Windham Vacations from $697

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $785, price is now $697 per person
$697
per person
May 8 - May 11
found 9 hours ago
Roundtrip flight included
Wilmington (ILG) to Rutland (RUT)
9.2/10 Wonderful! (1,007 reviews)
Nice place close to the mountain with an attentive and friendly staff. Very clean and well run. It’s not a resort or a place where you stay to enjoy the hotel. You are here to ski / board and this is your place to return to for drinks and a good night sleep. The AC wasn’t working well when we were there but it was still late Winter so not unexpected (was unseasonably warm). The furniture in the sitting areas upstairs needs to be upgraded since that’s really the only place to hangout in morning or afternoons other than the restaurant. Overall very pleased with the place for the price.

Reviewed on Apr 2, 2026

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
Price was $815, price is now $714 per person
$714
per person
May 8 - May 11
found 9 hours ago
Roundtrip flight included
Wilmington (ILG) to Rutland (RUT)
8/10 Very Good! (1,010 reviews)
Clean room, convenient location

Reviewed on Apr 6, 2026

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

2 out of 5
Save 100% on your flight
Price was $6,436, price is now $5,715 per person
$5,715
per person
May 8 - May 11
found 9 hours ago
Roundtrip flight included
Wilmington (ILG) to Rutland (RUT)
No reviews
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $788, price is now $705 per person
$705
per person
May 8 - May 11
found 9 hours ago
Roundtrip flight included
Wilmington (ILG) to Rutland (RUT)
8.6/10 Excellent! (1,003 reviews)
Bar is a great touch!

Reviewed on Apr 1, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $996, price is now $894 per person
$894
per person
May 8 - May 11
found 9 hours ago
Roundtrip flight included
Wilmington (ILG) to Rutland (RUT)
4/10 (2 reviews)
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

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Windham Hotel Deals

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$144 nightly
The price is $156 total per night from Apr 9 to Apr 10
$156 total
Apr 9 - Apr 10
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Have stayed here many times. Close to town and Okemo. Very convenient.

Reviewed on Mar 30, 2026

Pointe at Castle Hill Resort
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $93 total per night from Apr 27 to Apr 28
$93 total
Apr 27 - Apr 28
Total with taxes and fees
6.8/10 (1,003 reviews)
Older motel style not fancy. Good hot tub in pool area. Ok for overnight on a budget.

Reviewed on Apr 6, 2026

Colonial Motel And Spa
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $160 total per night from Apr 19 to Apr 20
$160 total
Apr 19 - Apr 20
Total with taxes and fees
9.6/10 Exceptional! (1,008 reviews)
Great breakfast and excellent location.

Reviewed on Apr 5, 2026

Hampton Inn and Suites Manchester
See all 2,679 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 $697 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.