Poughkeepsie Vacation Packages 2026 from $945

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Your Poughkeepsie Vacation

Design your ideal adventure with a Poughkeepsie vacation package tailored to your needs and preferences. Rich history, cultural experiences and spectacular views are just a few of the things that await you in this historic city. Any trip to Poughkeepsie needs a well-designed itinerary. Fill yours with big-name attractions like Marist College, Vassar College and Culinary Institute of America. A couple of clicks is all it takes to create the perfect Poughkeepsie vacation on Expedia.

The Latest Poughkeepsie vacation packages

Price found within the past 48 hours. Click for updated prices.

Modern Comfort in the Heart of NYC

Southeast Yonkers

Save 100% on your flight

$945

per person

Dec 10 - Dec 14

found 9 hours ago

Roundtrip flight included

San Juan (SJU) to White Plains (HPN)

3.6/10 (4 reviews)

It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.

Reviewed on Jun 29, 2026

Luxury NY Home 3BR with Easy Parking

Southeast Yonkers

Save 100% on your flight

$1,919

per person

Dec 10 - Dec 14

found 14 hours ago

Roundtrip flight included

San Juan (SJU) to White Plains (HPN)

3/10 (4 reviews)

Luxury NY Home with Free Parking

Save 100% on your flight

$2,361

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

San Juan (SJU) to White Plains (HPN)

8/10 Very Good! (1 review)

Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.

Reviewed on Nov 8, 2025

Modern Luxury Home w GameRoom & Parking

Southeast Yonkers

Save 100% on your flight

$1,591

per person

Dec 11 - Dec 13

found 21 hours ago

Roundtrip flight included

San Juan (SJU) to White Plains (HPN)

5/10 (12 reviews)

Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ... Will use this management and property owner in our upcoming short terms rentals.....

Reviewed on Sep 13, 2026

Luxury NYC Home Game Room Free Parking

$1,661

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to White Plains (HPN)

4/10 (1 review)

After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is that there was a plumbing problem and they would get us to another property from the original property manager and Expedia NOT doing a thing to help 4 of us stranded with no place to stay, we got to the other property. The new property was fine, but the most upsatting thing was dealing with Expedia trying to get a place for us to stay. Expedia tried saying they would cancel the accommodations and get us a Hotel but we would have to pay for the hotel and then wait for any credits or refund on our original booking. HIGHLY unacceptable by Expedia customer service. I am a GOLD member and spend quite a few thousand dollars a year for both business and pleasure and they did NOTHING to make me feel they were taking care of us. We basically lost a day of full work which cost my business over $1500 in non productive work.

Reviewed on May 4, 2026

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Where to stay in Poughkeepsie

Find the best Poughkeepsie areas and neighborhoods for the activities you enjoy most. Learn more about Poughkeepsie

A nighttime view of a bridge with colorful lights reflecting on the water.

Arlington

1 out of top 10 points of interest in this area

You'll enjoy the coffeehouses and art galleries in Arlington. You might want to make time for a stop at Frances Lehman Loeb Art Center or Vassar Golf Course.

A marina with several boats docked at sunset.

Poughkeepsie Waterfront

2 out of top 10 points of interest in this area

You'll enjoy the restaurants and riverfront in Poughkeepsie Waterfront. You might want to make time for a stop at Walkway Over the Hudson State Historic Park or Mid-Hudson Bridge.

A large suspension bridge spanning a river, surrounded by dense greenery.

Crown Heights

Visitors to Crown Heights enjoy its coffeehouses, and if you want to do some exploring, Hudson River is worth a stop.

A historic stone building with a sign reading "The Old Newspaper Building."

Downtown Poughkeepsie

4 out of top 10 points of interest in this area

If you're spending some time in Downtown Poughkeepsie, Bardavon 1869 Opera House and Mid-Hudson Civic Center are top sights worth seeing.

A suspension bridge over a river, surrounded by autumn foliage and urban buildings.

Red Oaks Mill

The river views, waterfalls, and breweries are just a few things travelers enjoy about Red Oaks Mill. If you want to experience more of the area, check out Locust Grove or Poughkeepsie Galleria.

Stay near popular Poughkeepsie attractions

A suspension bridge over a river with a forested hillside in the background.

Mid-Hudson Bridge

9.2/10 (235 reviews)

This engineering marvel spans the Hudson River with steel suspension elegance. Stroll the pedestrian path while experiencing "Bridge Music," a unique sound-art installation transforming the structure into an instrument.

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A steel bridge over a body of water with autumn foliage in the background.

Poughkeepsie Bridge

9.2/10 (244 reviews)

This former railroad bridge is now the world's longest elevated pedestrian walkway, offering panoramic Hudson River views. Stroll 212 feet above the water and discover the valley's beauty through changing seasons.

