Windham Vacations from $571
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The Latest Windham Vacation Packages
- 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 - (1,004 reviews)"The staff was incredibly kind and welcoming!! It’s an old place but the renovations they are working on make the rooms so comfortable. The bed was extraordinary!! The gentleman at the front was so kind and accommodating!!"Reviewed July 21, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - ALB • Nonstop ALB - LGA • Nonstop$696$571found 1 hour agoper traveler - Silver Bay YMCA Inn and Conference Center
Sep 28 - Oct 4Silver Bay YMCA Inn and Conference Center + Flight
Silver Bay6 nights2.0 star property8.8/10 - Excellent (164 reviews)"Everyone was extremely nice and helpful. I really enjoyed the tour I received from the cart driver (I totaly forgot her name, but I do remember she met her husband there and has been volunteering there for many years) She has a passion for the place and after the tour I could see why. Grounds had everything you would need to make your overnight stay or week long stay memorable and relaxing. I was able to fish off the dock, watch the young adults play home run derby on the ball field and..."Reviewed July 13, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - ALB • Nonstop ALB - LGA • Nonstop$1,000$797found 1 day agoper traveler - The Mountain Inn at Killington
Oct 1 - Oct 4The Mountain Inn at Killington + Flight
Killington3 nights2.5 star property9.2/10 - Wonderful (1,004 reviews)"We enjoyed our stay here, it is a great location to the mountain and the staff (and owner) were friendly and fun to talk with. My only recommendation is to get on the upper floor if you can. We had a family staying above us and we heard every step late into the evening and early the next morning, which unfortunately is something we are used to when staying at ski resort properties around the country. Overall though, it is a nice property and we would stay there again!"Reviewed July 20, 2026Roundtrip • Dallas (DFW) - Rutland (RUT)DAL - ALB • 1 stop ALB - DFW • 1 stop$847$720found 8 hours agoper traveler - Greenbrier Inn
Oct 8 - Oct 11Greenbrier Inn + Flight
Killington3 nights2.0 star property9.4/10 - Exceptional (685 reviews)"The hotel was very nice, quaint and clean. It is in a great location just prior to the entry of the access road. Large room. Small hotel with only about 20 rooms. Breakfast included. I would recommend a stay."Reviewed July 16, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - ALB • Nonstop ALB - LGA • Nonstop$728$647found 1 hour agoper traveler - Lake Bomoseen Lodge
Sep 14 - Sep 17Lake Bomoseen Lodge + Flight
Bomoseen3 nights3.5 star property9.4/10 - Exceptional (956 reviews)"Our stay was lovely , however if you are on the first floor you will hear the person walking above you , the walls are thin. We loved the restaurant it was nice & convent, however our waitress really showed little interest with us and our food took forever to get us. Also , last thing , when you arrive you have no idea where to check in. A suggestion for the main office is to put a sign on the front of the building that says office , we literally wandered for a solid 15min before we had to ask..."Reviewed July 20, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - ALB • Nonstop ALB - LGA • Nonstop$719$642found 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
Sun Lodge, an Ascend Collection Hotel
Sun Lodge, an Ascend Collection Hotel
The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain Resort
Frequently Asked Questions
How much does a Windham vacation package cost?
You can pick up a vacation package to this destination from $571 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.