Windham Vacations from $464

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The Latest Windham vacation packages

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

The Putney Inn

2.5 out of 5
Price was $512, price is now $464 per person
$464
per person
Jul 16 - Jul 19
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
Only coffee available for breakfast. Room smelled horrible and it was dirty collecting dust and dirty behind curtain. Fyi:: if you like to sleep in dark room bring your own black out curtains. Towels where dirty and very dingy. . Restaurant closes at 3 and nothing close by where to get a decent meal. Won't be staying there again.

Reviewed on May 29, 2026

Harvest Barn Inn

Harvest Barn Inn

3 out of 5
Price was $620, price is now $525 per person
$525
per person
Jul 16 - Jul 19
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
9.8/10 Exceptional! (266 reviews)
Excellent hosts provided a terrific stay!

Reviewed on May 14, 2026

Four Columns Inn

Four Columns Inn

4 out of 5
Price was $699, price is now $664 per person
$664
per person
Jul 16 - Jul 19
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
9.8/10 Exceptional! (39 reviews)
Good cereal/toast continental breakfast

Reviewed on May 9, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $3,296, price is now $3,250 per person
$3,250
per person
Aug 8 - Aug 10
found 17 hours ago
Roundtrip flight included
San Jose (SJC) to Rutland (RUT)
8.8/10 Excellent! (1,000 reviews)
Amazing hot pool, great staff, another marvelous stay very close to the mountain and plenty of other activities. Laundry room is clutch (coin operated machines, change available at front desk). The wife had an injury and wasn't able to navigate stairs all that well, the front desk was understanding and were kind enough to move our room to the main floor, requiring no stairs, while the elevator was being worked on. New ownership is busy making some upgrades and maintenance and hopefully the vibes will remain the same as we've loved for years!

Reviewed on May 28, 2026

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $3,282, price is now $3,236 per person
$3,236
per person
Aug 8 - Aug 10
found 17 hours ago
Roundtrip flight included
San Jose (SJC) to Rutland (RUT)
9.2/10 Wonderful! (1,002 reviews)
They definitely have a moisture problem which is why they have dehumidifiers every 30 ft. The rooms are musty which is why they machines in the rooms. Breakfast was not great. The location was good.

Reviewed on Jun 6, 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! (59 reviews)
"amazing stay! highly recommend Close to several golf courses (MT Snow & Stratton) and this amazing diner (Maple Leaf)"

Reviewed on May 29, 2026

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Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$204 nightly
The price is $224 total per night from Jun 14 to Jun 15
$224 total
Jun 14 - Jun 15
Total with taxes and fees
9.4/10 Exceptional! (848 reviews)
"dirty room and overcapacity. No breakfast"

Reviewed on Jun 2, 2026

Kimpton Taconic Hotel by IHG
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $121 total per night from Jul 2 to Jul 3
$121 total
Jul 2 - Jul 3
Total with taxes and fees
8.2/10 Very Good! (989 reviews)
"We had a reat stay. Hotel was vey clean and staff was. Very helpful"

Reviewed on Jun 1, 2026

Hampton Inn Brattleboro
See all 2,613 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 $464 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.