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A large, stately building with a symmetrical facade, stone detailing, and green shutters.

Eleanor Roosevelt National Historic Site

9.4/10 (111 reviews)

Explore the only National Historic Site dedicated to a First Lady at Eleanor Roosevelt's Val-Kill Cottage. Wander through her modest home where she shaped her humanitarian legacy after FDR's presidency.

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A lit bridge with a cross on top and a church with a steeple in the foreground.

Chance Theater

8.0/10 (70 reviews)

Enjoy a show at Chance Theater, a storied theater in Poughkeepsie. Amble around the area's riverfront or attend a sporting event.

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A large brick house with green shutters, surrounded by a grassy field and large trees.

Locust Grove

8.6/10 (63 reviews)

This 19th-century Italianate mansion was once home to telegraph inventor Samuel F.B. Morse. Explore original furnishings, stroll through formal gardens with century-old peonies, and hike trails with Hudson River views.

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Mid-Hudson Civic Center

8.4/10 (79 reviews)

This versatile venue hosts everything from concerts to trade shows in the heart of the Mid-Hudson Valley. Arrive early to secure parking and consider exploring downtown Poughkeepsie's dining options before your event.

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Bardavon 1869 Opera House

9.2/10 (18 reviews)

The Bardavon 1869 Opera House, NY State's oldest continuously operating theater, preserves 19th-century charm. Experience world-class performances in this intimate historic venue where heritage meets contemporary artistry.

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McCann Ice Arena

2.0/10 (1 review)

McCann Ice Arena offers year-round skating programs for all skill levels in a well-maintained facility. Create memories gliding across the ice or watch hockey games in this community sports hub.

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Poughkeepsie Hotel Deals

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

Fully refundableReserve now, pay when you stay

$94 nightly

$109 total

Nov 9 - Nov 10

Total with taxes and fees

9/10 Wonderful! (1,112 reviews)

"Guest room was designed well. Very clean. Comfortable bed. Great shower, strong pressure, like a massage. Breakfast was excellent , fresh and hot. Will be back"

Reviewed on Oct 10, 2026

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

Fully refundable

$87 nightly

$101 total

Nov 8 - Nov 9

Total with taxes and fees

The Heartwood

165 College Avenue Poughkeepsie NY

Fully refundableReserve now, pay when you stay

$169 nightly

$196 total

Nov 2 - Nov 3

Total with taxes and fees

See all 2,543 properties in Poughkeepsie

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Poughkeepsie Vacation Packages

Things to do in and around Poughkeepsie

Poughkeepsie offers a delightful mix of outdoor and family-friendly activities perfect for an adventure-filled vacation. Enjoy holiday events and festivals, explore nearby attractions, and unwind in beautiful picnic areas. The city also boasts a vibrant shopping scene and rich cultural experiences, making it an ideal destination for tourists seeking both recreation and relaxation.

Shopping

The Poughkeepsie Galleria, located 6 miles away, offers a vibrant shopping experience with various stores and entertainment options. If you're up for a drive, visit the Hudson Valley Mall, 18 miles away, for even more shopping and family-friendly activities. The Stormville Airport Antique Show & Flea Market, 13 miles away, is perfect for unique finds.

Recreation

At the Overlook Drive-In Theater, enjoy a nostalgic movie experience under the stars with family-friendly films that evoke a sense of romance and entertainment. For golf enthusiasts, Casperkill Golf Club offers a scenic outdoor setting to perfect your swing while soaking in the fresh air.

Adventure

Experience thrills at SplashDown Beach, an exciting waterpark located 11 miles from Poughkeepsie, perfect for family fun. For arcade enthusiasts, Fun Central offers adventure vibes 7 miles away. Enjoy outdoor camping and adventure at North Landing Beach, situated 9 miles from Poughkeepsie.

Nightlife

Poughkeepsie's nightlife offers a vibrant mix of bars and music venues. Check out The Chance Theater for live shows, or unwind at The Hairy Lemon for a cozy pub atmosphere. For a fun dance scene, visit The Poughkeepsie Grind, where you can enjoy great drinks and local DJs.

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

Find the best attractions in and around Poughkeepsie

Poughkeepsie, New York, offers a perfect blend of outdoor adventures and family-friendly activities, making it an ideal vacation spot. Visitors can explore local attractions like the Poughkeepsie Galleria, the historic Poughkeepsie Bridge, and the scenic waterfront. Whether you're seeking cultural experiences or thrilling adventures, this charming city has something for everyone to enjoy.

