Upper West Side holiday lettings

We found 1,127 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.

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Why visit Upper West Side

  • Cultural richness: Discover a vibrant tapestry of art museums and historic sites, showcasing the area's rich heritage.
  • Urban parks: Enjoy leisurely strolls or picnics in picturesque parks like Central Park, perfect for families and outdoor enthusiasts.
  • Diverse dining: Savor a variety of cuisines in charming restaurants and cafés, offering something for every palate.
  • Family-friendly activities: Engage in numerous attractions tailored for families, ensuring fun for all ages.
  • Welcoming atmosphere: Experience the friendly locals and lively neighbourhood vibe, making you feel at home in the city.

Popular types of accommodation around Upper West Side

If you're planning a getaway to the Upper West Side, the next step is selecting the perfect accommodation. This vibrant area offers a variety of options, including charming apartments, spacious houses, and modern condos. Whether you're searching for apartment rentals or house rentals, you'll find delightful choices that suit your needs. Explore the best Upper West Side vacation rentals and enjoy a comfortable stay in this iconic part of New York City.

  • Apartments: The most sought-after accommodation option in the Upper West Side, offering a home-away-from-home experience with convenient amenities.
  • Houses: Ideal for those seeking extra space and privacy, these homes cater to families and groups looking for a comfortable stay.
  • Condos: A popular choice for visitors, condos combine the comforts of home with access to shared facilities in stylish settings.
  • Cottages: Quaint and charming, cottages provide a cosy atmosphere for a relaxing getaway.
  • Villas: Luxurious and spacious, villas offer a high-end experience for those looking to indulge during their stay.**

Top attractions near Upper West Side

The Upper West Side is perfect for families and city enthusiasts alike, offering a delightful mix of urban parks, art museums, and iconic skyscrapers. Visitors can immerse themselves in the rich culture and vibrant atmosphere, enjoying various attractions that cater to both family experiences and urban exploration. This area promises a memorable vacation filled with engaging activities and sights for all ages.

  • Times Square: A bustling hub of energy, Times Square is known for its bright lights, vibrant atmosphere, and iconic billboards. It's an essential experience for anyone looking to soak in the city's dynamic culture, located 1.2km from the Upper West Side.
  • Central Park: This expansive green oasis is perfect for families and outdoor enthusiasts. Enjoy leisurely strolls, picnics, and recreational activities in a serene environment, situated just 373m away from the Upper West Side.
  • Broadway: Renowned for its world-class theatre productions, Broadway offers an unforgettable night out filled with captivating performances and city vibes, also located 1.2km from the Upper West Side.

Things to do recommended for couples

Looking for a romantic getaway in the Upper West Side? Enjoy a splendid evening at Carnegie Hall, indulge in relaxation at SoJo Spa Club, or experience luxury at the Metropolitan Club. These charming spots are perfect for creating unforgettable memories together.

Things to do recommended for families

Your family will delight in the Hayden Planetarium, just half 1.6km away, for a fascinating cosmic experience. Enjoy ice skating at the Rink at Rockefeller Center, located 1.2km away, or catch a thrilling game at Yankee Stadium, a mere 2.5km from Upper West Side.

Things to do recommended for groups

Groups visiting the Upper West Side can enjoy a shopping spree at Macy's, just 1.9km away, or catch a family-friendly show at the nearby Broadway Theatre, located 1.2km from the area. Don't forget to visit Tiffany & Co., also 1.2km away, for a touch of luxury.

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

If you’re travelling with a group, family, or pets, or if you’re considering longer stays, it’s important to filter your options according to your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Upper West Side with a group: Think about how many bedrooms you will require, as well as features like a fully equipped kitchen or outdoor space for socialising with your group. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Upper West Side with young kids: Travelling with young children can present some challenges. It’s important to prioritise their comfort and safety, as well as access to suitable facilities, such as a private swimming pool. Additionally, it’s wise to take into account your location in relation to family-friendly attractions.
  • Taking your pets with you to Upper West Side: For many families, a holiday isn't truly fulfilling unless their four-legged companion is by their side. If you can relate to this, explore the Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Upper West Side: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect destination. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Upper West Side

The Upper West Side offers a delightful blend of urban charm and family-friendly atmospheres, making it an ideal destination for a memorable holiday. Explore the vibrant nightlife, picturesque parks, and welcoming locals while enjoying the nearby attractions. Neighbouring areas provide ample rental options, ensuring a comfortable stay as you immerse yourself in the rich cultural tapestry of this iconic New York neighbourhood. Experience the perfect balance of city vibes and outdoor adventures in this bustling locale.

  • New York: New York is a bustling metropolis located 1.2km from the Upper West Side, renowned for its vibrant energy and diverse experiences. This iconic city offers a plethora of activities suitable for families, business travellers, and those seeking a rich urban adventure. Explore the renowned shopping areas, catch a Broadway show, or enjoy various entertainment options at local arenas. Highlights include famous tourist precincts and modern squares, making it a must-visit for those looking to immerse themselves in the heart of city life.
  • Manhattan: Just 186m from the Upper West Side, Manhattan is a dynamic borough that encapsulates the essence of New York City. Visitors flock here for family-friendly activities, business opportunities, and a taste of the city's unique culture. The area is filled with shopping venues and theatres, ensuring there's always something to see and do. Local attractions also include popular squares and vibrant tourist precincts, making Manhattan an essential stop on your exploration of New York.
  • Midtown: Situated 1.2km from the Upper West Side, Midtown is a lively neighbourhood that draws visitors for its family-oriented activities and vibrant city atmosphere. This area is well-known for its shopping hotspots and world-class theatres, providing ample opportunities for entertainment. Visitors can also enjoy iconic landmarks and modern squares that define the Midtown experience. Whether you're here for leisure or business, Midtown offers a perfect blend of excitement and convenience for all types of travellers.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 some pounds on your next getaway? It might be worth considering flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the ideal Vrbo property that fits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. The properties you've saved or reserved are now categorized into Potential, Upcoming, or Current Trips. To discover more about 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.

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