Windham Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SAR 390 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Windham Vacation Packages

Windham Hotel Deals

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham VT
9.8/10 Exceptional! (55 reviews)
This was our second trip to this gorgeous property, and once again, we had a wonderful time. Our group of moms were able to relax in all areas of the home, including the pool and hot tub, fire pit outside and fireplace inside, and on the beautiful deck by the outdoor kitchen. Everything was clean ...

Reviewed on 6 October 2025

Get rates
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is SAR 567 per night from Feb 2 to Feb 3
SAR 567
SAR 646 total
2 Feb - 3 Feb
includes taxes & fees
8.8/10 Excellent! (951 reviews)
Clean, nice pool and hot tub, and good price!

Reviewed on 11 January 2026

Pointe at Castle Hill Resort
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
The price is SAR 690 per night from Feb 12 to Feb 13
SAR 690
SAR 903 total
12 Feb - 13 Feb
includes taxes & fees
9.2/10 Wonderful! (825 reviews)
Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return!

Reviewed on 4 January 2026

Kimpton Taconic Hotel by IHG
See all 2,662 properties in Windham
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.

Frequently asked questions

How do I find cheap flights to Windham that have flexible change policies?
By using our neat "No change fee" filter, that's how. Simply enter your origin, destination and travel dates, click the "Search" button, then select the box directly under the "Flexible change policies" subheading (it's on the left). Expedia makes it a cinch to find inexpensive, flexible flights to Windham.
Which airlines fly to Windham?
When you're ready to reserve your seat to or near Windham, these popular airlines are waiting to welcome you on board:

  • Delta Air Lines - 3,701 flights to or near Windham each month, including 3,701 flights to Logan Intl. Airport (BOS) per month.
  • JetBlue Airways - 3,407 flights to or near Windham each month, including 3,407 flights to Logan Intl. Airport (BOS) per month.
  • American Airlines - 2,106 flights to or near Windham each month, including 2,106 flights to Logan Intl. Airport (BOS) per month.

How can I find cheap tickets to Windham?
One of the easiest ways to find cheap tickets to Windham is to be flexible with your dates. Search for your flights, then click "flexible dates" at the top of your results. It'll reveal the cheapest prices for nearby days. The lowest price for a flight to Windham in the last seven days was . Booking ahead of time will usually help you get an even better deal.
How much is a flight to Windham?
One-way flights departing from () sold for as low as in the last seven days. During this period, the cost of a return ticket to Windham ranged between and . If you find a fantastic deal, grab it fast — these fares don't hang about.
What are the most popular airports to fly into in Windham?
When you've planned where you're headed in Windham, select from these top airports:

  • Logan Intl. Airport (BOS) - 12,948 flights per month.
  • Rutland Southern Vermont Regional Airport (RUT) - 60 flights per month.

When is the cheapest time to fly to Windham?
Taking off on a Tuesday, followed by a Monday, is usually the best way to score the cheapest deal. Stay away from the weekends if possible, because Saturday is typically the most expensive day of the week. Spend the cash you saved having a good time in Windham instead!
How much is a plane ticket to Windham?
Plane fares varied from to over the last seven days. When you're ready to book, we're here to help you find a cheap flight to Windham.
What months are the cheapest to book a flight to Windham?
An excellent month to purchase affordable airfares to Windham is February. Remember that in the U.S, an expensive time to reserve a seat is during the busy month of December.
How long is a flight to Windham?
Whether or not you'll have time to watch one movie or two depends on where you're flying from in the U.S. To give you a rough idea of what to expect, here are the average flight times for three popular domestic routes to Windham:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 48 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 35 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Logan Intl. Airport (BOS) - 1 hour and 25 minutes