Luxury rentals in Greene County

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Top-rated luxury holiday rentals in Greene County

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Luxe

The spacious living area features high, vaulted ceilings with natural wood beams and an elegant antler chandelier. Large windows allow abundant natural light, offering views of the surrounding greenery. A central coffee table is complemented by a cozy sofa and several armchairs, creating an inviting atmosphere.

Cabin in Windham

5.0 out of 5 average rating, 45 reviews

NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym

Immerse yourself in luxury at Timber Trail Lodge, an opulent 5-bedroom, 4 full bathroom estate nestled in Windham’s premier location. This expansive 4,000 ft² home offers the ultimate mountain escape, high-end amenities such as a modern spa, chef’s kitchen, Sonos, and an outdoor fire pit, perfect for entertaining. Adventure seekers can enjoy a private zip-line and proximity to Windham Mountain 8 minutes away. Timber Trail Lodge combines modern comfort, outdoor fun, and serene Mountain View’s

HospitalityIndoor spacesCleanlinessLocationComfortFamilyHot tubNearbyAccuracyDecorOutdoor spacesGetting aroundAmenitiesSkiingBathroomKitchenConditionViewHikingQuietSleep qualityCheck-inGrillLayoutHeatingParkingWalkability

Luxe

Home in Hunter

5.0 out of 5 average rating, 53 reviews

Casa Catskills: Luxury, Modern 9 Acre Escape

Escape to Casa Catskills, a modern, luxury mountain retreat on 9 private acres just 10 mins from Hunter & Windham Ski Resorts. The home’s amenities include a theater room, hot tub, sauna, pool table, multiple fireplaces, fully equipped kitchen with PFAS-free cookware and dedicated office space with beautiful mountain views. Enjoy 6 serene bedrooms (3 kings, 2 queens, 2 twins) and 5 spa-like bathrooms with radiant floors. Perfect for a wellness reset or city getaway. VIP services available.

HospitalityIndoor spacesFamilyLocationComfortCleanlinessOutdoor spacesHot tubKitchenSkiingViewGrillNearbyAmenitiesDecorHikingSleep qualityTVAccuracyLayoutBathroomGetting aroundConditionQuietWifiParkingLaundryWalkabilityRiverBack gardenCheck-in

Luxe

Home in South Cairo

4.96 out of 5 average rating, 45 reviews

Luna Cove: Premier Hudson Valley Getaway

Luna Cove is conveniently located between two iconic towns; Hudson, NY and Woodstock, NY. The estate offers many amenities for your leisure. You can enjoy access to a natural swimming hole, the hot tub, pickleball court, and barrel sauna! This property also offers a game room and a theater room along with a wellness spa. In addition to the main section of the home, there is a private wing with a separate external entrance featuring two bedrooms, a full bathroom, and its own kitchen area.

AmenitiesHospitalityCleanlinessFamilyIndoor spacesPoolKitchenComfortHot tubLocationAccuracyOutdoor spacesBathroomBack gardenSleep qualityCheck-inHikingNearbyConditionViewValueDecorTVGrillHeatingParkingGetting aroundRiverAccessCheckout

Luxe

Home in Jewett

4.96 out of 5 average rating, 77 reviews

8BR Luxury Retreat, Hot Tub, Gym & Games

Welcome to Maplewood Manor, 8-bedroom retreat on 44 acres, less than 8 min to Hunter & Windham Ski Mountains. Ideal for ski trips, family getaways and outdoor adventures. This 7000 sq ft estate blends modern amenities with rustic charm. Featuring a home gym, hot tub, ping pong, mini pool table, volleyball, and movie room. ✔ 4 Comfy King + 6 Queen Beds ✔ Endless Mountain Views with Deck, Pond + Hot Tub ✔ Fire Pit, Outdoor Dining, + BBQ ✔ 7 Smart TVs + 4K Projector ✔ 600 Mbps Wi-Fi ✔

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Luxe

Home in Jewett

5.0 out of 5 average rating, 89 reviews

Modern Luxury in the Catskills! New 7 Bedroom Home

At only a 2.5 hour drive from New York City, this stunning and modern 7 bedroom, 5 bathroom 4,000 square foot house just underwent a 2 year gut-renovation to become the perfect weekend retreat for anyone looking to experience the countless activities the Catskills has to offer! Although very private on 3 acres, the house is just minutes away from skiing, snowboarding, hiking, lakes, swimming holes, mountain biking, shopping, and a 40 minute drive to Woodstock and Hudson.

