$66 Cheap flights to Windsor County

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Top places to visit in Windsor County

A wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'
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Woodstock

Woodstock

Cheap flights to Windsor County from $66 One Way, $135 Round Trip

$135 return flights and $66 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 1 - Thu, Jan 7
BOS
Boston
LEB
Lebanon
$135 Roundtrip, found 13 hours ago
$135
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Lebanon, returning Thu, Jan 7, priced at $135 found 13 hours ago
Fri, Jan 1 - Thu, Jan 7
BOS
Boston
LEB
Lebanon
$145 Roundtrip, found 13 hours ago
$145
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Lebanon, returning Thu, Jan 7, priced at $145 found 13 hours ago
Mon, Nov 16 - Mon, Nov 16
BOS
Boston
RUT
Rutland
$154 Roundtrip, found 3 days ago
$154
Roundtrip
found 3 days ago
Select Cape Air flight, departing Mon, Nov 16 from Boston to Rutland, returning Mon, Nov 16, priced at $154 found 3 days ago
Fri, Dec 11 - Mon, Dec 14
BOS
Boston
LEB
Lebanon
$155 Roundtrip, just found
$155
Roundtrip
just found
Select Cape Air flight, departing Fri, Dec 11 from Boston to Lebanon, returning Mon, Dec 14, priced at $155 just found
Wed, Dec 2 - Sat, Dec 5
BOS
Boston
RUT
Rutland
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Dec 2 from Boston to Rutland, returning Sat, Dec 5, priced at $160 found 1 day ago
Thu, Dec 10 - Thu, Dec 10
BOS
Boston
RUT
Rutland
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Dec 10 from Boston to Rutland, returning Thu, Dec 10, priced at $164 found 1 day ago

Deals For This Weekend's Flights

Find The Perfect Hotel For After Your Flight

Score Epic Windsor County Accommodation Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
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
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
$210 nightly
The price is $231 total per night from Nov 19 to Nov 20
$231 total
Nov 19 - Nov 20
Total with taxes and fees
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in ...
Opens in a new windowJackson Gore Village, A Vail Resorts Property
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$149 nightly
The price is $163 total per night from Dec 6 to Dec 7
$163 total
Dec 6 - Dec 7
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 ...
9.2/10 Wonderful! (1,001 reviews)
"Filthy carpets and shower curtains."

Reviewed on Nov 13, 2026

Opens in a new windowOn The River Inn
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Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$167 nightly
The price is $181 total per night from Dec 16 to Dec 17
$181 total
Dec 16 - Dec 17
Total with taxes and fees
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,002 reviews)
"We booked a deluxe suite, and it was fantastic — basically a full one-bedroom apartment with a kitchen equipped with all the essentials, including a washing machine and dryer. The location is quiet and peaceful, and the property itself is clean, cozy, and well-maintained. The hotel also has great ..."

Reviewed on Nov 14, 2026

Opens in a new windowPointe at Castle Hill Resort
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

Orbitz is your one stop for guaranteed low prices on Windsor County flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Windsor County and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Windsor County Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Windsor County from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with 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 $135 to $164. 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 $66.
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.