Vassar College: Experience the vibrant atmosphere of this modern college, known for its stunning architecture and beautiful campus. Take a stroll through its gardens, admire the art galleries, and soak in the intellectual energy that radiates from this prestigious institution.
Culinary Institute of America: Delve into the world of culinary arts at this historic college, located just 3 miles away. Enjoy exquisite dining experiences at its restaurants and witness future chefs honing their skills in a rich cultural setting that celebrates food and creativity.
Walkway Over the Hudson State Historic Park: Enjoy breathtaking views from this historic bridge, just 1 mile away. This elevated park offers scenic walking and biking trails, providing a unique opportunity to appreciate the majestic Hudson River and its surroundings.

Best time to go to Poughkeepsie

The best time to visit Poughkeepsie is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	27.5°F (-2.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	29.3°F (-1.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
April	48.4°F (9.1°C)	Light Rain	Mostly Sunny	Average	Average
May	59.4°F (15.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Average	Average
July	73.8°F (23.2°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	71.8°F (22.1°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	64.6°F (18.1°C)	Light Rain	Mostly Sunny	Average	Average
October	53.6°F (12.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
November	41.5°F (5.3°C)	Light Rain	Mostly Sunny	Average	Average
December	33.4°F (0.8°C)	Light Rain	Mostly Sunny	Average	Average

Tips to save on your trip to Poughkeepsie

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Poughkeepsie.
Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Poughkeepsie.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Poughkeepsie Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Stewart Intl. Airport (SWF)
Population	30,400
Max Temp Winter	35ºF
Max Temp Summer	80ºF
Top Sights	SplashDown Beach, Chance Theater and James Baird State Park

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Frequently asked questions

What types of vacation packages are available in Poughkeepsie?

Poughkeepsie, an outdoor and nature destination known for family-friendly attractions, offers vacation packages tailored to several travel styles:

Budget package: Quality Inn Poughkeepsie: offers a more affordable stay, with rooms around $150 per night, and includes free breakfast and an indoor pool.
Breakfast-included package: Homewood Suites by Hilton Poughkeepsie: rated 8.9 out of 10 by travelers, this hotel provides free breakfast and kitchenettes, making it convenient for longer stays.
Pet-friendly package: The Heartwood: a 3.5-star property rated 9.5 out of 10 by travelers, welcomes pets and offers a restaurant and bar/lounge.
Family package: Hampton Inn & Suites Poughkeepsie: rated 8.7 out of 10 by travelers, features family rooms and an indoor pool, providing comfort for those traveling with children.
Parking-included package: DoubleTree by Hilton Poughkeepsie Convention Center: a 4-star hotel rated 8 out of 10 by travelers, is praised for its great parking facilities, along with a restaurant and free breakfast.

How can I save money on a Poughkeepsie vacation package?

When you bundle, you can save up to 30%*. To save money on a Poughkeepsie package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

How much does a Poughkeepsie vacation package cost?

A Poughkeepsie vacation package typically costs around $800 per adult for a weekend trip. Lower-priced options start around $450 per adult, while premium packages can reach up to $1,650.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How do I find cheap Poughkeepsie vacation package deals?

The cheapest Poughkeepsie vacation package deals can be as low as around $370 per adult for weekend trips. Separately, April typically has the lowest average monthly prices, around $670 per adult, for a 3-day trip, while August follows at around $1,040 per adult, for a 4-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — nearly all Poughkeepsie packages include some savings versus booking separately, typically around $30 per adult. Longer, week-long trips can save even more, often around $50 per adult. Browse cheap vacation packages in Poughkeepsie on Expedia for current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

What is the best time to go to Poughkeepsie?

The best time to go for a Poughkeepsie vacation package is during its peak booking months of April, August, and November. April stands out as a particularly good option, as it is also typically the most affordable month for packages, making it a popular choice for value-conscious travelers.

What's included in a Poughkeepsie vacation package?

A Poughkeepsie vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Many hotels in Poughkeepsie offer free breakfast, providing a convenient start to your day. Some properties also provide airport shuttle services, which can be helpful for transfers from airports like John F. Kennedy International Airport (JFK).Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

What's the best vacation package for Poughkeepsie?

Families can build a Poughkeepsie vacation package around a stay at Hampton Inn & Suites Poughkeepsie, rated 8.7 out of 10 by travelers. This hotel offers family rooms and an indoor pool, making it a comfortable base, with travelers often praising the welcoming staff and good value for money in the rooms.For couples, The Heartwood, a 3.5-star property rated 9.5 out of 10, provides a thoughtful stay with its bar/lounge and restaurant, with guests highlighting the beautiful location and thoughtful rooms.Travelers seeking a budget-friendly Poughkeepsie vacation package might consider Quality Inn Poughkeepsie, which offers rooms around $150 per night. This hotel includes free breakfast and an indoor pool, with guests noting the nice rooms and clean pool.*Package availability and prices may change depending on dates and demand.

Is Poughkeepsie a good choice for a family vacation package?

