Oakwood Vacation Packages

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  • Better together

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

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

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Top Holiday Package Deals in Oakwood

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

Placemakr Wall Street

4 out of 5
Manhattan
Price was CA $1,430, price is now CA $872 per person
CA $872
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (944 reviews)
Very livable.

Reviewed on Jul 9, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $3,721, price is now CA $1,910 per person
CA $1,910
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.4/10 Good! (3,239 reviews)
The room was clean the air conditioning was perfect at 60 degrees and the heater (hubby is anemic)was perfect at H2. The front desk staff was courteous, polite and professional. The eateries in the area McDonald's, the Chinese Restaurant and the Pizzeria are over priced and the food was not that good. There is a deli on the corner of 93rd Street is reasonably priced and the sandwiches and salads were delicious. I can't comment on parking because we took a taxi and public transportation. Overall we had a good time and a nice experience.

Reviewed on Jul 9, 2026

The Wall Street Inn

The Wall Street Inn

3 out of 5
Manhattan
Price was CA $4,196, price is now CA $2,475 per person
CA $2,475
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
Lovely spot convenient to the activities we were doing. Very friendly and helpful stuff.

Reviewed on Jul 5, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,493, price is now CA $2,239 per person
CA $2,239
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,434, price is now CA $937 per person
CA $937
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
The place smelled from when you get in till inside the room. Like garbage and a mix of cigarettes and alcohol

Reviewed on Jul 10, 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
4.5/5(3,072 area reviews)

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 $273 per night from Aug 4 to Aug 5
CA $273
CA $384 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (276 reviews)
"Junior and Armanda were exceptionally helpful and accommodating! After a fiscal with parking, Junior was able to rectify the issue and offered additional support for my daughters and I! Extraordinary view of the city and security was always around. Breakfast was delicious and not like a full service, ..."

Reviewed on Jul 10, 2026

ROW NYC
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Jul 26 to Jul 27
CA $248
CA $355 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very good! (7,327 reviews)
"This hotel is the best! Clean, perfect location!"

Reviewed on Jul 10, 2026

Hyatt Grand Central New York
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 $282 per night from Jul 26 to Jul 27
CA $282
CA $361 total
Jul 26 - Jul 27
includes taxes & fees
7.6/10 Good! (6,966 reviews)
"The hotel is an amazing location, close to tons of attractions. Walking distance to so many places. Single bed room was smaller but totally worth it."

Reviewed on Jul 10, 2026

Empire Hotel
See all 12,062 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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Frequently asked questions

How much does an Oakwood vacation package cost?
Starting from a low CA $872, 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

American Dream: SEA LIFE New Jersey Aquarium

American Dream: SEA LIFE New Jersey Aquarium

CA $47
per traveller
88% of travellers recommend
American Dream: SEA LIFE New Jersey Aquarium
Tyrannosaurs rex skeleton in the American Museum of Natural History in New York

American Museum of Natural History Tickets

CA $53
per adult
82% of travellers recommend
American Museum of Natural History Tickets
Central Park Zoo Admission Ticket with 4D Theater Access

Central Park Zoo Admission Ticket with 4D Theater Access

CA $33
per adult
84% of travellers recommend
Central Park Zoo Admission Ticket with 4D Theater Access
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.