Holiday houses in Upper West Side

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Top-rated holiday rentals in Upper West Side

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

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Top Guest favourite
The living area features a spacious sectional sofa, a wooden coffee table, and decorative shelving units displaying items. A television is mounted on the wall, and natural light filters through the large windows dressed with soft curtains. The layout promotes an inviting atmosphere.
Apartment in Midtown East
4.96 out of 5 average rating, 108 reviews

Spacious Historic Manhattan Residence – Prime Area

Experience the comfort of a spacious one-bedroom brownstone apartment that accommodates up to five guests. Located near Central Park, Times Square, and Fifth Avenue, this spot offers convenience and proximity to New York City’s most iconic attractions. Perfect for short or extended stays, it provides a comfortable home base in Manhattan. The unit is on the second floor of a walk-up with two sets of stairs, which may not suit everyone, but many guests find the space and location well worth it!!

Guest favourite
A spacious bedroom features a comfortable bed with plush pillows. Natural light filters through sheer curtains, illuminating the soft beige walls. A minimalist television is mounted on the wall opposite the bed, and a stylish ottoman adds a touch of texture.
Hotel room in New York
4.73 out of 5 average rating, 256 reviews

Luxury Penthouse Suite near Central Park

The Manhattan Club is the perfect combination of luxury and location in the heart of New York City. Spend time in one of the oversized Penthouse Suites or enjoy your Penthouse Exclusive balcony for great views! (Exclusive to all Penthouse Guests, not private, open seasonally) Incidentals: $500 authorization at Check-in. Must present valid credit card and government ID (21 years of age) Price Includes All Taxes/Fees (There will be no additional tax or daily fees charged during your stay. )

Superhost
A modern studio space features a comfortable seating area with a plush blue sofa and a light-colored armchair beside a circular coffee table. Natural light pours in through large windows, creating an airy atmosphere. In the background, two beds are set against a clean, neutral wall.
Apartment in Upper East Side
4.83 out of 5 average rating, 157 reviews

Luxe Studio with Charming Juliet Balcony

Stay at our BEAUTIFUL studio flat with a charming Juliet balcony located in the Upper East Side! This gorgeous boutique building is nestled near some of the best attractions the city has to offer. With an unbeatable location - minutes away from Central Park, Park Ave, and 5th Ave! Bloomingdale's is a block away, along with many trendy restaurants and shops! Enjoy dinner steps away at delicious restaurants such as Sushi Seki, and grab dessert at the famous Magnolia Bakery on your way home!

Top Guest favourite
A cozy bedroom features a spacious bed adorned with patterned pillows and a decorative blanket. Green curtains frame a window, while a wall-mounted shelf displays artwork and accessories. A small table with a cup stands at the bedside, adding functionality to the inviting space.
Apartment in Manhattan Valley
4.99 out of 5 average rating, 164 reviews

5 bdrm, 2 bath apt on Manhattan’s Upper West Side!

Click my profile to see my reviews! Live like a real New Yorker, right in the thick of it on Manhattan’s Upper West Side, the best neighborhood in the city! Steps from a major subway line, this 4th fl. apt. in an elevator building has everything you need for a home away from home. All the major sites are accessible: Lincoln Center, Columbus Circle, Central Park, Natural History Museum all w/in walking distance. Columbia U. a few blocks north. Come stay and live like a real Manhattanite!.

Guest favourite
The living area features a contemporary brown leather sofa paired with light-colored pillows. A decorative fireplace with a mosaic surround anchors the space. Two round wooden coffee tables are centered on a patterned rug, with a small vase and candles on display.
Loft in Manhattan
4.95 out of 5 average rating, 79 reviews

1 Min to Subway: King Bed, Luxe Airy Space + Patio

Welcome to Vintage Luxe, a stunning 1894 landmark in Sugar Hill restored into a luxurious boutique! This charming unit includes an accent fireplace, bay windows, a king bed, high-speed WiFi, a dedicated workstation, and a fully equipped kitchen. Step outside to your private patio—a rare NYC luxury. With a prime location just 1 minute from the metro and close to Yankee Stadium, this space is perfect for couples, families, or groups seeking a central and elegant stay.

Top Guest favourite
A cozy bedroom features an antique brass bed with soft bedding adjacent to a wall of bookshelves filled with various literature. A decorative mirror reflects the room's warm light, while a vintage-style fireplace complements the eclectic decor. A colorful area rug enriches the floor space.
Guest suite in Washington Heights
4.94 out of 5 average rating, 160 reviews

Elegant Uptown Historic District Garden Suite

Your pied-à-terre on Sugar Hill in the Jumel Terrace Historic District. Formerly a rare bookshop, the garden suite resounds with Harlem Heights' history from the Founding Fathers thru the Founding Brothers to our vibrant now. Think privacy, quiet, autonomy and a garden in bloom. Short walk, one subway stop, to NY/Columbia-Presbyterian. This is a two family house. Fully compliant with NYC short term rental laws. Hosts discretely present during your stay.

