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The Latest Windham vacation packages
Price found within the past 48 hours. Click for updated prices.

The Vermont Inn
Price was $888, price is now $711 per person
$711
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (410 reviews)
Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗
We would stay here again.
Reviewed on Oct 23, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,309, price is now $1,037 per person
$1,037
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!
Reviewed on Nov 5, 2025

Pointe at Castle Hill Resort
Price was $1,272, price is now $1,032 per person
$1,032
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
8.8/10 Excellent! (901 reviews)
Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options.
Reviewed on Nov 5, 2025

Golden Stage Inn B&B
Price was $1,016, price is now $827 per person
$827
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
10/10 Exceptional! (26 reviews)
If you're looking for a cozy, welcoming, and thoughtfully run bed-and-breakfast, the Golden Stage Inn is a true gem. Julie, Mike, and their sweet dog Maisie have created something special—an atmosphere that feels both homey and quietly luxurious.
Every detail is designed for comfort and delight. The breakfasts are consistently amazing, with fresh, hearty options that start your day off right. Our room was not only beautifully kept but also had its own heat adjustment, which made it easy to stay comfortable no matter the weather. The beds? Exceptionally comfortable. We slept soundly every night thanks to the quiet surroundings and the peaceful energy of the inn.
The amenities go far beyond the basics. There’s free parking, of course, but also a puzzle table, board games, and a living room that feels like the heart of the house—complete with soft seating and a glowing fireplace that makes it the perfect spot to read or unwind. Throughout the day, you’ll find hot apple cider, coffee, tea, and cookie jars filled with fresh-baked cookies that somehow taste like childhood and comfort all at once.
Outside, the charm continues. We loved visiting the chickens and soaking in the views—especially at night. The stargazing here is unmatched. It’s the kind of place where you look up and remember how vast and beautiful the world can be.
We had a wonderful time and can’t recommend the Golden Stage Inn enough. It’s not just a place to stay—it’s a place to feel restored.
Reviewed on Oct 18, 2025
Windham Hotel Deals

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Windham
9.8/10 Exceptional! (54 reviews)
This was our second trip to this gorgeous property, and once again, we had a wonderful time. Our group of moms were able to relax in all areas of the home, including the pool and hot tub, fire pit outside and fireplace inside, and on the beautiful deck by the outdoor kitchen. Everything was clean ...
Reviewed on Oct 6, 2025

Jackson Gore Village
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $254 total per night from Nov 23 to Nov 24
$254 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (823 reviews)
The room overall was nice. There were lots of marks on the walls and baseboards. However everything was pretty clean and the fireplace was a nice touch. Unfortunately due to the time of the year we were on our own for food. I wish they told us this ahead of hour stay. Otherwise it was a nice.stay. ...
Reviewed on Oct 29, 2025

Kimpton Taconic Hotel by IHG
3835 Main St., Manchester, VT
Fully refundable
$194 nightly
The price is $213 total per night from Dec 1 to Dec 2
$213 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (812 reviews)
No continental breakfast ,no microwave or in room coffeemaker. Only water or iced tea at check in , no coffee
Reviewed on Oct 25, 2025
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 |
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- Magic Mountain Ski Resort
- Lowell Lake State Park
- Ball Mountain Dam
- Jamaica State Park
- Stratton Tennis School
- Viking Nordic Center
- Plummer's Sugar House
- Grafton Ponds Outdoor Center
- West River Farmers Market
- The Nature Museum
- Gallery North Star
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- Visit Jamaica
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















