Windham Vacations from $589

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $647, price is now $589 per person
$589
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
7.4/10 Good! (1,004 reviews)
Clean room , view of the golf area , very good breakfast.

Reviewed on Oct 10, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $710, price is now $652 per person
$652
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
8.6/10 Excellent! (1,003 reviews)
Friendly helpful staff Clean room Quiet

Reviewed on Oct 13, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $962, price is now $885 per person
$885
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.2/10 Wonderful! (891 reviews)
Location was convenient. The rooms were decently sized and clean. Staff was very helpful. The only thing lacking was that the room was fairly sterile looking and not warm, inviting… overall though can’t complain got a decent night of sleep.

Reviewed on Oct 14, 2025

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $743, price is now $706 per person
$706
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
8.8/10 Excellent! (888 reviews)
The place was out slightly out of town so it was quiet.

Reviewed on Oct 13, 2025

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Windham Hotel Deals

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Windham
9.8/10 Exceptional! (53 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 Oct 6, 2025

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Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $181 total per night from Nov 10 to Nov 11
$181 total
Nov 10 - Nov 11
Total with taxes and fees
7.2/10 Good! (550 reviews)
"Stayed one night. Great location and beautiful resort hotel. Check in didn’t go well with 45 min delay. They gave us drink tickets and waived the resort fee. Other than that, great stay!"

Reviewed on Oct 15, 2025

The Equinox Golf Resort & Spa
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
$205 nightly
The price is $226 total per night from Oct 19 to Oct 20
$226 total
Oct 19 - Oct 20
Total with taxes and fees
8.4/10 Very Good! (802 reviews)
"The rooms/beds/pillows very comfortable. Extra large bathroom with shower and shower/tub. Cozy, festive, lodge like grounds! 24 hr self serve coffee/water on ground floor."

Reviewed on Oct 14, 2025

Jackson Gore Village
See all 2,573 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.

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 $589 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.