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Luxury rentals in The Berkshires

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Top-rated luxury vacation rentals in The Berkshires

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

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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, 14 reviews

Luna Cove: Premier Hudson Valley Getaway

JunkoRating, 5 stars2 months ago

We had an amazing time at this house! Upon entering, our jaws dropped—it was absolutely gorgeous! We were in awe of how spacious and beautifully designed it was. The house looked even better in person than in the photos. Everything was spotless, and it had all the amenities we needed for a comfortable stay. We were a group of 12 (6 kids and 6 adults) and felt right at home. The kitchen was fully equipped, which was perfect since we cooked a lot during our stay. The kids absolutely loved the attic—it was such a fun space for them to play. The game room was also a big hit for our whole family! (We had a family air hockey tournament!) The management was so responsive anytime we had questions or concerns, which made our stay even more enjoyable. We truly enjoyed our stay and can’t wait to come back. Highly recommend this place!

An aerial view captures a stylish retreat surrounded by greenery, featuring a spacious swimming pool with sun loungers on the edge. The main house sits prominently, framed by trees and mountains in the background, complemented by a guest house nearby.

Home in Kerhonkson

4.71 out of 5 average rating, 7 reviews

Home Sweet Hudson: A Retreat @ Hudson Woods

MeredithRating, 5 stars5 months ago

A Retreat @ Hudson Woods was just the right place for a ladies' reunion long weekend. The house and property were gorgeous, and the Home Sweet Hudson staff was responsive and proactive. My group loved the decor and laid back luxury vibe of this property and would stay here again in a heartbeat. Other than some very minor annoyances with locks, speakers, water filters, and WiFi, this was one of the best AirBnBs that I've ever stayed in. One draw back; A Retreat @ Hudson Woods felt a little too remote and private. While we wanted an escape, it was a solid 20-45 minute drive on very windy roads to get to decent dining options. We cooked most of our meals on site and would recommend that for other future guests!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for The Berkshires luxury vacation rentals

Free parking on premises

Air conditioning

Other great luxury vacation rentals in The Berkshires

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, 14 reviews

Luna Cove: Premier Hudson Valley Getaway

JunkoRating, 5 stars2 months ago

We had an amazing time at this house! Upon entering, our jaws dropped—it was absolutely gorgeous! We were in awe of how spacious and beautifully designed it was. The house looked even better in person than in the photos. Everything was spotless, and it had all the amenities we needed for a comfortable stay. We were a group of 12 (6 kids and 6 adults) and felt right at home. The kitchen was fully equipped, which was perfect since we cooked a lot during our stay. The kids absolutely loved the attic—it was such a fun space for them to play. The game room was also a big hit for our whole family! (We had a family air hockey tournament!) The management was so responsive anytime we had questions or concerns, which made our stay even more enjoyable. We truly enjoyed our stay and can’t wait to come back. Highly recommend this place!

An aerial view captures a stylish retreat surrounded by greenery, featuring a spacious swimming pool with sun loungers on the edge. The main house sits prominently, framed by trees and mountains in the background, complemented by a guest house nearby.

Home in Kerhonkson

4.71 out of 5 average rating, 7 reviews

Home Sweet Hudson: A Retreat @ Hudson Woods

MeredithRating, 5 stars5 months ago

A Retreat @ Hudson Woods was just the right place for a ladies' reunion long weekend. The house and property were gorgeous, and the Home Sweet Hudson staff was responsive and proactive. My group loved the decor and laid back luxury vibe of this property and would stay here again in a heartbeat. Other than some very minor annoyances with locks, speakers, water filters, and WiFi, this was one of the best AirBnBs that I've ever stayed in. One draw back; A Retreat @ Hudson Woods felt a little too remote and private. While we wanted an escape, it was a solid 20-45 minute drive on very windy roads to get to decent dining options. We cooked most of our meals on site and would recommend that for other future guests!

The spacious property showcases lush greenery and a variety of amenities, including an in-ground pool and a private pickleball court. Surrounding areas are landscaped, providing a serene outdoor setting ideal for relaxation and recreation. The house is set against a backdrop of rolling hills.

4.94 out of 5 average rating, 16 reviews

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

JanetRating, 5 stars6 days ago

A great house for our extended family of all ages. Plenty of space for everyone. Full kitchen. Fabulous outdoor space especially for families with children. So much to do. Would love to be there in the summer too.

The modern retreat is set among trees with a combination of wooden and sleek black exterior. A spacious concrete patio extends in front, with outdoor seating visible. Natural stone paths lead up to the entrance, blending harmoniously with the surrounding forest landscape.

Home in Catskill

4.96 out of 5 average rating, 25 reviews

Escape To The Woods, Light-Filled Modern Home

StavRating, 5 stars1 week ago

Highly recommend this stay! We had an amazing time at this beautiful property. Every detail was thoughtfully considered, the host was wonderful, and the place itself was truly incredible.

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 stars6 months ago

The place was absolutely stunning and so was the experience. Great host, booking experience, and an epic place! Highly recommend!

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