Luxury rentals in Western Massachusetts

Find and book unique accommodations on Airbnb

Top-rated luxury vacation rentals in Western Massachusetts

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

%{current} / %{total}1 / 1

Luxe

Home in Craryville

5 out of 5 average rating, 11 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

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 Chatham

5 out of 5 average rating, 27 reviews

Modern retreat, Catskill views from Pool & Hot Tub

Enjoy stunning views of the Catskills! Set on 32 acres, located close to the Taconic Pkwy & only 5 mins from Chatham. 7 person salt water hot tub open year round + infinity edge pool with large hot tub open May to Nov. The house has a 14 person dining room table and can accommodate up to 14 people with: 4 bedrooms; 1 study with a convertible couch; & 2 Murphy beds. Additional fee above 8 guests. ADULTS ONLY. Inquire if dates aren't available!

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.

Luxe

Home in Austerlitz

5 out of 5 average rating, 4 reviews

Pond, Gym & Movie Theater • Optional Guest House

★ Sunny Pond by AvantStay ★ - Stunning, secluded estate located on a private swimming pond - Fully equipped gym with a Peloton - Movie room and playroom stocked with toys and games - Gourmet chef’s kitchen with top-of-the-line appliances - 7 bedrooms, three living areas, two dining areas, and a home office - Expansive yard boasting serene forest views - 2 BR guest house available for an additional fee