$76 Cheap flights to Windsor County

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Top places to visit in Windsor County

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Woodstock

Woodstock

Cheap flights to Windsor County from $76 One Way, $145 Round Trip

$145 return flights and $76 one-way flights to Windsor 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.

Sat, Dec 26 - Sat, Jan 2
BOS
Boston
LEB
Lebanon
$145 Roundtrip, found 4 hours ago
$145
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Sat, Dec 26 from Boston to Lebanon, returning Sat, Jan 2, priced at $145 found 4 hours ago
Fri, Nov 6 - Sun, Nov 8
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 18 hours ago
$155
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Fri, Nov 6 from Boston to Lebanon, returning Sun, Nov 8, priced at $155 found 18 hours ago
Fri, Nov 6 - Sun, Nov 8
BOS
Boston
LEB
Lebanon
$158 Roundtrip, found 18 hours ago
$158
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Fri, Nov 6 from Boston to Lebanon, returning Sun, Nov 8, priced at $158 found 18 hours ago
Fri, Feb 5 - Mon, Feb 8
BOS
Boston
RUT
Rutland
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Feb 5 from Boston to Rutland, returning Mon, Feb 8, priced at $160 found 2 days ago
Fri, Nov 6 - Sun, Nov 8
BOS
Boston
LEB
Lebanon
$165 Roundtrip, found 18 hours ago
$165
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Fri, Nov 6 from Boston to Lebanon, returning Sun, Nov 8, priced at $165 found 18 hours ago
Sat, Oct 17 - Sat, Oct 24
RSW
Fort Myers
RUT
Rutland
$442 Roundtrip, found 2 days ago
$442
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Oct 17 from Fort Myers to Rutland, returning Sat, Oct 24, priced at $442 found 2 days ago
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Deals For This Weekend's Flights

Find The Perfect Hotel For After Your Flight

Score Epic Windsor County Accommodation Deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$142 nightly
The price is $156 total per night from Sep 16 to Sep 17
$156 total
Sep 16 - Sep 17
Total with taxes and fees
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowAlign Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$739 nightly
The price is $813 total per night from Sep 20 to Sep 21
$813 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowWoodstock Inn & Resort
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$327 nightly
The price is $360 total per night from Sep 17 to Sep 18
$360 total
Sep 17 - Sep 18
Total with taxes and fees
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions ...
9.6/10 Exceptional! (315 reviews)
"It’s an overpriced hotel with zero staff. Also it’s about a mile outside town."

Reviewed on Sep 11, 2026

Opens in a new windowThe Jackson
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Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
$145 nightly
The price is $160 total per night from Sep 20 to Sep 21
$160 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this business-friendly hotel in White River Junction. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,000 reviews)
"Great historic hotel with nice and helpful staff in the middle of town."

Reviewed on Sep 13, 2026

Opens in a new windowHotel Coolidge
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

Windsor County

End your search for discount fares on flights to Windsor County. Orbitz has all the best prices on Windsor County flights. With Orbitz, you can expect:

Cheap Deals on Flights to Windsor County

We offer big discounts and last-minute savings on Windsor County flights. We make it easy for you to research, plan, and book your flight to Windsor County — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

Travel Convenience on the Go

Get alerts, updates, or book your Windsor County flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Windsor County flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Windsor County flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Windsor County flights to the actual booking. If you want to cancel your flight to Windsor County, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Windsor County with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

Frequently asked questions

What is the best airport to fly to in Windsor County?
Rutland Southern Vermont Regional Airport (RUT) is the major entry point for this unique destination. Once you've stepped out of the terminal, the possibilities are endless when it comes to adventuring around Windsor County.
How much is a flight to Windsor County?
Lots of huge deals were up for the taking this week, with round-trip flights to Windsor County fluctuating from $145 to $442. But it was jet-setters beginning their trip from Boston (BOS) who bagged the really big bargains. One-way tickets to Windsor County started at just $76.
How to book the cheapest flight to Windsor County?
With some of the most incredible flight deals around, you can jet for less with Orbitz. The following tips and hints will help you find cheap flights to Windsor County — and leave you with more cash to play with:

  • Consider taking off from or landing at alternative airports to save money. Enter your preferred departure and arrival points in the form fields, then choose the 'Nearby airports' function below. It will list your options, if any.
  • If your travel plans aren't carved in stone, click on the 'Show flexible dates' link to compare flight deals for a variety of departure dates. You may find an amazing fare.
  • To refine your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • Once you've settled on your travel dates, don't delay booking your flight. Airfares generally climb as the departure date nears.
  • Combine your hotels, flights and car rental into a value-for-money package deal. Save your hard-earned cash for things that really excite you, like exploring every corner of Windsor County.
  • Flying during the busy season often means pricey airfares. If possible, plan your vacation outside of popular periods, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Windsor County?
Book in January, February or August for the lowest airfares to Windsor County. Once you've found a bargain, lock it in — cheap flights are known to appear and then vanish in the click of a mouse.
What day of the week is the cheapest to book a flight to Windsor County?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book flights to Windsor County. If you're after unbeatable airfares, search across those days and you could catch an excellent flight deal.
What is the cheapest day of the week to fly to Windsor County?
Based on Orbitz data from 2020, Monday tends to be the best day to get cheap flights to Windsor County. Tuesday also has more affordable airfares, whereas Saturday has the highest ticket rates. Although flying out at the weekend may be easier to arrange, you'll have more money to play with if you set off at the start of the week.
What is the cheapest month to fly to Windsor County?
If you have some wiggle room with your travel dates, think about leaving during August. Orbitz data shows that this is generally the best month to take a trip if you want cheap flights to Windsor County. As you would expect, fares get pricier in June and flights book out quickly.
Which airlines allow free cancellation?
We understand that plans change and flexibility is more important than ever. That's why you can search for flights that include free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll find you fares with more flexibility than candy in a hot car!
What do I need for the flight to Windsor County?
Whether you're a regular flyer or it's your first time in the air, it's always great to be prepared on your trip. Here are some key things to bear in mind:

  • Travel documentation such as e-tickets and identification are a must. To avoid any delays when you check in, make sure your booking is made with the exact name, birth date and gender as indicated on your government-issued ID.
  • A properly packed carry-on bag is the key to a comfortable flight experience. Given your flight to Windsor County is no quick hop, take some snacks and things to keep you happy. Something to read or listen to is sure to help the hours pass.
  • Both air conditioning and high altitudes can create a chilly environment. No matter what the weather is outside, carry a sweater with you to keep nice and warm during the journey.

How do I get cheap first-class/business deals to Windsor County?
There are ways of booking business or first-class tickets to Windsor County that won't burn through your wallet. Claim a seat in the pointy end of the plane for less with these great tips:

  • Be more flexible with your travel dates and wait for exclusive offers or sales on first or business-class airfares.
  • Low-cost airlines offer business-class seating at a fraction of the usual cost. Ditch the full-service carriers and book with one of these cheaper options.
  • Bid for an upgrade in online auctions (if available) or upgrade through your loyalty program.

What is the best time to go to Windsor County?
If you'd like to soak up the culture of Windsor County in the tourist season, January, June and August are the best months to visit. June 20 signals the start of the summer season in the Northern Hemisphere and is a perfect time to travel if you relish the outdoors. Around this time of the year, average daily temperatures generally range from 55 ºF to 75 ºF.

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.