Luxury rentals in The Berkshires

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Popular amenities for The Berkshires luxury vacation rentals

Other great luxury vacation rentals in The Berkshires

Luxe
A large, modern estate is displayed from a frontal viewpoint, featuring a mix of black and white siding. Solar panels are visible on the roof. Neatly trimmed shrubs line the property, and a wide porch extends across the front, providing ample outdoor space.
Home in South Cairo
5 out of 5 average rating, 17 reviews

Luna Cove: Premier Hudson Valley Getaway

MalvinaRating, 5 stars1 month ago
The house was incredibly clean and tidy, and very welcoming! The table in the main area was perfect for our dinner of 11 ladies where we could comfortably gather to celebrate, and the upstairs media room was perfect for our karaoke night! This was a beautiful house and space, and we had a wonderful stay!
Luxe
An aerial view captures the modern retreat nestled among lush trees. Large windows reflect natural light, and a spacious deck is furnished with chairs. Surrounding green grass and flourishing gardens enhance the peaceful atmosphere, inviting guests to enjoy the serene outdoor setting.
Home in Kerhonkson
4.75 out of 5 average rating, 8 reviews

Home Sweet Hudson: A Retreat @ Hudson Woods

AndyRating, 5 stars3 weeks ago
Excellent stay! The house/property exceeding expectations - the pool house, pool, and living quarters were in great condition and my group really enjoyed the amenities. The house is in a lovely area to just unwind, enjoy the outdoors, and visit some of the local shops/restaurants in the area. Thank you! Would come back again.
Luxe
An aerial view captures the expansive outdoor space, featuring a heated swimming pool, a multi-sport court with a vibrant blue and green surface, and a fire pit area surrounded by greenery. The charming home is nestled amidst lush trees and manicured gardens.
Home in Hurley
4.95 out of 5 average rating, 21 reviews

Family Manor Sleeps 18 w Pickleball, Pool, HT, FP

CathyRating, 5 stars2 weeks ago
We had a group of 8 adults and 8 kids ranging from 1-10yo, and there was plenty of space for everything we needed to do! All were entertained and enjoyed the outside and inside spaces, especially the pickleball/basketball area, hot tub, pool (although very cold in May), foosball. There were a few things that didn't work but nothing major and hosts were very responsive with help. Very clean even for a pet-friendly place. Would definitely recommend for large groups with kids of pretty much any age. The hosts also provide a online guide that contains lots of tips and local recommendations, very helpful. Forsyth Nature Center (and playground) and Kingston Farmers Market (both free) were highlights for us.
Luxe
An infinity pool is surrounded by well-maintained grassy areas and features a hot tub that complements the serene landscape. Several lounge chairs are positioned along the edge of the pool, offering a relaxing vantage point of the surrounding trees and meadows.
Place to stay in Hyde Park

Historic Vanderbilt Estate Carriage House

BrittanyRating, 5 stars8 months ago
Absolutely amazing stay! This home is everything we hoped for - extremely clean, beautiful decor and such a peaceful property. The owners truly thought of everything. The property is so beautiful - we did not want to leave. We will definitely be back!
Luxe
A modern living room features floor-to-ceiling windows offering a sunset view over rolling hills. Comfortable seating arrangements are present, alongside a geometric light fixture. Natural stone accents complement the space, enhancing the connection with the surrounding landscape.
Home in New Marlborough
5 out of 5 average rating, 3 reviews

Sunset Falls: A Berkshire Mountain Luxury Retreat

MichaelRating, 5 stars7 months ago
The place was absolutely stunning and so was the experience. Great host, booking experience, and an epic place! Highly recommend!
Luxe
A modern dining area is highlighted by a long wooden table surrounded by eight upholstered chairs. The space features a cozy fireplace with a decorative stone wall and a unique overhead light fixture. Large windows provide a view of the outdoors, enhancing the inviting ambiance.
Home in Catskill
4.96 out of 5 average rating, 28 reviews

Secluded modern home with private creek

ScottRating, 5 stars2 weeks ago
My fiancé and I had a delightful stay. The location is beautiful, perfect for anyone looking for a private getaway. Very beautiful open kitchen and living areas. Host is proactive and responds very quickly. Check in & check out very smooth and straight forward.
Luxe
Place to stay in Lenox

The Kemble Berkshires

Destinations to explore