Pine Orchard 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*

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    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 Pine Orchard

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 $1,672, price is now CA $1,015 per person
CA $1,015
per person
Jan 23 - Jan 30
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $3,781, price is now CA $1,974 per person
CA $1,974
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,226, price is now CA $1,249 per person
CA $1,249
per person
Jan 7 - Jan 10
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $3,333, price is now CA $2,079 per person
CA $2,079
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (673 reviews)
Excellent stay

Reviewed on Oct 26, 2026

The Mark

The Mark

5 out of 5
Manhattan
Price was CA $4,235, price is now CA $2,649 per person
CA $2,649
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (723 reviews)
Fire alarm went off three times in middle of the night and no apology or refund.

Reviewed on Nov 8, 2026

Pine Orchard Hotel Deals

Gorgeous 3BR Beach House with Private Beach Access.

Gorgeous 3BR Beach House with Private Beach Access.

Branford CT
9.8/10 Exceptional! (86 reviews)
"Tidy and cute, with very professional/responsive hosts!"

Reviewed on Oct 19, 2026

Get rates
Gorgeous 3BR Beach House with Private Beach Access.
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
The price is CA $172 per night from Nov 25 to Nov 26
CA $172
CA $198 total
Nov 25 - Nov 26
includes taxes & fees
9.2/10 Wonderful! (2,414 reviews)
"This is my go-to hotel when I travel to CT. Excellent rooms, great interior design, and a lobby that's also very amenable to working travelers. And the staff is amazing! I've never had a bad experience. Definitely recommend"

Reviewed on Nov 10, 2026

New Haven Hotel
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
The price is CA $155 per night from Nov 19 to Nov 20
CA $155
CA $178 total
Nov 19 - Nov 20
includes taxes & fees
Best Western Executive Hotel Of New Haven - West Haven
See all 1,005 properties in Pine Orchard
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 Pine Orchard vacation package cost?
Much less than you might think — from as low as CA $1,015, actually! By combining flights, hotels and car rentals into your own custom-built package, your trip to Pine Orchard is only clicks away.
How do I get a cheap travel package to Pine Orchard?
Just imagine all the fabulous things you could do in Pine Orchard with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your airfare and hotel bookings into a Pine Orchard vacation package. You have plenty of choice with Expedia too. In fact, you can select from more than 550 airlines and 1,000,000 hotel options around the world. Whether you're vacationing with the whole family or embarking on a solo adventure, organizing a getaway to Pine Orchard is better with a package.
Where should I stay in Pine Orchard?
A trip to Pine Orchard isn't complete without paying a visit to Stony Creek Brewery, Double Beach and Orchard Hill Plaza Shopping Center. Stay near these top attractions and make sightseeing easy.
What are the top hotels in Pine Orchard?
Get your trip off to a good start by locking in a room at Charming Coastal Retreat Steps From The Beach. It's one of most popular properties in Pine Orchard. Another top option is Ennis Cottage - A Holiday By The Sea.
How far in advance should I book my Pine Orchard vacation?
It's hard to pick the perfect time for airfares, but we generally suggest the earlier, the better. Plenty of international flights on Expedia become available up to a year in advance. If you're booking late, don't stress. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Pine Orchard travel package include?
It's up to you! You can choose from a variety of Pine Orchard packages, such as a hotel, flight and rental car. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like activities and tours. Whatever your dream Pine Orchard escape looks like, get ready to save!
What should I know before booking a Pine Orchard travel package?
A travel package can be easier on the credit card than individually booking everything you need for your trip. For example, combine your hotels, flights and rental cars and save a pretty penny. Whatever type of vacation you have in mind, you'll find a package within your budget.
If I'm not able to travel, can I cancel my Pine Orchard vacation package?
Certainly, and we'll help you every step of the way. You may be able to amend or cancel your Pine Orchard vacation package for free if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, browse our Customer Service Portal for further information.

Things to do

New Haven's Ghost Walk

New Haven's Ghost Walk

CA $37
per adult
New Haven's Ghost Walk
See all activities in Branford
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.