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Luxe

A large outdoor space features a modern fire pit surrounded by four mesh chairs. The adjacent lap pool reflects the colorful sunset sky and is framed by a sleek glass house with expansive sliding doors, creating a seamless connection to the natural surroundings.

Home in Hudson

4.81 out of 5 average rating, 43 reviews

Hudson Ridge | Hot Tub, Fire Pit & Fireplace

A stunning glass house with a breathtaking pool extending toward the Catskills. Set on 25 secluded acres in Hudson Valley, this architectural gem—featured in The New York Times—draws inspiration from Pierre Koenig’s Stahl House. Floor-to-ceiling glass surrounds two serene bedrooms, opening to a seasonal pool and year-round hot tub. Enjoy fast WiFi, two workstations, and total tranquility in this unique escape blending East Coast nature with West Coast charm.

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Luxe

Home in Town of Gilboa

5.0 out of 5 average rating, 18 reviews

Potter Mountain House: New Catskills Luxury Estate

Click: "Show more" to read full description. Stay in a newly restored 19th-century Greek Revival church in the high peaks of the Northern Catskills. Just 20 min to skiing at Windham Mountain! Potter Mountain House offers panoramic views from nearly every room with soaring ceilings, original wood beams, gas fireplace, chefs kitchen, office, a walk-in wine room and library within the steeple and four serene bedrooms and spa-like bathrooms.

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Luxe

Home in Saugerties

5.0 out of 5 average rating, 20 reviews

The Creek Lodge

Welcome to The Creek Lodge, a peaceful retreat nestled in the heart of the Catskill Mountains. Tucked away on 3 private wooded acres with 2 babbling creeks running through the property, this modern, fully-equipped home offers the perfect blend of comfort, luxury, and nature, for a serene upstate getaway. Whether you're here to relax, hike, or explore the charming local towns, you'll find everything you need for an unforgettable stay.

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Luxe

Cabin in Windham

4.86 out of 5 average rating, 81 reviews

Lux Mansion Windham: Hot Tub, Sauna, Mountain View

❆ Experience the ultimate retreat at Ulula Eco Resort, where luxury meets nature in the scenic Catskills. This 4770 sq ft chalet, made entirely of eco wood, features plush king-sized beds and a gourmet kitchen. Enjoy breathtaking views and top-notch amenities like a ground-level hot tub, sauna and cozy fire pit. Perfectly situated near Windham Ski Resort, it's the ideal base for skiing or serene mountain escapades.

HospitalityIndoor spacesCleanlinessLocationAmenitiesAccuracyComfortFamilyHot tubOutdoor spacesViewKitchenConditionCheck-inNearbyDecorSkiingGrillHikingLayoutBathroomSleep qualityCheckoutLaundryWalkabilityAccessTVPetsQuietGetting aroundBack gardenEV charging

Luxe

Home in Hunter

5.0 out of 5 average rating, 43 reviews

Riverside Hot Tub, Cedar Sauna & Arcade Games

Riverside Hunter home with 6-person hot tub overlooking the water, Finnish cedar sauna, arcade game room, and wood-burning stove—1 minute from Hunter Mountain Resort entrance. Main Street restaurants and Fellows café are walkable, hiking trails under 5 minutes away. EV charger, fire pit, and waterfront setting with mountain views. Built for families and groups who want entertainment on-site.

HospitalityIndoor spacesCleanlinessFamilyLocationHot tubComfortKitchenWalkabilityViewNearbyAmenitiesAccuracyDecorTVBathroomSkiingGetting aroundRiverBack gardenHikingConditionOutdoor spacesGrillSleep qualityLayoutLong stayNoise