Book Luxury Holiday Rentals in Upper West Side

Award-winning homes from £98

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Age 13+

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Age 1 to 12

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Home spotlights in Upper West Side

Manhattan Heart

Manhattan Heart

  • 4 guests

  • 2 bedrooms

Upper East Side, Manhattan

You’ll find this contemporary apartment in the heart of the Upper East Side – and with easy access to a selection of subway lines, hopping across the city is a breeze. With high-speed wi-fi and a desk in the second bedroom, remote working is easy for those in the city on business.

The New Manhattan

The New Manhattan

  • 6 guests

  • 3 bedrooms

Lenox Hill, Manhattan

This family-size home is only a short walk from Central Park, with many of NYC's other major landmarks within easy reach. Located on the Upper East Side, you'll be just a few steps away from historical buildings, trendy eateries and high-end boutiques.

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.

Central Perk

Central Perk

  • 4 guests

  • 1 bedrooms

Manhattan Valley, Manhattan

Situated in NYC's affluent Upper West Side – known for its stately brownstones, museums and world-famous park – this modern apartment is perfectly set up for a solo traveller or couple looking to explore the Big Apple. Inside, it's a perfectly practical pad with an open-plan living space that allows you to glide seamlessly across the polished wooden floor between the kitchen and seating area.


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

Explore the 688 most perfect homes in our collection

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Most popular homes in Upper West Side

NYC Soul

NYC Soul

  • 2 guests

  • 1 bedrooms

Upper West Side, Manhattan

The Wizards of Central Park

The Wizards of Central Park

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

One Day in New York

One Day in New York

  • 4 guests

  • 1 bedrooms

Hell's Kitchen, Manhattan

Madison Square South

Madison Square South

  • 4 guests

  • 2 bedrooms

West Village, Manhattan

The Modern Times

The Modern Times

  • 10 guests

  • 5 bedrooms

Lenox Hill, Manhattan

A Gentle Touch

A Gentle Touch

  • 3 guests

  • 1 bedrooms

Upper West Side, Manhattan

The Miniature Mint

The Miniature Mint

  • 2 guests

  • 0 bedrooms

Upper West Side, Manhattan

Eastside Elegance

Eastside Elegance

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

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Check upcoming rates & availability for Upper West Side Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Upper West Side. 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 West Side 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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