Guest favourite
Apartment in Harlem
4.96 out of 5 average rating, 156 reviews

Private Garden Oasis Brownstone near Central Park

Welcome to one of Harlem’s best kept secrets — a stunning brownstone apartment with your own private garden patio, something almost impossible to find in New York City. Step outside your door onto a lush, tree-lined private patio with seating, a hammock, and total privacy. Whether you’re having morning coffee surrounded by greenery or unwinding after a long day in the city, this outdoor space is unlike anything else you’ll find on Airbnb in Manhattan.

Guest favourite
Apartment in Hell's Kitchen (Clinton)
4.95 out of 5 average rating, 59 reviews

FIFA, King Bed|Walk to Times Square & Broadway

🏡 Welcome to our apartment in Hell’s Kitchen featuring a king bed and a queen sofa bed, comfortably accommodating up to 4 guests. Pack & Play is available in the apartment. ☕️ Enjoy a fully equipped kitchen with a Nespresso machine and Airfryer, perfect for home-style meals and your morning coffee. 🎭 Ideally located with easy access to Times Square, Broadway theaters, and multiple subway lines for seamless travel around NYC.

Guest favourite
A cozy office space features an exposed brick wall with wooden beams overhead. A light-colored sofa is positioned next to a glass coffee table. Natural light filters through sheer curtains, while shelves display decorative items and framed prints. A potted plant adds a touch of greenery.
Townhouse in Astoria
4.95 out of 5 average rating, 42 reviews

Modern Industrial Cozy NYC Loft

Very unique and one of a kind space in a 100 year old exposed brick townhouse, with Mid-Century Style, exposed beams, massive ceilings, all new modern finishes, appliances, and state of the art technology. This home also offers a massive backyard with outdoor living space, seating area, dining, grill, and privacy for time to relax, unwind, and enjoy some downtime with your friends and family.

Guest favourite
A spacious living area is arranged with a large sectional sofa facing expansive windows that showcase stunning views of the city skyline and the waterfront at sunset. A low coffee table sits in the center, surrounded by elegant decor and stylish seating.
Apartment in Hudson Yards
4.93 out of 5 average rating, 97 reviews

Flat with an amazing view!

Located smack dab in the center of Manhattan you can get anywhere in the city within minutes. Located in the popular New Hudson Yards developent area this stylish, new apartment gives you peace and tranquilty while at home but steps from the hustle and bustle of the city when you step outside. Apartment features full kitchen, washer dryer, king sized bedroom and gym within the building.

Superhost
A bright living area is highlighted by floor-to-ceiling windows offering expansive views of the city skyline. A cozy sofa is positioned next to a wooden coffee table. A dining table with modern chairs is set against a window, complemented by a vase of fresh flowers.
Apartment in Lincoln Square
4.91 out of 5 average rating, 58 reviews

Stunning view - Columbus Circle area/Lincoln Sq

Beautiful, clean and stylish 1-bedroom apartment in Lincoln Center with a stunning wrap-around view of the Hudson River, downtown Manhattan, and Broadway/Central Park. Modern building near many attractions! The apartment has a great layout and is spacious. Come enjoy Manhattan in a peaceful area but steps away from major attractions.

Guest favourite
A cozy bedroom features a spacious bed adorned with soft linens and decorative pillows. Adjacent nightstands with table lamps provide warm lighting. Elegant framed artwork decorates the walls, while light curtains frame the window, allowing natural light to softly illuminate the room.
Apartment in Harlem
4.95 out of 5 average rating, 40 reviews

Brownstone 2 Bed with Private Backyard near Subway

YOU HAVE FOUND THE RIGHT PLACE! Ideally situated for both academics and sports enthusiasts, our property is a 9-minute walk from Columbia University and 3 minutes from the subway. Enjoy seamless transit across the city and reach the FIFA World Cup 2026 at MetLife Stadium in just 27 minutes.

Popular amenities for Upper West Side holiday rentals

When is the best time to visit Upper West Side?

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Avg. price$259 NZD$255 NZD$264 NZD$274 NZD$306 NZD$323 NZD$315 NZD$289 NZD$304 NZD$304 NZD$294 NZD$267 NZD
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Quick stats about holiday rentals in Upper West Side

  • Total holiday rentals

    Explore 2,480 holiday rentals in Upper West Side

  • Verified guest reviews

    Over 39,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    590 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 810 rentals that welcome pets

  • Holiday rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    1,110 properties have a dedicated workspace

  • Wi-Fi availability

    2,440 of Upper West Side holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym and BBQ grill across Upper West Side rentals

  • 4.7 Average rating

    Upper West Side stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Upper West Side's top spots, include The Metropolitan Museum of Art, American Museum of Natural History, and Solomon R. Guggenheim Museum

Destinations to explore