Windham Vacations from $442

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $502, price is now $442 per person
$442
per person
May 17 - May 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
8.6/10 Excellent! (1,004 reviews)
Bar and restaurant close really early and a group of guys checked in at 1am and were so loud woke us up till 3am. Flew all the from phoenix Arizona and ruined our ski trip to Killington we were so tired.

Reviewed on Feb 28, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $678, price is now $535 per person
$535
per person
May 17 - May 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (895 reviews)
Beautifully renovated resort!

Reviewed on Mar 9, 2026

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $531, price is now $458 per person
$458
per person
May 17 - May 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (1,002 reviews)
This hotel is a gem! The ambiance fits Killington to a “T” - Friendly staff and excellent customer service. Shuttle service to the slopes (5 mins) The restaurant/distillery is awesome, and breakfast with a view of the mountains!

Reviewed on Mar 8, 2026

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was $527, price is now $459 per person
$459
per person
May 17 - May 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (1,124 reviews)
Perfection in every way

Reviewed on Mar 1, 2026

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $559, price is now $502 per person
$502
per person
May 17 - May 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
8.8/10 Excellent! (999 reviews)
This hotel was overpriced but great location to mountain.

Reviewed on Mar 8, 2026

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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
10/10 Exceptional! (57 reviews)
We had the best time at this beautiful house. Very clean and perfect for a large group

Reviewed on Feb 22, 2026

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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
$135 nightly
The price is $146 total per night from Mar 17 to Mar 18
$146 total
Mar 17 - Mar 18
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
Yes

Reviewed on Mar 11, 2026

Pointe at Castle Hill Resort
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from Mar 23 to Mar 24
$149 total
Mar 23 - Mar 24
Total with taxes and fees
8.8/10 Excellent! (70 reviews)
Great location. Clunky check-in as all virtual. Hot tub, which is the reason booked was broken, saunas did not heat up, could not adjust the heat in the room, so even though we tried to turn it off it was 80’ overnight. Machine for tea also didn’t work. Clean rooms but the hot tub and heat issues ...

Reviewed on Mar 10, 2026

Hideaway Inn Mt. Snow
See all 2,677 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 $442 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.