Woodstock 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 Woodstock

Price found within the past 48 hours. Click for updated prices.
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $2,506, price is now CA $1,520 per person
CA $1,520
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (201 reviews)
I did not have breakfast, but I heard the breakfast. There is amazing. The bar was awesome. Great selection.!

Reviewed on Apr 4, 2026

42 Hotel

42 Hotel

3.5 out of 5
Price was CA $3,547, price is now CA $1,885 per person
CA $1,885
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (847 reviews)
This Hotel is so cool. The staff is beyond helpful and friendly. We cant wait to come back next year.

Reviewed on Apr 15, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $7,147, price is now CA $3,975 per person
CA $3,975
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

Seven Beach Lane

Seven Beach Lane

2 out of 5
Price was CA $4,830, price is now CA $2,804 per person
CA $2,804
per person
May 27 - Jun 1
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
10/10 Exceptional! (7 reviews)
Courteous and friendly staff

Reviewed on Nov 4, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $2,812, price is now CA $1,738 per person
CA $1,738
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Everything is great about this Hotel.

Reviewed on Apr 9, 2026

Where to stay in Woodstock

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

Woodstock 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 $185 per night from Apr 26 to Apr 27
CA $185
CA $280 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,401 reviews)
Easy check in

Reviewed on Apr 19, 2026

Hotel Edison Times Square
DoubleTree by Hilton New York Downtown

DoubleTree by Hilton New York Downtown

4 out of 5
8 Stone St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Apr 26 to Apr 27
CA $166
CA $196 total
Apr 26 - Apr 27
includes taxes & fees
8.4/10 Very Good! (3,683 reviews)
Great location. Friendly employees

Reviewed on Apr 19, 2026

DoubleTree by Hilton New York Downtown
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 $212 per night from Apr 26 to Apr 27
CA $212
CA $303 total
Apr 26 - Apr 27
includes taxes & fees
7.4/10 Good! (7,589 reviews)
Overall a great stay with family. Elevators fast and staff friendly. Good deal for the location. Only negative I had was we arrived early and had to wait literally over an hour in line just to drop our bags at baggage check. And the. To retrieve your bags later you had to wait as well but fortunately ...

Reviewed on Apr 19, 2026

Sheraton New York Times Square Hotel
See all 13,322 properties in Woodstock
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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Woodstock vacation package cost?
Get your credit card ready, because a trip to Woodstock starts from an enticing CA $1,520. When you combine your hotels, flights and car rentals into a vacation package, you'll pick up great deals.
How do I get a cheap travel package to Woodstock?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you cash too. A Woodstock vacation package makes it a breeze to arrange the perfect trip. With more than 550 airlines throughout the world to choose from, finding flights that fit your busy schedule won't be hard. In addition to that, we've got over 1,000,000 properties globally to take your pick of. Talk about choice! No matter who you are, Expedia brings the world within your reach.
Where should I stay in Woodstock?
Consider staying close to Yankee Stadium, one of this neighborhood's top attractions. It's the perfect place if you're looking to capture some great travel photos.
What are the top hotels in Woodstock?
Opera House Hotel is one of Woodstock's top hotels. Lock in a room here and you'll rest easy knowing you're in excellent hands.
How far in advance should I book my Woodstock vacation?
While prices change from time to time, we generally recommend booking your vacation as soon as possible. Many international airfares are available on Expedia up to a year in advance. If circumstances have left you booking last minute, you may still get lucky. Cheap tickets to Woodstock sometimes appear just weeks before departure.
What does an Expedia Woodstock travel package include?
Much of that is up to you. You can select from a variety of Woodstock bundles, such as a flight, rental car and hotel. You can also book a hotel and a flight, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your perfect Woodstock trip looks like, get set to save!
What should I know before booking a Woodstock travel package?
You'll save big with an Expedia travel package. Bundle your flights, rental cars and hotels and score fabulous discounts. You're not restricted to hotels, though. We have beachside condos, creek-side mountain cabins and just about everything in between!
Can I choose my airline with a Woodstock Expedia vacation package?
Yes, you're in control. We offer more than 550 airlines around the world, so you can design your Woodstock getaway according to your style and budget.
If I'm not able to travel, can I cancel my Woodstock vacation package?
Because we know life can be unpredictable, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it without penalty. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.

Discover the most popular places to visit in Woodstock

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.