Upper West Side holiday lettings

We found 1,085 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Upper West Side that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include air conditioning and a pool. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Upper West Side

  • Cultural Richness: Explore iconic institutions like the American Museum of Natural History, showcasing fascinating exhibits for all ages.
  • Stunning Parks: Enjoy the beauty of Central Park, perfect for leisurely strolls, picnics, and outdoor activities.
  • Historic Brownstones: Wander through picturesque streets lined with charming historic brownstones, reflecting the neighbourhood's architectural heritage.
  • Vibrant Dining Scene: Experience a range of dining options from quaint cafes to upscale restaurants, offering diverse culinary delights.
  • Friendly Atmosphere: Embrace the welcoming vibe of the neighbourhood, ideal for families and city explorers alike.

Popular types of accommodation around Upper West Side

If you're planning a trip to the vibrant Upper West Side in New York City, you're in for a treat. This charming neighbourhood is renowned for its historic brownstones, lush parks, and cultural landmarks. Enjoy a stroll along the scenic streets, visit iconic museums, or relax in the beautiful parks. When it comes to accommodation, you'll find a range of options including furnished apartments, houses, and stylish condos, perfectly suited for your stay.

  • Apartments: The most sought-after option for holiday stays in the Upper West Side, offering a comfortable and convenient home away from home.
  • Houses: A popular choice for those seeking a unique and spacious environment, perfect for families or groups.
  • Condos: Ideal for travellers looking for modern amenities in a stylish setting, often with great views.
  • Cottages: Charming and cosy, these provide a quaint retreat amidst the urban hustle.
  • Villas: Luxurious and spacious, perfect for an indulgent getaway in the heart of the city.**

Top attractions near Upper West Side

The Upper West Side is a vibrant neighbourhood in New York City, perfect for families and those seeking a city-themed getaway. Visitors can explore stunning urban parks, renowned art museums, and impressive skyscrapers, providing a rich cultural experience. This area offers numerous attractions that cater to diverse interests, making it an ideal destination for outdoor adventures and memorable family outings.

  • Tours of the Upper West Side: Discover the charming brownstones, vibrant cultural scene, and historic architecture of this iconic neighbourhood, home to the famous American Museum of Natural History.
  • Lincoln Center for the Performing Arts: Experience world-class music, dance, and theatre at this renowned cultural complex, showcasing a variety of performances throughout the year.
  • Riverside Park: Enjoy leisurely strolls along the Hudson River, picturesque views, and ample green space for picnics and outdoor activities in this serene urban park.

Things to do recommended for couples

Discover the charm of the Upper West Side with a leisurely stroll through Central Park, followed by a romantic dinner at a quaint bistro. Don't miss a sunset cruise along the Hudson River for breathtaking views of the city skyline, creating unforgettable memories together.

Things to do recommended for families

Families can explore the American Museum of Natural History, featuring fascinating dinosaur exhibits and an impressive planetarium. Additionally, take a leisurely stroll in Central Park, where children can enjoy playgrounds, boat rides, and open spaces for picnics and games.

Things to do recommended for groups

Explore the vibrant atmosphere of the Upper West Side by visiting the American Museum of Natural History, or enjoy a leisurely stroll through Central Park. Gather your friends for a delightful meal at a local eatery or catch a show at the historic Beacon Theatre for a memorable evening.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Upper West Side

If you're travelling with a group, as a family, bringing along your pets, or seeking extended stays, it's important to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Upper West Side with a group: Take into account the number of bedrooms you require, along with features like a fully equipped kitchen or outdoor areas suitable for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Upper West Side with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Upper West Side: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Upper West Side: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features such as a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Upper West Side

The Upper West Side is a vibrant neighbourhood that offers an array of attractions perfect for families and city explorers alike. Stroll through the scenic streets lined with historic brownstones, visit the iconic Central Park, or explore the renowned American Museum of Natural History. The area boasts a friendly atmosphere, with charming cafes and restaurants that reflect the urban vibe. Whether you're enjoying a leisurely walk or engaging in cultural experiences, the Upper West Side promises an unforgettable New York adventure.

  • New York: New York City is a vibrant metropolis that embodies the essence of urban life. The Upper West Side, with its cultural richness and historic architecture, is a perfect starting point for exploring the city. Visitors can indulge in world-class shopping, enjoy a Broadway show, or take in exhilarating arena entertainment. Key attractions nearby include bustling squares and modern landmarks, such as Central Park and the American Museum of Natural History, making it a must-visit for families, business travellers, and city explorers alike.
  • Manhattan: Just 483m from the Upper West Side, Manhattan is the heart of New York City and is renowned for its iconic skyline and cultural diversity. This borough offers a plethora of activities, from shopping in upscale boutiques to experiencing live performances in its famous theatres. You’ll find numerous tourist precincts and vibrant squares, perfect for leisurely strolls or dining. Whether you’re with family or on a business trip, Manhattan provides an unforgettable urban experience.
  • Uptown: Located 1km from the Upper West Side, Uptown is a charming neighbourhood that combines outdoor adventures with urban living. It’s an ideal spot for families seeking educational experiences, as well as those looking for outdoor activities. In addition to theatres and shopping areas, Uptown features beautiful parks and public spaces, offering a delightful escape from the bustling city. With its scenic spots and local attractions, Uptown completes the perfect itinerary for any visitor to New York.

