Upper West Side holiday rentals

We found 1,083 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.
  • Peace of mind

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  • More quality time

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  • 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

  • Urban parks: Enjoy leisurely strolls in picturesque parks that offer a serene escape from the city hustle.
  • Cultural landmarks: Explore renowned museums and art galleries that showcase diverse artistic expressions.
  • Architectural gems: Admire iconic skyscrapers and historic buildings that define the neighbourhood's character.
  • Family-friendly atmosphere: Discover activities and attractions suitable for visitors of all ages, ensuring a delightful experience.
  • Vibrant dining scene: Savour a diverse array of culinary delights from local eateries and restaurants.

Popular types of accommodation around Upper West Side

Experience the charm of Upper West Side with its diverse holiday rentals. Our selection includes apartments, private holiday homes and cosy condos, ensuring there's a friendly accommodation option for every traveller. Located in the heart of Upper West Side, our offerings provide the perfect base to explore local attractions and enjoy a memorable New York holiday. Find the best accommodation, holiday rentals and short stay options for your ideal stay in this vibrant neighbourhood.

  • Apartments: Enjoy the timeless charm of city-centre flats, offering modern comforts and convenience in the heart of Upper West Side.
  • Private Holiday Homes: Relish the privacy and space of standalone dwellings, perfect for a cosy retreat in a bustling urban setting.
  • Condos: Experience stylish living in contemporary condominiums, blending luxury with practicality.
  • Cottages: Discover quaint, characterful cottages, ideal for a peaceful escape from the city's pace.
  • Caravan Parks: Embrace the adventurous spirit with caravan parks that cater to those seeking a unique, mobile holiday experience.**

Top attractions near Upper West Side

Discover the charm of Upper West Side, where urban parks, art museums, and iconic skyscrapers create a vibrant cityscape perfect for family adventures and cultural exploration. Enjoy the blend of outdoor experiences and cultural attractions in this lively neighbourhood, designed for those seeking a memorable city-themed holiday. The area offers ample opportunities to explore both local heritage and modern urban life, ensuring a delightful stay with diverse attractions for every visitor.

  • Times Square: Modern square with vibrant city vibes, located 3km from the Upper West Side, offering a dynamic urban experience.
  • Central Park: Urban park with family-friendly, outdoor ambience, situated 966m from the Upper West Side, perfect for leisurely strolls.
  • Grand Central Terminal: Iconic landmark exuding cultural vibes, positioned 3km from the Upper West Side, a must-see for history and architecture enthusiasts.

Things to do recommended for couples

Seeking a romantic getaway in the Upper West Side? Delight in a leisurely walk through Central Park, savour a candlelit dinner at a charming bistro, or catch a show at the iconic Lincoln Center for an unforgettable evening together. Embrace the area's vibrant culture and create lasting memories.

Things to do recommended for families

Families visiting the Upper West Side can explore the delightful American Museum of Natural History, featuring fascinating exhibits and a planetarium. Enjoy a leisurely stroll in Central Park, where children can play, and experience the enchanting Carousel for a fun-filled day.

Things to do recommended for groups

Groups visiting the Upper West Side can enjoy a leisurely stroll through Central Park, visit the American Museum of Natural History, and dine at local eateries offering diverse cuisines. Don't miss a Broadway show for a truly unforgettable evening experience.

*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

Whether you're journeying with a group, travelling as a family, accompanied by your pets or seeking extended stays, ensure that you filter by the appropriate criteria. Here are some Stayz booking pointers for you.

  • Traveling to Upper West Side with a group: Consider how many bedrooms you require, along with amenities like a fully-equipped kitchen or an outdoor area for group get-togethers. Luckily, Stayz allows you to filter for these features and many others.
  • Traveling to Upper West Side with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with ensuring that there are suitable amenities, such as a private swimming pool. Additionally, it’s wise to take into account your closeness to attractions that are suitable for families.
  • Taking your pets with you to Upper West Side: For many, a family holiday isn’t complete without their four-legged companion in tow. If this resonates with you, then explore Stayz properties that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring every member of the family feels at home.
  • Planning for a long term stay visiting Upper West Side: If you are seeking holiday lets offering discounts for stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly discover and save on monthly rentals. Consider including a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Upper West Side

Discover the charm of Upper West Side, New York, where urban sophistication meets family-friendly allure. Enjoy leisurely walks through tree-lined avenues, explore cultural landmarks, and savour the vibrant cityscape from the upper floors. This neighbourhood offers a blend of artistic expression and a warm, inviting atmosphere, making it perfect for both city explorers and those seeking a relaxed, outdoor holiday experience.

  • New York, Manhattan, Midtown: New York is a bustling metropolis that offers a diverse range of experiences for family, city-themed, and business-themed travellers. Situated within this dynamic cityscape, the Upper West Side is perfectly positioned to enjoy the vibrant attractions of New York. Visitors can explore a variety of popular activities, including shopping areas, theatres and arena entertainment facilities. The city is adorned with well-known landmarks such as tourist precincts, expansive squares and modern plazas, all of which contribute to an energetic and cosmopolitan atmosphere.
  • Manhattan: As a prominent borough, Manhattan is located 483m from the Upper West Side. This vibrant area is known for its rich cultural tapestry and dynamic urban life, appealing to families, city enthusiasts and business travellers alike. Its close proximity makes it an ideal destination for a quick jaunt. Enjoy a day out exploring its renowned shopping districts, theatres and entertainment venues, while also taking in local attractions like bustling tourist precincts, charming squares and contemporary modern squares.
  • Midtown: Midtown, situated 3km from the Upper West Side, is a lively neighbourhood that promises a mix of family-friendly attractions and a vibrant urban vibe. The area is celebrated for its diverse cultural offerings, including shopping areas, theatres and arena entertainment facilities. Visitors can immerse themselves in the local scene by exploring nearby tourist precincts, historic squares and modern plazas, each offering a unique slice of New York’s dynamic urban charm.

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 Stayz is simple

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can lead to significant savings, given that prices fluctuate. Moreover, opting for a longer stay can often result in even better deals. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board provides you with a convenient platform to plan new journeys, manage your existing arrangements, or review your bookings. The properties you’ve saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.stayz.com.au/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, Stayz 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 Stayz 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 Stayz 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 Stayz.
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 Stayz, 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 Stayz 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, Stayz'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 Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Upper West Side?
There are 248 Stayz 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 Stayz, 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 Stayz holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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