Upper West Side holiday homes

We found 986 holiday rentals — enter your dates for availability

Discover a selection of 15 homes, 339 apartments 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.
  • 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Upper West Side

  • Family-friendly activities: The Upper West Side is ideal for families, featuring parks and attractions suitable for all ages.
  • Cultural experiences: Explore renowned art museums and iconic landmarks that showcase the area's rich history.
  • Urban parks: Enjoy the green spaces perfect for picnics and leisurely strolls amidst the city's hustle.
  • Local eateries: Savor diverse culinary delights at charming cafes and restaurants throughout the neighbourhood.
  • Lively atmosphere: Experience the vibrant community with friendly locals and a lively street scene.

Top attractions near Upper West Side

The Upper West Side in New York City is perfect for families and those keen on city life and outdoor adventures. Highlights include urban parks, art museums, and iconic skyscrapers, all providing rich cultural experiences. While exploring the area, don't miss nearby attractions and sights, including the Upper East Side, which offers even more to discover. You'll find plenty of activities suitable for everyone in this vibrant neighbourhood.

  • Times Square: A vibrant hub of entertainment and energy, Times Square is renowned for its dazzling billboards and bustling atmosphere. It's a must-visit for its iconic city vibes, just 3.2km from the Upper West Side.
  • Central Park: A stunning urban oasis, Central Park offers lush greenery and recreational activities, perfect for families and outdoor enthusiasts. Located a mere 966m from the Upper West Side, it’s a refreshing escape from city life.
  • Broadway: Famous for its world-class theatre productions, Broadway embodies the essence of New York's cultural scene. Just 3.2km from the Upper West Side, it’s a place where city vibes come alive through unforgettable performances.

Things to do recommended for couples

Planning a romantic getaway in the Upper West Side? Enjoy a night of exquisite music at Carnegie Hall, unwind with a rejuvenating treatment at SoJo Spa Club, or indulge in luxury at the Metropolitan Club. Each experience offers a unique way to connect and create lasting memories together.

Things to do recommended for families

During your family vacation in the Upper West Side, explore the Hayden Planetarium for a stellar experience, catch a game at Yankee Stadium for a sporty vibe, and have a splash at DreamWorks Water Park for thrilling adventures. There's something for everyone.

Things to do recommended for groups

Catch a show at the Al Hirschfeld Theatre or Lyceum Theatre for a touch of culture and entertainment. Afterwards, explore Macy's for a fun shopping experience, perfect for groups looking to enjoy the vibrant atmosphere of the Upper West Side.

*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 planning a trip with a group, family, pets, or are considering an extended stay, be sure to prioritise your preferences when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Upper West Side with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area 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 kids can be quite a task. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s helpful to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Upper West Side: For many families, a holiday wouldn’t feel complete without their furry companion by their side. 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 that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include extras like a car park, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Upper West Side

The Upper West Side is a vibrant, family-friendly neighbourhood perfect for an exciting city getaway. Stroll through tree-lined streets, visit iconic landmarks, and enjoy the local eateries. Nearby, you’ll find the charm of downtown Manhattan, ideal for romantic escapades or exploring elite shopping spots. With a lively atmosphere and friendly locals, this urban oasis offers a unique blend of culture and scenery that will make your holiday unforgettable.

  • New York: New York City is a bustling metropolis that serves as an iconic backdrop for your holiday. The Upper West Side, where you'll be based, is a vibrant neighbourhood filled with cultural landmarks and green spaces. Visitors flock here for an array of experiences—be it family outings, city exploration, or business engagements. You can easily enjoy shopping in diverse areas, catch a show in world-famous theatres, or revel in the electrifying atmosphere of arena entertainment. Notable attractions include the nearby Central Park, Lincoln Center for the Performing Arts, and various historic squares that encapsulate the city’s rich history.
  • Manhattan: As a prominent borough of New York City, Manhattan is located a mere 483m from the Upper West Side. This dynamic area is renowned for its iconic skyline and cultural offerings. Families, tourists, and business travellers alike can find something to suit their interests. With its plethora of shopping options, engaging theatres, and top-notch entertainment venues, Manhattan provides a bustling urban experience. Highlights include Times Square, the Museum of Modern Art, and the historic Grand Central Terminal, all easily accessible for a day of exploration.
  • Midtown: Midtown is a vibrant neighbourhood situated 3.2km away from the Upper West Side. Known for its commercial and entertainment hubs, this area is perfect for families, city explorers, and business visitors. Midtown boasts a wealth of shopping opportunities and theatrical performances, as well as famed arenas that host exhilarating events. Key attractions include the Empire State Building, the bustling Rockefeller Center, and the iconic Broadway theatres, ensuring a memorable experience in the heart of New York City.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.6°F (-0.2°C)Light RainMostly SunnyAverage
February33.1°F (0.6°C)Light RainMostly SunnyAverage
March40.5°F (4.7°C)Light RainMostly SunnyAverage
April51.1°F (10.6°C)Light RainMostly SunnySlightly High
May61.3°F (16.3°C)Light RainMostly SunnyAverage
June70.2°F (21.2°C)Light RainMostly SunnyAverage
July76.8°F (24.9°C)Light RainMostly SunnySlightly High
August75.4°F (24.1°C)Light RainMostly SunnyAverage
September68.7°F (20.4°C)Light RainMostly SunnySlightly High
October57.9°F (14.4°C)Light RainMostly SunnySlightly Low
November46.0°F (7.8°C)Light RainMostly SunnySlightly Low
December37.9°F (3.3°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Ready to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to some excellent savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy way to plan new trips, continue from where you last stopped, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Upper West Side?
Apartments are the most popular style of holiday home in Upper West Side, according to our data. Even if you've got a different idea about what you'd like, Bookabach has holiday homes in loads of sizes and shapes. Compare our options to find your ideal match.
How much does it cost to rent a holiday home in Upper West Side?
Length of stay, property type and season are some of the things that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From cosy chalets to expansive luxury villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Upper West Side?
The average price for a holiday home by the beach in Upper West Side depends on when you're going and the style and size of property you're looking for. You can quickly and easily find prices on Bookabach by entering your travel dates and destination. Then use our filter tool to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday homes in Upper West Side?
With 258 properties that host four-legged guests, your furry little friend can join you on your Upper West Side holiday. Use our filter tool to search our pet-friendly holiday homes and find the pawfect pad on Bookabach.
Can I rent a house with a pool in Upper West Side?
Grab your swimsuit and swim ring, because there are three houses with a private pool in Upper West Side. Base yourself at one of these sought-after holiday homes and let every day be a pool day. Simply enter your travel dates into Bookabach, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Upper West Side?
When it comes to home amenities that guests prefer in Upper West Side, a firepit, a garden and mountain views are at the top of the list. With Bookabach holiday homes, you'll find options to match your taste and style, whether you're taking a trip with your partner, your friends or even pets.
Are there large group holiday homes in Upper West Side?
Upper West Side has 27 holiday properties that can fit 10 or more guests. These stays come with all the space you need to enjoy good times with family and friends.
Are there holiday homes in Upper West Side that welcome kids?
With 248 family-friendly holiday homes available in Upper West Side, there's never been a better time to introduce the kids to the excitement of travel. Simply check our "Properties good for families" filter box to locate stays packed with conveniences perfect for families on the move, such as living rooms, private pools, hot tubs and entertainment areas.
What are the top attractions for families in Upper West Side?
Keeping the kiddos entertained during your stay in Upper West Side is simple with these fabulous family-friendly attractions:

  • Rockefeller Centre
  • American Museum of Natural History
  • Chelsea Piers

Are there one-bedroom holiday homes in Upper West Side?
Yes, you can choose from 148 one-bedroom homes in Upper West Side. Whether you're on the lookout for a cosy chalet or a cabin, Bookabach's one-bedroom homes are just right if you don't require lots of space. One of the perks of having your own place? You won't ever have to share your getaway with strangers.
Can I find two-bedroom holiday homes in Upper West Side?
Pick from 61 two-bedroom homes in Upper West Side. Give your little ones the second room or fill it with a couple of your besties. There's enough space for whoever's fortunate enough to be joining in on the fun.
Are there holiday homes with WiFi in Upper West Side?
Whether you want to keep up with the headlines, send some emails or surf social media, there are 29 holiday homes with WiFi in Upper West Side. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Upper West Side?
There are 248 Bookabach holiday homes with air conditioning in Upper West Side giving you that cool, cool breeze and extra element of comfort. Just enter your desired travel dates and then use our handy filter tool to find properties with air conditioning.
How old do you have to be to rent a holiday home in Upper West Side?
The minimum age permitted can differ across properties on Bookabach, so check the rules of the holiday home in Upper West Side you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Upper West Side for?
The amount of time you can stay in an Upper West Side holiday home for is up to the property. Just enter your dates of travel to find available options that offer long-term stays. They feature the things you need to make your extended holiday more enjoyable and convenient, such as kitchens and air conditioning. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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