Windham Vacations from $705
Book a Hotel + Flight or Car together to unlock savings
The Latest Windham Vacation Packages
- Greenbrier Inn
Sep 10 - Sep 13Greenbrier Inn + Flight
Killington3 nights2.0 star property9.4/10 - Exceptional (685 reviews)"Nice, clean rooms with comfortable beds and plenty of room. The balconies are comfortable and private, sitting outside in the evening to unwind was nice. Breakfast was just right, plenty of choices and hot fresh coffee"Reviewed July 12, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - RUT • 1 stop RUT - LGA • 1 stop$797$705found 1 day agoper traveler - Mountain Green Resort
Oct 8 - Oct 11Mountain Green Resort + Flight
Killington3 nights4.0 star property4.0/10 - (2 reviews)"I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area. "Reviewed January 28, 2026Roundtrip • San Juan (SJU) - Rutland (RUT)SJU - RUT • 1 stop RUT - SJU • 1 stop$1,911$1,541found 9 hours agoper traveler - Chateau Rooms
Aug 28 - Sep 2Chateau Rooms + Flight
Bolton Landing5 nights4.5 star property9.2/10 - Wonderful (72 reviews)"The property is certainly unique, but you have to know certain things before booking. It’s run more like an Air abnb than a hotel. There’s no formal check-in or check-out process. If you arrive before 5 PM the restaurant will be closed and there will be no one to assist you or answer any questions. There are only three rooms total and they’re all located upstairs above the restaurant. If you can’t get your own bags up the outdoor staircase this may not be the place for you. An access code gets..."Reviewed July 12, 2026Roundtrip • New York (EWR) - Rutland (RUT)EWR - ALB • 1 stop ALB - EWR • 1 stop$1,500$1,251found 1 day agoper traveler - Days Inn by Wyndham Rutland/Killington Area
Oct 8 - Oct 11Days Inn by Wyndham Rutland/Killington Area + Flight
Rutland3 nights2.5 star property6.8/10 - (1,002 reviews)"It was clean and quiet. But the breakfast was horrible the coffee was like water and the syrup was well I don’t know what it was? Plus people were standing by the outside door smoking . We saw a girl climb out her window to smoke !"Reviewed July 18, 2026Roundtrip • San Juan (SJU) - Rutland (RUT)SJU - RUT • 1 stop RUT - SJU • 1 stop$1,019$877found 9 hours agoper traveler - The Mountain Inn at Killington
Sep 10 - Sep 13The Mountain Inn at Killington + Flight
Killington3 nights2.5 star property9.2/10 - Wonderful (1,000 reviews)"Good location. Small pool and no chairs around pool"Reviewed July 16, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - RUT • 1 stop RUT - LGA • 1 stop$938$810found 1 day agoper traveler
Windham Hotel Deals
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
Hampton Inn and Suites Manchester
Hampton Inn and Suites ManchesterFrequently Asked Questions
How much does a Windham vacation package cost?
You can pick up a vacation package to this destination from $705 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.