Windham Vacations from $867
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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
$867
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
6.8/10 (1,002 reviews)
TV did not work, was told no one was there to fix. Bathroom floor in room was dirty needed to be swept, tub did not drain.
Reviewed on Sep 23, 2026
Greenbrier Inn
$1,035
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.4/10 Exceptional! (685 reviews)
Very clean and charming inn. Spacious room. We were greeted on arrival and as we were there for a Spartan race early in the morning, the host said that he would put breakfast out early for us. The continental breakfast contained many options. We will definitely be returning!
Reviewed on Sep 20, 2026
The Vermont Inn
$1,280
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.2/10 Wonderful! (431 reviews)
We arrived to find the place in total disarray. The lobby was full of old furniture that was to be sold the next day in an estate sale. This was not communicated to us in the reservation. The rooms were clean, yet bare of any furniture to sit on besides the bed. My room smells of terrible cologne and I had to wash everything when I got home. The entire place was rundown and a bit scary. We were given a $50 refund, but deserve more! These kinds of things need to be communicated about so we have a choice. They made a quick buck off of us.
Reviewed on Sep 19, 2026
Windham Hotel Deals
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Windham VT
10/10 Exceptional! (65 reviews)
"We had a wonderful 7-night stay at this beautiful private retreat!!! Everything was top-notch … from the owner’s communication to the accommodations and property. We especially enjoyed the outside amenities including the grill, dining areas and heated pool. Thank you Suki, for an amazing vacation. ..."
Reviewed on Sep 16, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$169 nightly
$186 total
Oct 25 - Oct 26
Total with taxes and fees
8.6/10 Excellent! (311 reviews)
"Checked in early and was told someone would call us when our room was ready. Never heard from anyone. Finally went back to the desk at 4 and it was told it was ready"
Reviewed on Sep 22, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$84 nightly
$93 total
Sep 27 - Sep 28
Total with taxes and fees
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
Frequently asked questions
How much does a Windham vacation package cost?
You can pick up a vacation package to this destination from $867 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
- Hotels near Magic Mountain Ski Resort
- Windham Hotels
- South Londonderry Hotels
- Chalets in Londonderry
- Pet-Friendly Hotels in Londonderry
- Hotels near Jamaica State Park
- Hotels near Bromley Mountain Ski Resort
- Motels in Londonderry
- Grafton Hotels
- Motels in Windham
- Woodstock Hotels
- Cabin Rentals in Grafton
- Pet-Friendly Hotels in Jamaica
- Stratton Hotels
- Hotels near Stratton Mountain Resort
- Vacation Homes in Londonderry
- Cheap Hotels in Londonderry
- Hotels with Kitchenettes in Londonderry
- Best Western Hotels in Londonderry
- Hotels with an Outdoor Pool in Londonderry
- West Townshend Hotels
- Jamaica Hotels
- Resorts & Hotels with Spas in Londonderry
- Hotels with a Pool in Londonderry
- Ski Hotels in Windham
- Weston Hotels
- Rv Parks in Londonderry
- Resorts & Hotels with Spas in Jamaica
- Hotels with Bars in Londonderry
- Pet-Friendly Hotels in Grafton
- Londonderry Hotels
- Cabin Rentals in Jamaica
- Luxury Hotels in Londonderry
- Ludlow Hotels
- Killington Hotels
- Springfield Hotels
- Chester Hotels
- Brattleboro Hotels
- Inns in Londonderry
- Hotels near Okemo Mountain Resort
- Cabin Rentals in Londonderry
- Family Hotels in Londonderry
- Hotels near Lowell Lake State Park
- Hotels near Mount Snow
- Manchester Hotels
- Gay friendly Hotels in Londonderry
- Visit Grafton
- Dorsey Park
- Ball Mountain Dam
- Vermont Museum of Mining and Minerals
- Visit Londonderry
- Viking Nordic Center
- Tamarack Ski Lift
- Visit Weston
- Killington Resort
- Visit Stratton
- Visit Jamaica
- Visit South Londonderry
- Stratton Golf School
- American Express Ski Lift
- Bonnie's Bundles Dolls
- Magic Mountain Ski Resort
- Vermont Country Store
- Winhall River
- Bromley Mountain Ski Resort
- Okemo Mountain Resort
- Hot Glass Works
- Grafton Vacations
- Visit Windham
- Weston Priory
- Plummer's Sugar House
- Bellows Falls Opera House
- Mount Snow
- Chester Vacations
- Stratton Mountain Summit Gondola
- Jud Hartmann Gallery
- Stratton Vacations
- Ursa Express Ski Lift
- Taylor Farm
- Villager Ski Lift
- Bellows Falls Vacations
- Stratton Mountain Resort
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
