Windham Vacations from $929

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,150, price is now $929 per person
$929
per person
Mar 16 - Mar 21
found 17 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
9.2/10 Wonderful! (412 reviews)
Great experiment. Very accommodating stuff and environment.

Reviewed on Nov 29, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $3,063, price is now $2,126 per person
$2,126
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
No reviews
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $2,460, price is now $1,918 per person
$1,918
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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 $1,202, price is now $979 per person
$979
per person
Mar 16 - Mar 21
found 17 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Amenities are great!

Reviewed on Dec 29, 2025

Mt Green 1-d09 in Killington

Mt Green 1-d09 in Killington

2 out of 5
Save 100% on your flight
Price was $2,805, price is now $2,294 per person
$2,294
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
No reviews
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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 Oct 6, 2025

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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
$142 nightly
The price is $154 total per night from Jan 14 to Jan 15
$154 total
Jan 14 - Jan 15
Total with taxes and fees
8.8/10 Excellent! (942 reviews)
Nice hotel! Very friendly staff and great value compared to other accommodations.

Reviewed on Jan 4, 2026

Pointe at Castle Hill Resort
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
$211 nightly
The price is $232 total per night from Feb 4 to Feb 5
$232 total
Feb 4 - Feb 5
Total with taxes and fees
7.4/10 Good! (581 reviews)
Nicely decorated for Christmas. Helpful and attentive staff, Lack of heat in some of the public areas like near the library was an issue, but they tried by keeping the fireplace going. As a helpful hint- the fireplace area in the library was drafty and cold. You can go a long way toward fixing this ...

Reviewed on Dec 7, 2025

The Equinox Golf Resort & Spa
See all 2,643 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 $929 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.