Oakwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $2,406, price is now CA $1,468 per person
CA $1,468
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (2,926 reviews)
Centrally located. Room clean. Hotel quiet and staff is pleasant.

Reviewed on Apr 21, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $7,138, price is now CA $3,740 per person
CA $3,740
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
Price was CA $6,633, price is now CA $3,693 per person
CA $3,693
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,004 reviews)
Awesome all the way round

Reviewed on Apr 19, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,785, price is now CA $1,607 per person
CA $1,607
per person
Jun 7 - Jun 9
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Don’t ever think you will check in prior to the late 4pm check in. No matter what. Not even 5 minutes.

Reviewed on Apr 17, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $2,802, price is now CA $1,665 per person
CA $1,665
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,162 reviews)
i found female hair on bed on my checked in

Reviewed on Apr 22, 2026

Where to stay in Oakwood

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

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

Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
228 W 47th St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Apr 26 to Apr 27
CA $173
CA $266 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,427 reviews)
Staff is very accommodating and made my son’s 18th birthday on Broadway super special. Upgraded us to a suite for free! And managed to get us early check in during a busy vacation week. 5th stay at the Edison and will never stay anywhere else in the city!

Reviewed on Apr 22, 2026

Hotel Edison Times Square
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 $239 per night from Apr 26 to Apr 27
CA $239
CA $342 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (6,714 reviews)
Room smelled of mildew and bathroom wasn’t cleaned when we got there. Asked to switch rooms and it was better.

Reviewed on Apr 22, 2026

Hyatt Grand Central New York
NEW YORKER BY LOTTE HOTELS

NEW YORKER BY LOTTE HOTELS

4 out of 5
481 Eighth Ave. New York NY
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Apr 26 to Apr 27
CA $163
CA $254 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (6,639 reviews)
Staff is always friendly. Property a little dated but great location.

Reviewed on Apr 21, 2026

NEW YORKER BY LOTTE HOTELS
See all 12,099 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

Frequently asked questions

How much does an Oakwood vacation package cost?
Starting from a low CA $1,468, 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.

Discover the most popular places to visit in Oakwood

Times Square

Times Square

4.5/5(3,520 reviews)

New York’s infamous neon wonderland is hustle and bustle at its best, and an essential stop for all tourists.

Times Square
Central Park

Central Park

4.5/5(2,961 reviews)

Offering blissful respite from Manhattan’s concrete jungle, this is the perfect spot to rest weary feet or enjoy a picnic.

Central Park
view from top on Madison Square Garden and Empire State Building. Night Lights

Madison Square Garden

4.5/5(447 reviews)

Whether you’re performing here, watching your favorite sports team or entertainer or touring the venue, you’re in for an exciting event.

Madison Square Garden

Things to do

SUMMIT One Vanderbilt Experience Tickets

SUMMIT One Vanderbilt Experience Tickets

CA $66
per adult
94% of travellers recommend
SUMMIT One Vanderbilt Experience Tickets
Go City: New York Explorer Pass - Entry to 2 to 10 Top Attractions

New York Explorer Pass: Visit 2-10 Attractions and Save Up to 50 Percent

CA $117
per adult
84% of travellers recommend
New York Explorer Pass: Visit 2-10 Attractions and Save Up to 50 Percent
Empire State Building Observatory Tickets - General Admission & Express

Empire State Building Observation Deck & Museum Ticket

CA $66
per adult
90% of travellers recommend
Empire State Building Observation Deck & Museum 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.