Luxury rentals in Boys & Girls Club of the Berkshires Ice Rink

The Rye House - Paradise with Pool and Hot Tub

Step into The Rye House, a captivating hillside oasis with 4 bedrooms and 2.5 baths, where every detail is designed to delight and highlight the natural beauty around you. Located just off Copake Lake, this property offers sweeping vistas of the rolling hillside—just 2.5 hrs from NYC! Outdoors, enjoy a pool, built-in hot tub, outdoor dining & lounging by the firepit, and an elevated deck. Inside, well designed interiors invite you to unwind while picture windows frame scenic views. Nearby Town

Hospitality · Location · Pool · Kitchen · Decor · View · Indoor spaces · Amenities · Comfort · Family · Accuracy · Hot tub · Nearby · Cleanliness · Long stay · Getting around · Condition · Outdoor spaces · Value

Mountain estate, indoor sauna & cold plunge

Sunset Falls Estate, the Berkshires 167 private acres — home at 1,400 ft Fifty miles of west-facing ridgeline, vivid gold and red in October Indoor cedar spa: hotrock & infrared sauna, cold plunge, steam room Deck with hot tub, lounging & dining Five ensuite bedrooms + the Bunk Room — sleeps 12 Two wood-burning fireplaces, heated floors throughout Chef's kitchen and Tavern Room Two fire pits, private marked trails Near Great Barrington, Stockbridge, and skiing Dedicated concierge every stay

Hospitality · Location · Amenities · View

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

Hospitality · Indoor spaces · Cleanliness · Location · Comfort · Family · Hot tub · Nearby · Accuracy · Decor · Outdoor spaces · Getting around · Amenities · Skiing · Bathroom · Kitchen · Condition · View · Hiking · Quiet · Sleep quality · Check-in · Grill · Layout · Heating · Parking · Walkability

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.

Hospitality · Indoor spaces · Family · Location · Comfort · Cleanliness · Hot tub · Outdoor spaces · Kitchen · Skiing · View · Grill · Nearby · Amenities · Decor · Accuracy · Hiking · Sleep quality · TV · Layout · Bathroom · Getting around · Backyard · Condition · Quiet · Wifi · Parking · Laundry · Walkability · River · Check-in

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.

Amenities · Hospitality · Cleanliness · Family · Indoor spaces · Pool · Kitchen · Comfort · Hot tub · Location · Accuracy · Outdoor spaces · Bathroom · Backyard · Sleep quality · Check-in · Hiking · Nearby · Condition · View · Value · Decor · TV · Grill · Heating · Parking · Getting around · River · Access · Checkout

Hillcrest Glasshouse - a minimalist modern retreat

The Hillcrest Glasshouse is a fully renovated peaceful retreat with modern carefully selected furniture featuring a breathtaking view over the Hudson River with a fully equipped kitchen, outdoor fire pit, outdoor grill, indoor fireplace, AC, Sonos sound system, Netflix, Amazon Prime, Cable and excellent Wifi to satisfy all leisure and home office activities. This beautiful getaway is only 70 miles away from midtown NYC and close to many of the Hudson Valley's most visited destinations.

Hospitality · View · Decor · Indoor spaces · Comfort · Location · Nearby · Cleanliness · Kitchen · Hot tub · Accuracy · Amenities · Sleep quality · Family · Check-in · Getting around · Backyard · TV · Outdoor spaces · Bathroom · Quiet · Condition · Checkout · Grill · Hiking · Heating · Wifi · Value · Layout · Laundry · Walkability · Breakfast · River · Access · Air conditioning

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 ✔

Hospitality · Indoor spaces · Family · Comfort · Kitchen · Cleanliness · Outdoor spaces · View · Hot tub · Condition · Amenities · Decor · Bathroom · Sleep quality · Check-in · Accuracy · Location · Layout · Backyard · Skiing · Grill · Hiking · Quiet · Getting around · TV · Pets · Access · Checkout · Shared spaces · Value · Air conditioning

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.

Hospitality · Indoor spaces · Kitchen · Family · Comfort · Cleanliness · Decor · Location · Bathroom · Outdoor spaces · Amenities · Accuracy · Sleep quality · Skiing · Layout · Nearby · Condition · TV · Pets · Getting around · Backyard · Check-in · Hiking · Air conditioning · Grill · Quiet · Heating · Parking · View · Noise · Access · Checkout · Shared spaces · Value

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. Designed by ICDT Studio 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.

Hospitality · Decor · Indoor spaces · Comfort · Family · Cleanliness · Accuracy · Layout · Bathroom · Outdoor spaces · Access · Sleep quality · Kitchen · Quiet · Laundry · Amenities

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.

Hospitality · View · Location · Cleanliness · Pool · Decor · Kitchen · Comfort · Indoor spaces · Hot tub · Amenities · Family · Sleep quality · Accuracy · Check-in · Outdoor spaces · Bathroom · Pets · Quiet · Getting around · Condition · Access · TV · Grill · Layout · Nearby · Noise · Checkout · Value · Air conditioning

Modern retreat, Catskill views from Pool & Hot Tub

The House on Slate Hill Road - a private 32-acre retreat with sweeping Catskills views, built for luxury group getaways, wellness weekends & milestone birthdays. Architect-designed with floor-to-ceiling windows, infinity pool (May–Nov) & year-round 7-person saltwater hot tub. Sleeps up to 14. 20 min from Hudson, 5 min to Chatham, ~2.5 hrs from NYC. Adults only. New this September: a multipurpose court for tennis, basketball & pickleball.

Hospitality · View · Amenities · Pool · Indoor spaces · Hot tub · Comfort · Family · Decor · Accuracy · Kitchen · Outdoor spaces · Hiking · Cleanliness · Nearby · Location · Sleep quality · TV · Grill · Check-in

Whimsy Woods - 14 Acre Millbrook Estate with Pool

Whimsy Woods, where contemporary design meets country escape, is a private getaway just minutes from the village of Millbrook. Approaching the property, you’ll feel the rich equestrian history of this historic hamlet, with paddocks and stables, sprawling meadows, and lush lawns. Through the wooden gate, find this uber-private 14-acre estate. The landscape features a mixture of manicured lawns and mature woodlands with walking trails.

Family · Pool · Hospitality · Outdoor spaces · Location · Indoor spaces · Cleanliness · Decor · Long stay · Getting around · Pets · Kitchen · Grill · Hiking · Quiet · Nearby · Amenities