Windham Vacations from $540
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The Latest Windham Vacation Packages
- Bentley House Bed and Breakfast
Sep 11 - Sep 14Bentley House Bed and Breakfast + Flight
Poultney3 nights2.0 star property10/10 - Exceptional (2 reviews)"Great place, friendly owners. I will be coming back."Reviewed July 11, 2026Roundtrip • Little Rock (LIT) - Rutland (RUT)LIT - BTV • 1 stop BTV - LIT • 1 stop$593$540found 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 - (1,004 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 day agoper traveler - The Mountain Inn at Killington
Sep 11 - Sep 14The Mountain Inn at Killington + Flight
Killington3 nights2.5 star property9.2/10 - Wonderful (1,006 reviews)"This property is liking being home. Everyone was very helpful and welcoming. I needed to call the desk twice for something and they were at my room with what I needed in minutes. The one thing I would let others know is it is an older building so no elevator. It was a bit of a struggle for this 68 year old to lug my bags up three flights of steps especially since I was exhausted from my seven hour drive to get here from Pennsylvania. E still very much enjoyed our stay and the morning continental..."Reviewed July 23, 2026Roundtrip • Little Rock (LIT) - Rutland (RUT)LIT - BTV • 1 stop BTV - LIT • 1 stop$884$766found 1 day agoper traveler - The Quechee Inn at Marshland Farm
Sep 7 - Sep 11The Quechee Inn at Marshland Farm + Flight
Quechee4 nights3.0 star property9.0/10 - Wonderful (1,001 reviews)"Very nice place to stay, giving a farm/country feel. The staff was friendly and very helpful. The restaurant and food was outstanding!"Reviewed July 22, 2026Roundtrip • New York (NYC) - Rutland (RUT)JFK - LEB • 1 stop LEB - JFK • 1 stop$829$729found 17 hours agoper traveler - HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Sep 4 - Sep 7HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles! + Flight
Bolton Landing3 nights3.0 star property9.8/10 - 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 January 18, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - ALB • Nonstop ALB - LGA • Nonstop
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
Frequently Asked Questions
How much does a Windham vacation package cost?
You can pick up a vacation package to this destination from $540 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.