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*

  • 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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,592, price is now CA $994 per person
CA $994
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Extremely clean. Staff very courteous. One of the best dining areas for breakfast/dinner food service.

Reviewed on Feb 21, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,946, price is now CA $1,174 per person
CA $1,174
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
Great stay! Will be returning!

Reviewed on Feb 23, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $2,944, price is now CA $1,799 per person
CA $1,799
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Service at the hotel was fantastic!!! Beds are comfy, and bathrooms are very very nice!

Reviewed on Feb 21, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,211, price is now CA $1,390 per person
CA $1,390
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,790 reviews)
Friendly staff and room is very clean.

Reviewed on Feb 23, 2026

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Price was CA $5,813, price is now CA $3,791 per person
CA $3,791
per person
Mar 27 - Apr 1
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (60 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on Oct 10, 2025

Where to stay in Oakwood

Find the best Oakwood areas and neighborhoods for the activities you enjoy most. Learn more about Oakwood
Wall Street which includes heritage architecture, street scenes and a city

Manhattan

8 out of top 10 points of interest in this area
4.5/5(3,032 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

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave New York NY
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Mar 1 to Mar 2
CA $183
CA $270 total
Mar 1 - Mar 2
includes taxes & fees
7.4/10 Good! (6,988 reviews)
Staff was very friendly and helpful

Reviewed on Feb 23, 2026

Sheraton New York Times Square Hotel
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 $128 per night from Feb 24 to Feb 25
CA $128
CA $215 total
Feb 24 - Feb 25
includes taxes & fees
8.2/10 Very Good! (6,436 reviews)
Perfect location!

Reviewed on Feb 23, 2026

NEW YORKER BY LOTTE HOTELS
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 $184 per night from Feb 26 to Feb 27
CA $184
CA $278 total
Feb 26 - Feb 27
includes taxes & fees
8.2/10 Very Good! (6,510 reviews)
Very accommodating during huge snowstorm.

Reviewed on Feb 23, 2026

Hyatt Grand Central New York
See all 11,976 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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Frequently asked questions

How much does an Oakwood vacation package cost?
Starting from a low CA $994, 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 featuring a city, central business district and signage

Times Square

4.5/5(3,459 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 showing flowers, a park and a pond

Central Park

4.5/5(2,909 reviews)

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

Central Park
NewYork_MadisonSquareGarden_6291778_8

Madison Square Garden

4.5/5(443 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 $65
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 $121
per adult
84% of travellers recommend
New York Explorer Pass: Visit 2-10 Attractions and Save Up to 50 Percent
Edge Observation Deck at Hudson Yards

Edge Observation Deck at Hudson Yards

CA $53
per adult
100% of travellers recommend
Edge Observation Deck at Hudson Yards
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.