Poughkeepsie is a good choice for family vacation packages, with some bookings being family trips. Hotels like Hampton Inn & Suites Poughkeepsie, rated 8.7 out of 10 by travelers, offer family rooms and indoor pools, providing comfortable stays for those traveling with children.For activities, families can visit Bowdoin Park, about 3 miles from central Poughkeepsie, which offers outdoor space for recreation. The Poughkeepsie Galleria, also about 3 miles from central Poughkeepsie, provides shopping and entertainment options.

What is the best time to book a Poughkeepsie vacation package?

Book your Poughkeepsie vacation package around 4 weeks in advance. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 2 and 8 weeks out.April, August, and November are the most popular months for Poughkeepsie packages, so booking earlier is advisable if you're traveling during those times.

What are the top things to do in Poughkeepsie?

A Poughkeepsie vacation offers a mix of historical sites, scenic outdoor experiences, and cultural attractions:Browse and book things to do in Poughkeepsie on Expedia.

How many days do you need for a Poughkeepsie vacation?

Most Poughkeepsie vacation packages last around 3 days, making it ideal for a weekend getaway. This duration allows travelers to experience key attractions like the Walkway Over the Hudson State Historic Park, the Franklin D. Roosevelt Presidential Library and Museum, and the Culinary Institute of America. While most travelers opt for weekend trips, nearly a third choose week-long trips to explore the region more deeply.

Is Poughkeepsie a good destination for a weekend vacation?

Poughkeepsie is an excellent choice for a weekend vacation package. Most travelers choose weekend trips for their Poughkeepsie vacation, having ample time to explore key attractions. A 1-to-3-day trip allows you to visit the Walkway Over the Hudson State Historic Park, explore the Culinary Institute of America, and delve into history at the Franklin D. Roosevelt Presidential Library and Museum.

Do you need to rent a car in Poughkeepsie, or is public transport enough?

For Poughkeepsie vacation packages with flights, a rental car generally offers the most flexibility to explore the wider Hudson Valley region. The nearest major airports include John F. Kennedy International Airport (JFK) and Newark Liberty International Airport (EWR).Within Poughkeepsie, Dutchess County Public Transit provides local bus service, with a main hub at Main and Market streets, near the Mid-Hudson Civic Center. For regional travel, Metro-North Railroad offers commuter rail service to New York City, and Amtrak also serves the Poughkeepsie station. However, given Poughkeepsie's character as an outdoor and nature destination outside the city, a car is beneficial for reaching attractions like Walkway Over the Hudson State Historic Park and other natural sites that may be spread out.

Are Poughkeepsie vacation package hotels conveniently located?

Poughkeepsie vacation package hotels are generally well-located, offering options both close to the center and slightly further out.The Heartwood is about 2 miles from central Poughkeepsie, while Homewood Suites by Hilton Poughkeepsie is about 3 miles away. For those preferring to be a bit further out, Hyatt Place Poughkeepsie / Hudson Valley is about 5 miles from central Poughkeepsie. Staying closer to central Poughkeepsie offers easier access to downtown attractions, while properties a bit further out provide convenient access to major routes and other area sights.

Can I change or cancel my Poughkeepsie vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Poughkeepsie vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Poughkeepsie vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Poughkeepsie vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Poughkeepsie?

To find last-minute vacation packages to Poughkeepsie, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Poughkeepsie vacation packages?

Free cancellation on a Poughkeepsie vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Poughkeepsie vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Poughkeepsie getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Poughkeepsie vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Poughkeepsie Vacations from $945

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Poughkeepsie Vacation

The Latest Poughkeepsie vacation packages

Modern Comfort in the Heart of NYC

Luxury NY Home 3BR with Easy Parking

Luxury NY Home with Free Parking

Modern Luxury Home w GameRoom & Parking

Luxury NYC Home Game Room Free Parking

Where to stay in Poughkeepsie

Arlington

Poughkeepsie Waterfront

Crown Heights

Downtown Poughkeepsie

Red Oaks Mill

Stay near popular Poughkeepsie attractions

Mid-Hudson Bridge

Poughkeepsie Bridge

Eleanor Roosevelt National Historic Site

Chance Theater

Locust Grove

Mid-Hudson Civic Center

Bardavon 1869 Opera House

McCann Ice Arena

Poughkeepsie Hotel Deals

Hyatt Place Poughkeepsie / Hudson Valley

Holiday Inn Express Poughkeepsie by IHG

The Heartwood

Find the Best Poughkeepsie Vacation Packages

Things to do in and around Poughkeepsie

Find the best attractions in and around Poughkeepsie

Best time to go to Poughkeepsie

Tips to save on your trip to Poughkeepsie

Poughkeepsie Essential Information

More vacations you might like

Frequently asked questions

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