Luxury rentals in Western Massachusetts

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Top-rated luxury vacation rentals in Western Massachusetts

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Luxe

A modern house with a Scandinavian design is nestled among tall grass and wildflowers. Large windows provide views of the surrounding landscape, while a sloped roof adds to the contemporary aesthetic. The structure is framed by lush greenery under a partly cloudy sky.

Home in Taghkanic

Taghkanic House: Modern Oasis | Designer | Privacy

Taghkanic House is a modern Scandinavian inspired 5 bed, 3.5 bath retreat just 2 hours from NYC & minutes away from Taghkanic Lake for swimming & hiking. Set on 16 acres with sweeping views of the Catskills & designed with sustainability in mind, this eco-friendly home boasts rooftop solar panels, an EV charger, outdoor shower & large windows throughout that fill the space with natural light. Nearby towns: Hudson (20mins), Copake (20mins), Hillsdale (20mins), Catamount (30mins), Windham (45mins

Luxe

A spacious elevated deck offers two modern white lounge chairs centered around a small round table. The area is framed by glass doors, providing unobstructed views of the rolling green hillside under a partly cloudy sky.

Home in Craryville

5 out of 5 average rating, 9 reviews

The Rye House: Paradise w/Pool+Hot Tub

Step into The Rye House, a captivating hillside oasis with 3 bedrooms, a nursery, 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.

Luxe

Home in Hudson

Heated Pool! Sauna! Gym! Stunning Retreat + Views!

Skyline Ridge is a modern 4 bed, 4.5 bath getaway with breathtaking views, just under 3 hours from NYC. Chic and comfortable, it showcases sweeping vistas of the Hudson River and Catskill Mountains. Enjoy a prime location minutes from Hudson, plus a heated pool, hot tub, sauna, gym, fireplace, firepit, grill and laptop friendly workspaces. Nearby towns: Hudson (5mins), Catskill (10mins), Athens (10mins), Germantown (10mins), Saugerties (25mins), Woodstock (35mins)

Luxe

A modern home with a curving roof features floor-to-ceiling windows that reflect the soft colors of sunset. The exterior combines stone and wood elements, surrounded by lush greenery. A pathway leads to the main entrance, integrating outdoor and indoor spaces.

Home in New Marlborough

5 out of 5 average rating, 3 reviews

Sunset Falls: A Berkshire Mountain Luxury Retreat

Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. Open-concept living areas, floor-to-ceiling windows, and spacious great room. Breathtaking mountain views and full-service luxury amenities. Perfect for family gatherings and romantic getaways, this private oasis provides a serene escape, promising a unique, pampered experience with concierge service, ensuring a stay beyond the typical Airbnb.

Luxe

Home in Austerlitz

5 out of 5 average rating, 3 reviews

Sunny Pond Estate | Private Pond, Gym, Sleeps 20

★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-tier stays. - Stunning, secluded estate located on a private swimming pond - Gourmet chef’s kitchen with top-of-the-line appliances - 9 bedrooms, three living areas, two dining areas, and a home office - Fully equipped gym with a Peloton - Movie room and playroom stocked with toys and games - Expansive yard boasting serene forest views

Luxe

The stately mansion features multiple outdoor seating areas, including comfortable lounge chairs arranged on a stone patio. The venue's iconic architecture is visible in the background, framed by well-maintained greenery and a bright blue sky.

Place to stay in Lenox

The Kemble Berkshires

Located in Lenox, one of Berkshire's most vibrant towns, this Gilded Age mansion is a beautiful event space with sweeping mountain views from the heart of the town. Your large group will appreciate the estate’s generous outdoor entertaining area, games rooms, and chef’s kitchen. In town, you’ll find delightful restaurants, bakeries, and antique shops. Copyright © Luxury Retreats. All rights reserved.