Windham Vacations from $557

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $638, price is now $557 per person
$557
per person
Jul 11 - Jul 15
found 7 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
6.6/10 (1,001 reviews)
The room was very clean. The staff was pleasant and helpful. Parking was very convenient. The breakfast was beyond adequate - waffles. boiled eggs, breads and pastry and fresh fruit in a very pleasant room.

Reviewed on May 29, 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 $2,156, price is now $2,001 per person
$2,001
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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

Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,021, price is now $964 per person
$964
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
9.2/10 Wonderful! (66 reviews)
Such a beautiful time, So clean, and cozy. Such a beautiful, peaceful, and romantic place. Very enchanting, and the owner is so kind, and caring. Def cant wait to go back again.

Reviewed on Jan 4, 2026

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $895, price is now $853 per person
$853
per person
Jul 11 - Jul 15
found 7 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (93 reviews)
Will definitely be back!!

Reviewed on Apr 5, 2026

Don't see what you're looking for?
See all available trips from Columbus to Windham
View all trips

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

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
$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! (846 reviews)
"Wonderful!"

Reviewed on May 31, 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
$106 nightly
The price is $117 total per night from Jul 2 to Jul 3
$117 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 2,639 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windham vacation package cost?
You can pick up a vacation package to this destination from $557 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.