Book Luxury Holiday Rentals in Upper East Side

Award-winning homes from £98

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Home spotlights in Upper East Side

Urban Sophistication

Urban Sophistication

  • 2 guests

  • 1 bedrooms

Lenox Hill, Manhattan

Nestled in the Upper East Side, this cosy apartment is an ideal base for tourists and business travellers alike – and for those in the city for work, the desk is just the ticket for catching up on emails outside the office. The bedroom is a bit of a squeeze, but it has everything you need for a comfortable night’s sleep.

Life on Lennox

Life on Lennox

  • 8 guests

  • 3 bedrooms

Lenox Hill, Manhattan

Sample life on the Upper East Side at this pad between Lennox Hill and Central Park. Start your day with a run, or take a class at Equinox opposite your apartment, then return home for coffee on the communal rooftop terrace.

Walk In The Park

Walk In The Park

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

On the edge of the Upper East Side, this duplex apartment puts you a ten-minute walk from Central Park. Grab a New York style bagel to get set for a day of excitement, then hire a bike to tour Central Park, before taking a break at one of the lakes.

Dreams on the Upper East Side

Dreams on the Upper East Side

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

Tucked away in the Upper East Side, this cosy apartment lends itself well to a big city stay. Space is limited, but for a work trip or a weekend getaway it's got a great location, and you can even bring a furry friend for a fee.


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

The Tourist

The Tourist

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

Manhattan Heart

Manhattan Heart

  • 4 guests

  • 2 bedrooms

Upper East Side, Manhattan

The Quartet

The Quartet

  • 12 guests

  • 4 bedrooms

Lenox Hill, Manhattan

Penderyn

Penderyn

  • 2 guests

  • 1 bedrooms

Yorkville, Manhattan

A Weekend In The City

A Weekend In The City

  • 2 guests

  • 1 bedrooms

Upper East Side, Manhattan

The Conga

The Conga

  • 2 guests

  • 1 bedrooms

Lenox Hill, Manhattan

New York, New York

New York, New York

  • 2 guests

  • 1 bedrooms

Upper East Side, Manhattan

With a View

With a View

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

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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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