Book Luxury Holiday Rentals in Upper East Side

Award-winning homes from £98

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Home spotlights in Upper East Side

Safe & Sound

Safe & Sound

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

Why compromise a good night's rest when you come to the city that never sleeps? There's no need to in this quiet and calming Upper East Side duplex.

The Art of New York

The Art of New York

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

Situated on 75th Street and 2nd Avenue, this Upper East Side home is an excellent base from which to explore the Big Apple. With cosy interiors, the bedrooms are on the small side – that said, they have everything needed for a comfortable night’s sleep, and one includes a desk, perfect for remote workers.

Maple & Walnut

Maple & Walnut

  • 8 guests

  • 3 bedrooms

Lenox Hill, Manhattan

Located in the heart of Lenox Hill on the Upper East Side, this modern apartment presents an open-concept main living area for guests to relax and socialise between adventures out in New York City. This walk-up apartment also shares a furnished rooftop terrace and lobby area.

Eastside Elegance

Eastside Elegance

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

This New York apartment made it into our collection for its desirable location in the Upper East Side. You’ll have the Guggenheim close by for culture and Madison Avenue for shopping, as well as an array of eateries serving everything from classic New York bagels to Michelin-starred cuisine.


We selected the top 3% holiday homes in Upper East Side Holiday Rentals

Explore the 78 most perfect homes in our collection

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Most popular homes in Upper East Side

Urban Sophistication

Urban Sophistication

  • 2 guests

  • 1 bedrooms

Lenox Hill, Manhattan

Up & Up

Up & Up

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

Eye of the Storm

Eye of the Storm

  • 4 guests

  • 1 bedrooms

Lenox Hill, Manhattan

The Dame

The Dame

  • 4 guests

  • 1 bedrooms

Lenox Hill, Manhattan

Yorkville Chic

Yorkville Chic

  • 2 guests

  • 1 bedrooms

Yorkville, Manhattan

Studio Vision

Studio Vision

  • 2 guests

  • 1 bedrooms

Yorkville, Manhattan

Upper East Side

Upper East Side

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

The Tourist

The Tourist

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

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Check upcoming rates & availability for Upper East Side Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Upper East Side, Manhattan, New York, New York, United States. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Upper East Side, Manhattan, New York, New York, United States has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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