Windham Vacations from $520

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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 $567, price is now $520 per person
$520
per person
Aug 13 - Aug 15
found 21 hours ago
Roundtrip non-stop flight included
Houston (HOU) 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

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $637, price is now $558 per person
$558
per person
Aug 13 - Aug 15
found 21 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Rutland (RUT)
9.4/10 Exceptional! (940 reviews)
Great place! Amazing sunsets and lots of activities to do and a wonderful place for families with kids

Reviewed on Jun 14, 2026

Four Columns Inn

Four Columns Inn

4 out of 5
Price was $586, price is now $525 per person
$525
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
9.8/10 Exceptional! (40 reviews)
Good cereal/toast continental breakfast

Reviewed on May 9, 2026

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $573, price is now $521 per person
$521
per person
Aug 13 - Aug 15
found 21 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Rutland (RUT)
9.2/10 Wonderful! (1,008 reviews)
Great location! Very nice grounds, outside seating area. All staff very friendly. Bar and restaurant are great.

Reviewed on Jun 19, 2026

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
Price was $3,382, price is now $3,139 per person
$3,139
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9.8/10 Exceptional! (17 reviews)
We loved our visit here. John and Yvonne were wonderful. The space was clean, quiet, and truly magical. The views were second to none and the castle and other buildings are truly worth experiencing. We loved learning about the history of this place and we will certainly be back.

Reviewed on Jan 18, 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! (60 reviews)
"Incredible property, had a blast!"

Reviewed on Jun 19, 2026

Get rates
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
$226 nightly
The price is $249 total per night from Jun 23 to Jun 24
$249 total
Jun 23 - Jun 24
Total with taxes and fees
9.4/10 Exceptional! (850 reviews)
"A little overboard on the pride flags and and pushing the pride stuff on everybody but otherwise a nice place to stay"

Reviewed on Jun 12, 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
$104 nightly
The price is $114 total per night from Jul 2 to Jul 3
$114 total
Jul 2 - Jul 3
Total with taxes and fees
8.2/10 Very Good! (995 reviews)
"Room clean if just a bit worn. Sheets had better days. Helpful staff."

Reviewed on Jun 15, 2026

Hampton Inn Brattleboro
See all 2,663 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 $520 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.