A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Find 5 Star Hotels in Windham, NY from $189

Check availability on Windham 5 Star Hotels

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Windham 5-star hotels

A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.
A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.
A modern house with a large garage and a vintage camper parked in the driveway.
A modern interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.

1. AutoCamp Catskills

AutoCamp Catskills
Saugerties
United States
Raquel
$169 nightly
$189 total
Nov 19 - Nov 20
Total with taxes and fees
AutoCamp Catskills
A rustic interior with a stone fireplace, wooden beams, and a chandelier.
A table set for two with a view of a lush green landscape and hills in the background.
A rustic cabin interior with a large bed, a clawfoot bathtub, a leather sofa, and a wooden coffee table.
A rustic interior with wooden beams, a chandelier, and a seating area with tables and chairs.

2. Urban Cowboy Lodge

Urban Cowboy Lodge
Big Indian
United States
Karcynn
$190 nightly
$213 total
Nov 2 - Nov 3
Total with taxes and fees
Urban Cowboy Lodge
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Windham.
Woodstock Way Hotel

Woodstock Way Hotel

10 Waterfall Way Woodstock NY
$409 nightly
$454 total
Nov 2 - Nov 3
Total with taxes and fees
Woodstock Way Hotel
Scribner's Catskill Lodge, A Member Of Design Hotels

Scribner's Catskill Lodge, A Member Of Design Hotels

13 Scribner Hollow Road Hunter NY
Get ratesScribner's Catskill Lodge, A Member Of Design Hotels
Hotel Mountain Brook

Hotel Mountain Brook

57 Route 23c Tannersville NY
$224 nightly
$242 total
Nov 16 - Nov 17
Total with taxes and fees
9.8/10 Exceptional! (609 reviews)
Hotel Mountain Brook
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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.

Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

See all hotels in Windham
Two skiers on a snowy slope with a valley and mountains in the background.

Top Windham Hotel Reviews

Urban Cowboy Lodge

Urban Cowboy Lodge

10/10 Excellent
"Amazing"
Steve 2-night trip
Posted 2 days ago
Urban Cowboy Lodge

Find out more about Windham

Ready for an incredible adventure? Add even more luxury on your next trip to Windham by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Windham so popular in the last year. There's no reason to delay a getaway to Windham any longer. Furthermore, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. Our 5-star hotels in Windham are the perfect places to relax in during your next getaway. Don't wait any longer!

5-Star Hotels in Windham

Don't be afraid to request the best service from your hotel, along with pristine rooms. Excellent customer care, luxurious bedding, and rejuvenating spa offerings are all on offer. You're sure to find exactly the accommodation you need. We should also mention, the hotels in this area receive fantastic marks for customer satisfaction, so you know you'll be well cared for during your getaway. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A deep-tissue massage to help your cares fall away? Comfortable beds, piping hot coffees, and even spectacular views...these hotels will leave you amazed. Want to see for yourself? Plenty of visitors recommend this location.

Yearning for experiences outside your hotel room? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Windham are waiting for you to rest up after an exciting day.

Your Getaway Starts Today

The results are in, and Windham 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. It's time to indulge yourself -- Expedia can help you land a great deal on accommodation. Opt for one of our Windham 5-star hotels today and relax in total tranquility at your convenience.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Windham?
How much you pay for a 5-star hotel in Windham depends on factors such as when you plan to go and the length of your trip. Our insider tip for bagging the best deal? Use our pricing filters to compare all of the available hotels for your chosen dates.
  • Search for the lowest price per night from $242
What makes a hotel 5 stars in Windham?
From gourmet restaurants and all-day fitness centers to pools and premium bedding, the 5-star experience in Windham is all about luxury and relaxation. But it requires more than just top-notch perks to receive a 5-star rating. Accommodations must also deliver extraordinary guest-focused services like beauty treatments, on-site laundry and 24-hour concierge services.
Are there any 5-star all-inclusive resorts in Windham?
Our filters are the best way to find exactly what you're looking for. Select "5-star" and "All inclusive" to see the most upscale resorts in Windham where your accommodations, meals, activities and entertainment are included in the upfront price. At these retreats, your trip is pure extravagance from the moment you enter the lobby.

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