Windham Vacations from $459

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $622, price is now $459 per person
$459
per person
Jan 16 - Jan 19
found 7 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9/10 Wonderful! (774 reviews)
Very welcoming, spacious, clean. Perfect for a family of 4.

Reviewed on Nov 18, 2025

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Save 100% on your flight
Price was $850, price is now $671 per person
$671
per person
Jan 16 - Jan 19
found 7 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9/10 Wonderful! (1,000 reviews)
Beautiful Inn. Pretty, clean and well maintained. Close to Woodstock. Vt and shops. Highly recommend

Reviewed on Sep 30, 2025

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,737, price is now $1,400 per person
$1,400
per person
Jan 16 - Jan 19
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
No reviews
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,717, price is now $1,396 per person
$1,396
per person
Jan 16 - Jan 19
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
No reviews
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,278, price is now $1,053 per person
$1,053
per person
Jan 16 - Jan 19
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared.

Reviewed on Nov 30, 2025

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Windham Hotel Deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$186 nightly
The price is $205 total per night from Jan 5 to Jan 6
$205 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.2/10 Wonderful! (815 reviews)
Staff was great. Our room was okay… broken blinds and lots of scuffs on walls

Reviewed on Nov 16, 2025

Kimpton Taconic Hotel by IHG
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
$215 nightly
The price is $236 total per night from Dec 7 to Dec 8
$236 total
Dec 7 - Dec 8
Total with taxes and fees
7.4/10 Good! (572 reviews)
Courteous staff Clean room

Reviewed on Nov 22, 2025

The Equinox Golf Resort & Spa
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$146 nightly
The price is $159 total per night from Dec 15 to Dec 16
$159 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (920 reviews)
Loved our room. Very clean and enjoyed fireplace. Only thing we were bothered by was noise outside our room probably connected to pool heater or filter.

Reviewed on Nov 11, 2025

Pointe at Castle Hill Resort
See all 2,593 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.

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 $459 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.