Book Luxury Winter Rentals in Upper West Side

We selected the 690 homes worth renting in this location

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Home spotlights in Upper West Side

Manhattan Medley

Manhattan Medley

  • 4 guests

  • 2 bedrooms

Upper West Side, Manhattan

Immerse yourself in the excitement of Manhattan from this sleek apartment on the Upper West Side. You'll find Central Park, the American Museum of Natural History, and Broadway within easy walking distance.

NYC Soul

NYC Soul

  • 2 guests

  • 1 bedrooms

Upper West Side, Manhattan

This cosy home is located in the heart of the Upper West Side, just a short walk from Central Park and the Hudson River. As you’d expect from a studio, space is limited here, but the location and on-site amenities – which include a gym – more than make up for the smaller space.

New York Spirit

New York Spirit

  • 4 guests

  • 2 bedrooms

Upper West Side, Manhattan

Nestled in the heart of the Upper West Side, this contemporary apartment is an ideal base whether you’re in the city on business or pleasure. The desk in the main bedroom makes remote working a breeze, while the on-site gym ensures you never need to miss a workout.

The Miniature Mint

The Miniature Mint

  • 2 guests

  • 0 bedrooms

Upper West Side, Manhattan

Tucked away in Manhattan's Upper West Side, this studio apartment makes a cosy home base for couples, solo adventurers, and professionals. We love the location, with Riverside Park and the Hudson River just steps away.


We selected the top 3% holiday homes in Upper West Side Vacation Rentals for Winter

Explore the 690 most perfect homes in our collection

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Most popular homes in Upper West Side

Blue Water Lily

Blue Water Lily

  • 3 guests

  • 1 bedrooms

Central Park West Historic District, Manhattan

Central Perk

Central Perk

  • 4 guests

  • 1 bedrooms

Manhattan Valley, Manhattan

A Gentle Touch

A Gentle Touch

  • 3 guests

  • 1 bedrooms

Upper West Side, Manhattan

Joan of Arch

Joan of Arch

  • 7 guests

  • 4 bedrooms

Central Park West Historic District, Manhattan

Red Tomato

Red Tomato

  • 3 guests

  • 1 bedrooms

Central Park West Historic District, Manhattan

Infrared

Infrared

  • 3 guests

  • 1 bedrooms

Central Park West Historic District, Manhattan

Timberlake

Timberlake

  • 4 guests

  • 2 bedrooms

Central Park West Historic District, Manhattan

The Glow Lamp

The Glow Lamp

  • 3 guests

  • 1 bedrooms

Central Park West Historic District, Manhattan

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Check upcoming rates & availability for Upper West Side Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Upper West Side. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Upper West Side. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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