Best time to go to Upper West Side

If you're planning a trip to Upper West Side, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.6°F (-0.2°C)Light RainMostly SunnyAverageSlightly Low
February33.1°F (0.6°C)Light RainMostly SunnyAverageSlightly Low
March40.5°F (4.7°C)Light RainMostly SunnyAverageSlightly Low
April51.1°F (10.6°C)Light RainMostly SunnySlightly HighAverage
May61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
June70.2°F (21.2°C)Light RainMostly SunnyAverageAverage
July76.8°F (24.9°C)Light RainMostly SunnySlightly HighSlightly High
August75.4°F (24.1°C)Light RainMostly SunnyAverageSlightly High
September68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
October57.9°F (14.4°C)Light RainMostly SunnySlightly LowAverage
November46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
December37.9°F (3.3°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? It may be beneficial to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides you with a convenient area to plan new adventures, carry on with your existing arrangements, or review and organise your bookings. Your saved or reserved properties are now categorised into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Upper West Side?
In the Upper West Side of New York, apartments are the most prevalent type of holiday rental, with several options available throughout the neighbourhood. These apartments typically boast modern amenities, including fully equipped kitchens, spacious living areas, and often feature large windows that provide stunning views of the city or nearby parks. Many rentals are conveniently located near iconic attractions such as Central Park and the American Museum of Natural History, making them ideal for those looking to explore the vibrant culture of the area.
How much does it cost to rent a holiday home in Upper West Side?
Prices for holiday rentals in Upper West Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Upper West Side to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Upper West Side holiday house rentals?
You can find great discounts on house rentals in Upper West Side on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Upper West Side?
In the Upper West Side of New York, popular rental amenities include a fully equipped kitchen, allowing guests to prepare their own meals, as well as conveniences like a blender and a coffee or tea maker for those who enjoy their morning brews. Many properties also provide essential items such as paper towels, enhancing the home-like experience. Additionally, for those travelling with pets, several rentals permit animals, making it easier for pet owners to enjoy their stay without leaving their furry friends behind.
Are there any Upper West Side holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Upper West Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly holiday rentals in Upper West Side?
In the Upper West Side of New York, there are several pet-friendly holiday rentals available, making it an excellent choice for travellers with furry companions. This vibrant neighbourhood offers a mix of modern apartments and classic brownstones, many of which feature amenities such as fully equipped kitchens, spacious living areas, and easy access to laundry facilities.

One of the highlights of the Upper West Side is its proximity to several parks, including the iconic Central Park and Riverside Park, both of which are superb for leisurely strolls and outdoor activities with pets. Central Park, in particular, offers expansive green spaces, walking trails, and designated off-leash areas, allowing dogs to roam freely while their owners enjoy the scenic surroundings.

Additionally, the Upper West Side is home to a variety of pet-friendly cafes and shops, providing convenient options for dining and shopping while accommodating your pet.
Can I find long-stay holiday rentals in Upper West Side?
A long-stay holiday rental in Upper West Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Upper West Side for a holiday rental?
The best time to visit the Upper West Side for a holiday rental is during the peak season from July to September. This vibrant period attracts many tourists, as the neighbourhood buzzes with energy, offering a delightful mix of outdoor activities, cultural events, and iconic sights. The warm summer weather makes it great for leisurely strolls in Central Park or enjoying a picnic near the Great Lawn, with temperatures typically ranging from 20 to 30 degrees Celsius.

July stands out as the most popular month to explore this iconic area. Visitors can take part in the lively option, attend open-air concerts, and take advantage of the many street fairs and festivals that take place. The proximity to landmarks like the American Museum of Natural History and the historic architecture adds to the allure of a summer visit.

For those looking for a more budget-friendly option, November presents a quieter yet charming time to experience the Upper West Side. The crisp autumn air offers a refreshing backdrop for exploring the neighbourhood's quaint cafés and shops, while the fall foliage enhances the beauty of nearby parks.

Ultimately, your choice of when to visit will depend on your preferences for lively summer activities or the peaceful allure of autumn colours.
How early should I book a Upper West Side holiday rental?
Book your Upper West Side holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Upper West Side, New York, United States of America?
In the Upper West Side, visitors can enjoy a variety of attractions that showcase the neighbourhood's cultural and historical significance. Central Park, with its expansive green spaces, meandering pathways, and iconic landmarks like Bethesda Terrace, is a major highlight, offering opportunities for leisurely strolls and recreational activities.

The American Museum of Natural History is another key attraction, renowned for its vast collection of exhibits, including the impressive dinosaur fossils and the Rose Centre for Earth and Space. Just a short walk away, the Lincoln Centre for the Performing Arts stands as a cultural hub, featuring world-class performances in music, dance, and theatre.

Additionally, the Upper West Side is home to the historic Dakota building, famous for its architectural beauty and as the former residence of John Lennon.
Can I change or cancel my Upper West Side home rental booking on Vrbo?
To find Upper West Side holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Upper West Side holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas