food and drinks.