Oakwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Oakwood

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,587, price is now CA $991 per person
CA $991
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The best hotel near Times Square

Reviewed on Oct 27, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,969, price is now CA $1,234 per person
CA $1,234
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,714 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,176, price is now CA $1,383 per person
CA $1,383
per person
Dec 9 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
Very nice and clean hotel. The staff were friendly.

Reviewed on Oct 26, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,968, price is now CA $2,615 per person
CA $2,615
per person
Jan 11 - Jan 15
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!

Reviewed on Oct 19, 2026

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,147, price is now CA $1,435 per person
CA $1,435
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,823 reviews)
Great location and very spacious room.

Reviewed on Oct 26, 2026

Where to stay in Oakwood

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

Oakwood Hotel Deals

ROW NYC

ROW NYC

4 out of 5
700 8th Avenue New York NY
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Nov 15 to Nov 16
CA $252
CA $359 total
Nov 15 - Nov 16
includes taxes & fees
8/10 Very good! (2,728 reviews)
"El servicio del cuarto muy bueno la camarera siempre estuvo pendiente de todo, un ascensor parece del terror deberían repararlo, no estoy de acuerdo con q bloqueen 500 cuando realmente te dicen q solo son 190 o menos."

Reviewed on Oct 27, 2026

ROW NYC
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
455 Madison Ave New York NY
9/10 Wonderful! (2,329 reviews)
"Very attentive cleaning services, and overall the staffers were a great help. The location was very desirable to us and we would stay again!"

Reviewed on Oct 26, 2026

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Lotte New York Palace
Pod Times Square

Pod Times Square

3 out of 5
400 W 42nd Street New York NY
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Nov 22 to Nov 23
CA $150
CA $219 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (6,229 reviews)
"Great location! The staff were very friendly and professional. No dining although it is advertised but the bar is very nice and has a good selection. The room was small but okay with me as I have a tendency to "spread out". The bathroom was very modern and clean. I will definitely stay again!"

Reviewed on Oct 27, 2026

Pod Times Square
See all 11,283 properties in Oakwood
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
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Beach Vacations
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Frequently asked questions

How much does an Oakwood vacation package cost?
Starting from a low CA $991, a vacation package is your ticket to low-cost travel. Put together your Oakwood adventure by selecting from our huge range of flights, hotels and rental cars.
How do I get a cheap travel package to Oakwood?
Track down flights that fit your busy schedule, add a hotel room to your booking and watch the savings grow with an Oakwood vacation package. It's as easy as that! From flights and hotels to tours and rental cars, Expedia is where your cheap vacation begins. And with more than 550 air carriers and 1,000,000 hotels around the world to pick from, you won't be short of choice.
Where should I stay in Oakwood?
Take the hassle out of sightseeing by staying in a hotel close to Oakwood's biggest attractions. Brooklyn Bridge and Yankee Stadium are two of the best in this neighborhood.
How far in advance should I book my Oakwood vacation?
Travelers are generally able to browse international flights on Expedia within 12 months of departure. Booking at the last minute? With a stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Oakwood travel package include?
Car rentals, flights and hotels — we connect you to the very best bargains. All you'll have to do is select your ideal combination. Once you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it easy to craft an awesome Oakwood trip.
What should I know before booking an Oakwood travel package?
Bundling your bookings into an Oakwood vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with an Oakwood Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Oakwood vacation package?
Whether it's your flight or hotel, you can cancel and rebook it. Locked in your Oakwood vacation package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may incur a charge from your hotel, airline or car rental company. For more information, check out our Customer Service Portal. We'll help you each step of the way.

Stay near popular Oakwood attractions

Oakwood Beach

Why not spend a lazy afternoon at Oakwood Beach during your trip to Staten Island? Stroll along the waterfront or experience the museums in this family-friendly area.
See properties

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: Museum of Modern Art

NYC: Museum of Modern Art (MoMA) Entry Ticket

CA $42
per adult
96% of travellers recommend
NYC: Museum of Modern Art (MoMA) Entry Ticket
See all activities in New York
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.