$67 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 $67 One Way, $135 Round Trip

$135 return flights and $67 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.

Fri, Jan 8 - Wed, Jan 13
BOS
Boston
LEB
Lebanon
$135 Roundtrip, found 12 hours ago
$135
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Fri, Jan 8 from Boston to Lebanon, returning Wed, Jan 13, priced at $135 found 12 hours ago
Thu, Dec 24 - Fri, Jan 1
BOS
Boston
LEB
Lebanon
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Dec 24 from Boston to Lebanon, returning Fri, Jan 1, priced at $145 found 1 day ago
Wed, Dec 9 - Thu, Dec 17
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Dec 9 from Boston to Lebanon, returning Thu, Dec 17, priced at $155 found 1 day ago
Wed, Nov 25 - Sun, Nov 29
BOS
Boston
LEB
Lebanon
$158 Roundtrip, found 8 hours ago
$158
Roundtrip
found 8 hours ago
Select Cape Air flight, departing Wed, Nov 25 from Boston to Lebanon, returning Sun, Nov 29, priced at $158 found 8 hours ago
Fri, Jan 1 - Thu, Jan 7
BOS
Boston
RUT
Rutland
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Rutland, returning Thu, Jan 7, priced at $160 found 2 days ago
Wed, Feb 17 - Sun, Feb 21
JFK
New York
RUT
Rutland
$488 Roundtrip, found 5 days ago
$488
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Feb 17 from New York to Rutland, returning Sun, Feb 21, priced at $488 found 5 days ago
Sat, Mar 13 - Tue, Mar 16
CLT
Charlotte
RUT
Rutland
$616 Roundtrip, found 11 hours ago
$616
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Mar 13 from Charlotte to Rutland, returning Tue, Mar 16, priced at $616 found 11 hours ago

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
$206 nightly
The price is $226 total per night from Oct 18 to Oct 19
$226 total
Oct 18 - Oct 19
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
$689 nightly
The price is $758 total per night from Oct 27 to Oct 28
$758 total
Oct 27 - Oct 28
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. ...
9.4/10 Exceptional! (611 reviews)
"Our 2nd floor room with balcony was beautiful, large, clean, and with excellent amenities, also looking over the waterfront. The bed was very comfortable. We enjoyed breakfast each morning very much. Our server is friendly and helpful. We were able to get close-in parking. Desk staff were also friendly. ..."

Reviewed on Sep 27, 2026

Opens in a new windowWoodstock Inn & Resort
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$248 nightly
The price is $273 total per night from Oct 26 to Oct 27
$273 total
Oct 26 - Oct 27
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! (323 reviews)
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."

Reviewed on Sep 27, 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
$131 nightly
The price is $144 total per night from Oct 26 to Oct 27
$144 total
Oct 26 - Oct 27
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! (1,002 reviews)
"Old with spiders."

Reviewed on Sep 26, 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

Why search for low cost fares on your flights to Windsor County when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Windsor County

Orbitz offers massive discounts and substantial last-minute savings on your Windsor County flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Windsor County flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Windsor County. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Windsor County but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

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 $135 to $616. 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 $67.
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.