Windham Vacations from $465
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The Latest Windham vacation packages
Price found within the past 48 hours. Click for updated prices.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
$690
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (67 reviews)
Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night.
Reviewed on Aug 15, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$595
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (865 reviews)
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 2026
Windham Hotel Deals
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Windham VT
10/10 Exceptional! (63 reviews)
"We had the absolute best time at Suki’s property. Even better than the photos, the pool, house, seclusion, outdoor dining area, all of it was perfect for our golf trip and the best summer weekend. More beds than we could count, the home was clean and very comfortable. Highly recommend!"
Reviewed on Jul 29, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$83 nightly
$91 total
Sep 1 - Sep 2
Total with taxes and fees
6.8/10 (46 reviews)
"It was dirty. The sink, bathroom, tub, floors. All dead bugs all over. TV was great. But a very musty smell in room. My sheets were not dry when we went to bed."
Reviewed on Aug 26, 2026
The Equinox Golf Resort And Spa
3567 Main Street Manchester VT
Fully refundableReserve now, pay when you stay
$223 nightly
$245 total
Sep 7 - Sep 8
Total with taxes and fees
7.4/10 Good! (660 reviews)
"The bed sunk into the middle and had no support and the shower didn’t drain so you had to shower in standing water Overall rooms were tired and needed updating Poor lighting in bathroom vanity area."
Reviewed on Aug 23, 2026
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 $465 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.
