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

5 Stars Hotels in Windham, New York from CA $265

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Check availability on Windham 5 Star Hotels

Tonight
Oct 12 - Oct 13
Tomorrow
Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 modern house with a sloped roof, large windows, and a well-maintained lawn.
A modern house with a large garage and a vintage camper parked in the driveway.
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.

1. AutoCamp Catskills

AutoCamp Catskills
Saugerties
United States
Raquel
CA $187
CA $265 total
includes taxes & fees
Nov 2 - Nov 3
AutoCamp Catskills
A rustic interior with a stone fireplace, wooden beams, and a chandelier.
A rustic cabin interior with a large bed, a clawfoot bathtub, a leather sofa, and a wooden coffee table.
A table set for two with a view of a lush green landscape and hills in the background.
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
CA $271
CA $303 total
includes taxes & fees
Nov 2 - Nov 3
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
CA $466
CA $577 total
Oct 20 - Oct 21
includes taxes & 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
CA $348
CA $376 total
Nov 9 - Nov 10
includes taxes & fees
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

AutoCamp Catskills

AutoCamp Catskills

8/10 Good
"Our stay was great , we really enjoyed the clubhouse the boardgames, a small hike on the property and the airstream was nicely equipped with outside grill, smart tv, and very nice outdoor space. Cleaning wise it was okay, we found hair in the shower drain, futon cover felt unwashed and I wish they had coffee in the clubhouse throughout the day. Would definitely recommend it!"
Mehwish 2-night trip
Posted 2 days ago
AutoCamp Catskills
Urban Cowboy Lodge

Urban Cowboy Lodge

8/10 Good
"Awesome to visit , relax, and enjoy the surroundings. The vibes were sooooo chill, the staff were so cool. But they had 1 big flaw, watch out for the hidden fees, check your bill and invoices before check. They add additional fees if you charge anything to your room for purchases which is crazy. Any charge to your room will be given a servicing fee. If you order breakfast, and pick it up yourself but charge it to your room, you get a fee. If you have dinner or drinks or lunch, and charge it to your room, there’s an extra fee.!!!! So bring cash or pay your bill up front… they use a system called Toast for their credit transactions, and they charge you the convenience / service fee for this system which can be as much as $40 per transaction."
Carlos 2-night trip
Posted 6 days ago
Urban Cowboy Lodge

Find out more about Windham

Five Star Hotels in Windham

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Windham so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Windham and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Windham

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Windham

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. This is a great time to find 5-star hotel deals in Windham! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Windham today and settle down in the lap of luxury tomorrow.

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 things like when you want to go and the length of your stay. Our insider tip for scoring the best deal? Use our pricing filters to compare all of the available accommodations for your selected dates.
  • Search for the lowest price per night from CA $376
What makes a hotel 5 stars in Windham?
In Windham, a hotel needs to offer a certain amount of upscale features to earn a 5-star rating. These can include saunas and spas, on-site gyms, gourmet restaurants, premium bedding, complimentary luxury toiletries and more. What also sets 5-star hotels apart is their outstanding standard of service. You can look forward to things like nightly turn-down services, concierge services and in-room massages. Some may also offer thoughtful touches like a welcome gift.
Are there any 5-star all-inclusive resorts in Windham?
Our filter tool is the quickest way to narrow down what you want. Select "5-star" and "All inclusive" to see the most upscale resorts in Windham where your meals, lodging, activities and entertainment are included in the upfront price. At these getaways, your vacation is pure relaxation and indulgence from the moment you step foot in the lobby.

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