Upper West Side holiday lettings

We found 1,078 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Upper West Side by choosing from 64 houses, 384 apartments and other holiday rentals. 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.

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.

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.

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

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.

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 accommodation in Upper West Side?
Apartments are the most popular style of holiday rental in Upper West Side, according to our data. Even if you've got a different idea about what you'd like, Vrbo 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 rental 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 Vrbo holiday rentals provide unbeatable value.
How much does it cost to rent a beach house in Upper West Side?
The average price for a holiday rental 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 Vrbo 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 rentals 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 rentals and find the pawfect pad on Vrbo.
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 Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Upper West Side?
When it comes to rental amenities that guests prefer in Upper West Side, a firepit, a garden and mountain views are at the top of the list. With Vrbo 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 rentals 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 rentals in Upper West Side that welcome kids?
With 248 family-friendly holiday rentals 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 rentals in Upper West Side?
Yes, you can choose from 148 one-bedroom rentals in Upper West Side. Whether you're on the lookout for a cosy chalet or a cabin, Vrbo's one-bedroom rentals 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 rentals 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 rentals 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 Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Upper West Side?
There are 248 Vrbo 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 rental in Upper West Side?
The minimum age permitted can differ across properties on Vrbo, so check the rules of the holiday rental in Upper West Side you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Upper West Side for?
The amount of time you can stay in an Upper West Side holiday rental 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 Vrbo holiday rentals may also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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