$86 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 $86 One Way, $150 Round Trip

$150 return flights and $86 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, Nov 7 - Sat, Nov 7
BOS
Boston
LEB
Lebanon
$150 Roundtrip, found 2 hours ago
$150
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Sat, Nov 7 from Boston to Lebanon, returning Sat, Nov 7, priced at $150 found 2 hours ago
Sat, Nov 7 - Sat, Nov 7
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 2 hours ago
$155
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Sat, Nov 7 from Boston to Lebanon, returning Sat, Nov 7, priced at $155 found 2 hours ago
Thu, Oct 29 - Sun, Nov 1
BOS
Boston
LEB
Lebanon
$165 Roundtrip, found 4 hours ago
$165
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Thu, Oct 29 from Boston to Lebanon, returning Sun, Nov 1, priced at $165 found 4 hours ago
Sun, Sep 27 - Wed, Oct 14
BOS
Boston
LEB
Lebanon
$175 Roundtrip, found 4 hours ago
$175
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Sun, Sep 27 from Boston to Lebanon, returning Wed, Oct 14, priced at $175 found 4 hours ago
Mon, Dec 28 - Thu, Dec 31
BOS
Boston
RUT
Rutland
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Dec 28 from Boston to Rutland, returning Thu, Dec 31, priced at $180 found 1 day ago
Mon, Jul 27 - Mon, Jul 27
BOS
Boston
LEB
Lebanon
$185 Roundtrip, found 1 hour ago
$185
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Jul 27 from Boston to Lebanon, returning Mon, Jul 27, priced at $185 found 1 hour 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
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $145 total per night from Jul 28 to Jul 29
$145 total
Jul 28 - Jul 29
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 ...
9.4/10 Exceptional! (1,261 reviews)
"It's not glamorous but it's clean, maintained and the staff are very kind and helpful. The location is great, with easy access to local towns, the state park and anything we could need."

Reviewed on Jul 24, 2026

Opens in a new windowAlign Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$479 nightly
The price is $527 total per night from Aug 16 to Aug 17
$527 total
Aug 16 - Aug 17
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
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$240 nightly
The price is $264 total per night from Aug 16 to Aug 17
$264 total
Aug 16 - Aug 17
Total with taxes and fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,007 reviews)
"It was a pleasure to stay at On the River. We thoroughly enjoyed sitting out on the deck in the evening watching the moon rise. The staff was warm, friendly, and helpful. The room was clean and comfortable. I would certainly stay there again."

Reviewed on Jul 24, 2026

Opens in a new windowOn The River Inn
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Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $145 total per night from Aug 9 to Aug 10
$145 total
Aug 9 - Aug 10
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)
"Very helpful and kind staff. Nice accommodations, comfortable and clean and well located, with some character and history."

Reviewed on Jul 20, 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

Traveling to Windsor County and need a cheap flight? Orbitz has great deals on flights to Windsor County right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

Find Low Cost Flights to Windsor County Quickly and Hassle-Free

There are many Internet sites that promise cheap Windsor County flights, but a busy, bargain-minded trip planner needs more than just budget air tickets. Not only does Orbitz offer the best deals for domestic and international air fare, but we also provide the resources and tools to help you plan your flights to Windsor County, book your lodging, and look up key attractions in Windsor County. Our easy search tools and guaranteed low prices let you budget your time and your money so you have more of both to spend on your vacation.

New Apps Make Booking Windsor County Flights Easier Than Ever

You no longer need to be sitting at your computer to find amazing Orbitz sales for flights to Windsor County now we offer cutting-edge mobile tools for many Android and iOS gadgets. These free apps allow you to run a search for discount air fare, look for special vacation packages, or check on your booked Windsor County flights from any location. Some special deals are only available for mobile customers, so be sure to take advantage of these free downloads today.

Orbitz Customers Are Truly #1

Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Windsor County or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Windsor County flights. When you need us, we’re here for you!

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 $150 to $185. 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 $86.
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.