$66 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 $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 4 days ago
$135
Roundtrip
found 4 days ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Lebanon, returning Thu, Jan 7, priced at $135 found 4 days ago
Fri, Jan 15 - Fri, Jan 15
BOS
Boston
RUT
Rutland
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Cape Air flight, departing Fri, Jan 15 from Boston to Rutland, returning Fri, Jan 15, priced at $154 found 6 days ago
Sun, Dec 13 - Wed, Dec 16
BOS
Boston
LEB
Lebanon
$155 Roundtrip, just found
$155
Roundtrip
just found
Select Cape Air flight, departing Sun, Dec 13 from Boston to Lebanon, returning Wed, Dec 16, priced at $155 just found
Thu, Nov 5 - Sun, Nov 8
BOS
Boston
RUT
Rutland
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Nov 5 from Boston to Rutland, returning Sun, Nov 8, priced at $160 found 1 day ago
Fri, Jan 1 - Fri, Jan 1
BOS
Boston
RUT
Rutland
$164 Roundtrip, found 9 hours ago
$164
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Rutland, returning Fri, Jan 1, priced at $164 found 9 hours ago
Tue, Feb 2 - Mon, Feb 8
DJT
West Palm Beach
RUT
Rutland
$456 Roundtrip, found 3 days ago
$456
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Feb 2 from West Palm Beach to Rutland, returning Mon, Feb 8, priced at $456 found 3 days 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. ...
9.4/10 Exceptional! (628 reviews)
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."

Reviewed on Oct 28, 2026

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
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $217 total per night from Dec 1 to Dec 2
$217 total
Dec 1 - Dec 2
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
$181 nightly
The price is $200 total per night from Nov 22 to Nov 23
$200 total
Nov 22 - Nov 23
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)
"A classy and comforting hotel in a beautiful riverside location. Great pool, sauna, and gym. The staff support was excellent, warm and welcoming."

Reviewed on Oct 30, 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
$169 nightly
The price is $183 total per night from Dec 1 to Dec 2
$183 total
Dec 1 - Dec 2
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 ...
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

Finding cheap flights to Windsor County is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Windsor County flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Windsor County through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Windsor County—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Windsor County flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Windsor County with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $456. 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.