Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
The price is AED 574 per night from Mar 1 to Mar 2
AED 574
AED 632 total
1 Mar - 2 Mar
includes taxes & fees
7.2/10 Good! (1,000 reviews)
Close to the resort, nice hot tub, decent room with a modern tv software for easy connections. Good price to hotel quality ratio.

Reviewed on 26 January 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
The price is AED 495 per night from Feb 22 to Feb 23
AED 495
AED 537 total
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
Environment, upgraded room and food

Reviewed on 8 February 2026

Fireside Inn & Suites West Lebanon
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
The price is AED 397 per night from Feb 10 to Feb 11
AED 397
AED 436 total
10 Feb - 11 Feb
includes taxes & fees
9.2/10 Wonderful! (1,102 reviews)
Very clean room, kind staff and excellent breakfast.

Reviewed on 6 February 2026

Align Inn Vermont
See all 2,698 properties in Windsor
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.

Discover the most popular places to visit in Windsor

Bowers Covered Bridge - Vermont

Brownsville Trail

You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area, or seek out the ski slopes.

Brownsville Trail
La rivière Otter Creek pour aller à Vergennes, Vermont.

Paradise Park

Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.

Paradise Park

Old Constitution House

You can learn about the history of Windsor with a visit to Old Constitution House. Wander the riverfront in this quaint area.

Old Constitution House

Frequently asked questions

How do I find cheap flights to Windsor that have flexible change policies?
It's as easy as can be with Expedia. Step 1: Enter your preferred dates and destination and press "Search." Next step? Check the "No change fee" box just below the "Flexible change policies" subheading on the top left of your screen. Step 3. Reserve your cheap and flexible fare to Windsor.
Which airlines fly to Windsor?
You can fly into a range of airports in or near Windsor with Cape Air. It operates 182 monthly flights to this area, including 121 to Lebanon Municipal Airport (LEB). Rutland Southern Vermont Regional Airport (RUT) a better choice for you? Cape Air provides 60 flights a month here.
How can I find cheap tickets to Windsor?
To score an amazing deal to Windsor, book well ahead. Also think about using Expedia's "flexible dates" link above your search results. This will list prices for similar time frames. In the last seven days, was the lowest price for a flight to Windsor.
How much is a flight to Windsor?
One-way flights departing from () sold for just in the last seven days. During this time, the cost of a round-trip fare to Windsor varied between and . If you spot a deal, book fast — these prices don't hang about.
What are the most popular airports to fly into in Windsor?
When it comes to figuring out which Windsor airport to use, here are your choices:

  • Lebanon Municipal Airport (LEB) - 121 flights per month.
  • Rutland Southern Vermont Regional Airport (RUT) - 60 flights per month.

When is the cheapest time to fly to Windsor?
Jetting off on a Tuesday, followed by a Monday, is usually the best way to pick up the cheapest deal. Steer clear of weekends if possible, because Saturday is typically the most expensive day. Spend the money you saved having a ball in Windsor instead!
How much is a plane ticket to Windsor?
Ticket prices ranged from to over the last seven days. When you're ready to book, we're here to help grab a low-cost flight to Windsor.
What months are the cheapest to book a flight to Windsor?
February is the most affordable month to reserve a seat for your Windsor getaway. Fares are priciest over the festive month of December, so steer clear of this time if you can.