
Holiday houses in Upper West Side
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Quick stats about holiday rentals in Upper West Side

Total holiday rentals
Explore 2,560 holiday rentals in Upper West Side

Verified guest reviews
Over 39,160 verified reviews to help you choose

Family-friendly holiday rentals
610 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 790 rentals that welcome pets

Holiday rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
1,220 properties have a dedicated workspace

Wi-Fi availability
2,500 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
Top-rated holiday rentals in Upper West Side
Guests agree: these stays are highly rated for location, cleanliness and more.

FAB Garden Guest Suite W/Garden nr Central Park!
SPECTACULAR GARDEN GUEST SUITE IN TOWNHOUSE WITH GARDEN ENTRANCE. WE ARE SUPERHOSTS! Read our reviews! WE ARE A LEGAL AIRBNB IN NYC! Tranquil Suite with semi-private entrance and a GARDEN in a beautiful townhouse on the Upper West Side of Manhattan, very close to Central Park. Complete with a queen-sized bed, flat-screen TV, plus a kitchenette and a gorgeous bathroom featuring a steam shower and body jets. BLACKOUT BLINDS ON ALL WINDOWS/DOORS! NETFLIX, HBO, PRIME, and CABLE! TWO GUEST MAX!

Central Upper West Side Room
Enjoy easy access to everything from our centrally located home. Included in the listing is as much coffee as you can stomach, courtesy of our Nespresso machine. Just a short block to the 1 subway train, you will be anywhere on the island in no time. Steps away from Riverside Park where spectacular Hudson River views and the most beautiful NYC sunsets await. A 10 minute stroll to the east, and you’re in iconic Central Park. Come as a tourist, live like a local, leave as a more informed tourist.

Midtown 2 Bed Full Kitchen
Perfect location to start a journey in NYC. Midtown East 2 blocks from UN. 1 Queen bed in each room & sofa bed, sleeps comfortably up to 5 ppl. Sofa bed can be made up upon request, extra linens in closet. Pet Friendly $250 nonrefundable fee to be paid at property. Fully furnished apartment, with 24/7 concierge, gym, & laundry services. Has an amazing rooftop bar in the building. All guests names must be listed, ID required to check in. We will make your stay very pleasant and comfortable!

Modern Studio, 1 Queen Bed near Grand Central
Nester Finn Grand Central offers modern comfort and the feeling of home in the heart of Manhattan, just a short walk from Grand Central Terminal and the city’s main transit links. The property features a collection of renovated apartments, ranging from studios and one-bedroom layouts. Each space is designed for comfort and practicality, with a fully equipped kitchen, modern bathroom and TV streaming. Select units can be booked as connecting apartments for added space and flexibility.

Stylish 4 Bedroom Gem On The Upper West Side
Experience classic New York charm in this spacious 4-bedroom apartment nestled in the Upper West Side. This residence combines the allure of pre-war architecture with modern comforts. Featuring high ceilings, hardwood floors, and elegant details, this stylish retreat offers comfort and character just steps from Central Park, museums, cafes, and subway lines. Perfect for families or groups, enjoy a true NYC stay in one of Manhattan’s most iconic neighborhoods.

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.

Vintage Luxe | King Bed + Patio | Subway + Yankees
Welcome to Vintage Luxe, your NYC escape inside a beautifully restored 1894 Frederick Dinkelberg landmark in historic Sugar Hill. Wake up in a king bed, enjoy coffee on your private patio, then explore the city with the 145 St Subway just 1 minute away and Yankee Stadium nearby. Come home to preserved woodwork, bay windows, a decorative fireplace, full kitchen, Smart TVs, fast WiFi, a workspace, and two comfortable sofas that can also be slept on.

Studio Queen Gourmet | Placemakr Wall Street
Welcome to Placemakr Wall Street, located in the heart of New York's buzzing financial district. Furnished with hardwood floors, stylish finishes, and many modern conveniences, this is the perfect place to stay while exploring Manhattan and the rest of the Big Apple. Indulge in highly-rated, nearby restaurants and take in the sights of One World Trade Center and South Street Seaport, all within close reach of Placemakr Wallstreet.

Mint House 70 Pine by Kasa | Accessible Studio
Mint House 70 Pine by Kasa blends style and function in Manhattan’s Financial District. Choose from hotel rooms and suites with kitchenettes or full kitchens, with access to amenities including the fitness center and meeting spaces, and on-site Michelin-starred dining at Crown Shy and SAGA. Our tech-enabled rooms and suites offer self check-in at 4pm. We provide 24/7 on-site Front Desk services, including guest support by text.

Private Manhattan Retreat | Sauna, Yard + King Bed
Imagine spending the day exploring Manhattan, walking by the Hudson River, grabbing coffee, seeing the city, then coming back to your own private retreat. You step inside, relax in the sauna, put on a movie, stretch out on the king bed, or sit outside in the backyard on the hammock or swing chair. It's cozy, romantic, and peaceful, the perfect place to slow down and enjoy a special New York stay..

Designer Duplex Loft Central Park West
True NYC living at our stylish 3 Bedroom, 2 Bathroom Duplex Home. A dramatic spiral staircase dividing the loft in half, contemporary artwork, comfortable decor, and full living essentials - feel right at home with the ability to cook, relax, and enjoy true NYC living. Situated just a block from Central Park West with easy subway access just steps away.

Designers Upper East Side 2 Bedroom.
Welcome to your luxurious Manhattan retreat nestled in the heart of the prestigious Upper East Side! This exquisite two-bedroom apartment boasts elegance, sophistication, and modern comfort, making it the perfect getaway for travelers seeking an unforgettable New York experience. Only one flight up and facing the courtyard. 2 people max.
Popular amenities for Upper West Side holiday rentals
Stay near Upper West Side's top sights
Other great holiday rentals in Upper West Side

1892 Brownstone on Landmarked Block

Tranquil Midtown Sanctuary - Full Bed

Near Theater District & Times Square + Dining

Upper Westside Brownstone Garden Apartment

Private bedroom in Manhattan Upper East Side

Charming

Walk to Times Square with Free Breakfast & Wine

Two Bathroom Suite steps from Central Park
Destinations to explore
- Rentals with pools Upper West Side
- Condo rentals Upper West Side
- Townhouse rentals Upper West Side
- Family-friendly rentals Upper West Side
- Waterfront rentals Upper West Side
- Hotel rooms Upper West Side
- Rentals with breakfast Upper West Side
- House rentals Upper West Side
- Boutique hotels Upper West Side
- Apartment rentals Upper West Side
- Rentals with a hot tub Upper West Side
- Pet-friendly rentals Upper West Side
- Times Square
- Central Park Zoo
- Asbury Park Beach
- Mountain Creek Resort
- Jones Beach
- Columbia University
- Yankee Stadium
- Belmar Beach
- American Dream
- MetLife Stadium
- New York City Center
- Rockefeller Center
- Long Branch Beach
- United Nations Headquarters
- Manasquan Beach
- Empire State Building
- Bear Mountain State Park
- Barclays Center
- Bryant Park
- Citi Field
- Statue of Liberty
- Grand Central Terminal
- Brooklyn Bridge
- Radio City Music Hall





