Upper West Side Vacation Packages

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Top Holiday Package Deals in Upper West Side

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

Eurostars Wall Street

4 out of 5
Manhattan
Price was CA $1,833, price is now CA $1,106 per person
CA $1,106
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8/10 Very good! (1,000 reviews)
The best part of this hotel is the proximity and the size of the room. Hotel staff really hands-off, no amenities. Hotel very out dated and kind of dingy looking.

Reviewed on Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,502, price is now CA $1,381 per person
CA $1,381
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $2,413, price is now CA $1,539 per person
CA $1,539
per person
Jan 13 - Jan 20
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Clean and comfortable

Reviewed on Nov 2, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Price was CA $4,525, price is now CA $2,895 per person
CA $2,895
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

Where to stay in Upper West Side

Find the best Upper West Side areas and neighborhoods for the activities you enjoy most. Learn more about Upper West Side
A busy urban square with tall buildings, American flags, and a crowd of people.

Manhattan

8 out of top 10 points of interest in this area

Densely populated and culturally rich, this area boasts iconic attractions like Times Square, Central Park, and Grand Central Terminal. Explore diverse neighborhoods, such as bustling Chinatown and vibrant Koreatown, while enjoying world-class shopping on Fifth Avenue.

Find hotels in Manhattan

Upper West Side Hotel Deals

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
215 W 94th St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $223 total
Nov 23 - Nov 24
includes taxes & fees
Night Hotel Broadway
Empire Hotel

Empire Hotel

4 out of 5
44 W 63rd St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Nov 22 to Nov 23
CA $173
CA $235 total
Nov 22 - Nov 23
includes taxes & fees
7.6/10 Good! (7,244 reviews)
"Very vintage which was really nice. The bathroom did not have an exhaust fan, nor did the windows open. So after a shower, all of the moisture gets trapped in the room. Made the carpet have a damp feel to it. Lighting was also challenge. Other than that, everything else was great."

Reviewed on Nov 6, 2026

Empire Hotel
Hotel Belleclaire Central Park, a Small Luxury Hotel

Hotel Belleclaire Central Park, a Small Luxury Hotel

4 out of 5
2175 Broadway New York NY
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Nov 22 to Nov 23
CA $248
CA $344 total
Nov 22 - Nov 23
includes taxes & fees
Hotel Belleclaire Central Park, a Small Luxury Hotel
See all 12,404 properties in Upper West Side
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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Frequently asked questions

How much does an Upper West Side vacation package cost?
We make it simple to explore the world, with Upper West Side packages starting from as little as CA $1,106. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate escape, why not add a couple of tours and experiences to your itinerary?
How do I get a cheap travel package to Upper West Side?
Combining your flight and hotel with Expedia won't just save you time — it'll save you a pretty penny too. An Upper West Side vacation package makes it a cinch to arrange the ideal trip. With more than 550 airlines around the world to select from, finding convenient flights that fit your busy schedule won't be hard. Not only that, we have over 1,000,000 hotel options globally to choose from. Talk about choice! No matter who you are, Expedia puts more of the world within your reach.
Where should I stay in Upper West Side?
A getaway to Upper West Side isn't complete without seeing Jacob K. Javits Convention Center, Metropolitan Opera House and Riverside Park. Spend your evenings close to these top attractions and make sightseeing a breeze.
What are the top hotels in Upper West Side?
Get your trip off to a flying start by booking a room at Spectacular Central Park Home In The Heart Of Upper West Side. It's one of most popular hotels in Upper West Side. Another cozy option is Central Park Stunning Duplex.
How far in advance should I book my Upper West Side vacation?
It's hard to pick the perfect time for airfares, but we usually say the earlier, the better. Most international flights on Expedia become available up to 12 months in advance. If you're booking last minute, fear not. Discounted prices appear from time to time just weeks before departure dates.
What does an Expedia Upper West Side travel package include?
Expedia has everything you need to arrange your Upper West Side trip, but what goes into your package is your call. Select from a combination of rental cars, flights and hotels. Looking for some tours or experiences to keep you busy? Once you've made your booking, you can add them on too. No matter your budget or style, there's a deal to match your needs.
What should I know before booking an Upper West Side travel package?
Bundling your bookings into an Upper West Side vacation package is the most convenient way to organize your trip. Not only that, you'll get great discounts when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with an Upper West Side Expedia vacation package?
Yes, and with over 550 airlines to choose from across the globe, you have loads of choice. Search the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Upper West Side vacation package?
It is possible to cancel your Upper West Side booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Stay near popular Upper West Side attractions

A public square with a fountain, a large building with columns, and a Lincoln Center entrance.
Photo by Lincoln Centre for the Performing Arts/Iñaki Vinaixa
Open Photo by Lincoln Centre for the Performing Arts/Iñaki Vinaixa

Lincoln Center

9.4/10 (1,642 reviews)
See some of the world’s greatest performing arts events in one of the most culturally rich cities on the planet in this large architecturally impressive complex.
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Things to do

Tyrannosaurs rex skeleton in the American Museum of Natural History in New York

American Museum of Natural History Tickets

CA $50
per adult
82% of travellers recommend
American Museum of Natural History Tickets
Edge Immersive Observation Deck Ticket

Edge Immersive Observation Deck Ticket

CA $61
per adult
94% of travellers recommend
Edge Immersive Observation Deck Ticket
NYC Pub Crawl & Rooftop Clubbing Experience

NYC Pub Crawl & Rooftop Clubbing Experience

CA $35
per adult
NYC Pub Crawl & Rooftop Clubbing Experience
See all activities in New York

Explore a world of travel with Expedia

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