Windham Vacations from $785

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $942, price is now $785 per person
$785
per person
Dec 24 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
7/10 Good! (1,003 reviews)

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $2,468, price is now $1,747 per person
$1,747
per person
Dec 24 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,200, price is now $864 per person
$864
per person
Dec 24 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (890 reviews)
This is our third visit. Always a great pleasure to stay here. -PM

Reviewed on Oct 31, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,721, price is now $2,146 per person
$2,146
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Save 100% on your flight
Price was $2,818, price is now $2,361 per person
$2,361
per person
Dec 24 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (70 reviews)
It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time.

Reviewed on Oct 15, 2026

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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 $785 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.