Windham Vacations from $985
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The Latest Windham vacation packages
Price found within the past 48 hours. Click for updated prices.
Mountain Green Resort
$3,997
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
The Vermont Inn
$1,847
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
9.2/10 Wonderful! (433 reviews)
Such a disappointment. The standard of amenities was very poor. Manager was very very helpful and welcoming but this did not make up for the poor plumbing ,lack of amenities
Reviewed on Oct 13, 2026
Pointe at Castle Hill Resort
$1,804
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
8.8/10 Excellent! (1,001 reviews)
This is a great place but the description is a bit deceptive. It’s right off the highway and not on the Castle grounds. In fact we never saw the castle. I booked it thinking we’d have a place to walk around and enjoy the grounds. Nope! The hotel was nice and the people were very friendly and helpful. We stayed in a suite and loved it. The fireplace and washer and dryer were exactly what we wanted and needed. I would stay here again but would just know you’re not on the castle grounds.
Reviewed on Oct 13, 2026
Windham Hotel Deals
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Windham VT
10/10 Exceptional! (67 reviews)
"We loved this property - had great amenities, location, & check in process very smooth. The host was very communicative. Would definitely recommend to others!"
Reviewed on Sep 27, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
$169 nightly
$186 total
Nov 12 - Nov 13
Total with taxes and fees
Aspen At Manchester
5669 Main Street Manchester Center VT
Fully refundableReserve now, pay when you stay
$147 nightly
$162 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (703 reviews)
"The location was perfect for shopping and dining in Manchester. Our room was clean and modern and had a nice television with streaming. Our refrigerator made a clanking noise throughout the night and one of the ice machines was not working. Grab and go breakfasts were supposed to be included, but ..."
Reviewed on Oct 13, 2026
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.
Find the Best Windham Vacation Packages
Windham Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
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Frequently asked questions
How much does a Windham vacation package cost?
You can pick up a vacation package to this destination from $985 on Expedia. However, how much your vacation to Windham costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windham?
You're likely to find lower rates and greater availability in March, April and October. Browse our cheap Windham vacation packages and you could get some excellent off-season deals.
How many days is enough for Windham?
Typically, a handful of days is enough to check out the major sights during your Windham vacation. However, if you'd like to have time to relax or go on day tours, consider extending your trip.
How to find the best Windham package deals?
Finding a cheap Windham package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Windham package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Windham vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can personalize your Windham getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Windham?
If you're considering a spontaneous Windham trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Windham vacation packages?
Your Windham break is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
