Windham Vacations from $714

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
per person
Oct 8 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Rutland (RUT)
8.4/10 Very Good! (644 reviews)
Very friendly staff. Enjoyed my stay.

Reviewed on Jun 25, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
per person
Oct 8 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Rutland (RUT)
9.2/10 Wonderful! (403 reviews)
Excellent. Jeanine was so kind and helpful. Really cute sitting room. Sauna was awesome. Quiet and clean!

Reviewed on May 25, 2025

Chateau Rooms

Chateau Rooms

4.5 out of 5
Save 100% on your flight
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
9/10 Wonderful! (51 reviews)
We had the property to ourselves with the exception of guests of the restaurant. Was a beautiful and relaxing weekend for my wife and I to lay in bed and reconnect.

Reviewed on Dec 19, 2024

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Oct 8 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Rutland (RUT)
8.6/10 Excellent! (1,001 reviews)
Carpets are very dirty. Appears worn and in need of an update.

Reviewed on Jul 14, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
per person
Sep 18 - Sep 21
found 12 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Rutland (RUT)
6.4/10 (1,003 reviews)
This property is a suitable place to stay for a place to sleep. The check in staff was friendly and it was quick. The room was equipped with basic amenities like fridge, microwave and soaps - however, the property had a distinct odor in the hallways and clearly the entire property had previously been smoked in. The level of cleanliness was lacking a bit. I would find another property the next time I am in the area.

Reviewed on Jul 13, 2025

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Windham Hotel Deals

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Windham
9.8/10 Exceptional! (48 reviews)
Great Family Home
"This was a great house for our extended family. The teenagers found plenty to do and the adults found plenty of spots to catch up. The kitchen was well stocked with equipment for our gourmet chefs.My only complaint is that there were no hangers in the closet"

Reviewed on Jul 5, 2025

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Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $120 total per night from Jul 16 to Jul 17
$120 total
Jul 16 - Jul 17
Total includes taxes and fees
6.6/10 (1,000 reviews)
Very good last-minute stay
"I booked this room last-minute but checkin was smooth, room was comfortable. I like that there are two restaurants in walking distance."

Reviewed on Jul 14, 2025

Colonial Motel And Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
$210 nightly
The price is $231 total per night from Jul 20 to Jul 21
$231 total
Jul 20 - Jul 21
Total includes taxes and fees
9.2/10 Wonderful! (777 reviews)
"Our favorite place to stay in the area"

Reviewed on Jun 20, 2025

Kimpton Taconic Hotel by IHG
See all 2,547 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 $714 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.