Upper Montclair Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Upper Montclair

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,286, price is now CA $834 per person
CA $834
per person
Apr 18 - Apr 21
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (6,546 reviews)
Yes, room was clean and renovated with private updated bathroom. Quest service was very polite and courteous. I will most definitely book there again.

Reviewed on Feb 8, 2026

The George

The George

4 out of 5
Price was CA $2,904, price is now CA $1,744 per person
CA $1,744
per person
Apr 16 - Apr 23
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (444 reviews)
The place is beautiful. Clean and comfortable. A little chilly where breakfast was served but it was unusually very cold outside. Love the library to relax Def highly recommend

Reviewed on Feb 2, 2026

Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was CA $2,387, price is now CA $1,441 per person
CA $1,441
per person
Mar 14 - Mar 21
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,678 reviews)
Hip boutique hotel with an industrial cozy vibe. Rooms are sumple but have everything you need. The libby bar and cafe are nice. Attached to Serafina restaurant. Great lication overall and parking across the street.

Reviewed on Feb 6, 2026

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $3,189, price is now CA $2,049 per person
CA $2,049
per person
Apr 26 - May 2
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,565 reviews)
We loved to stay here but hotel wifi is too mush slow and some the telephone doesn’t work.all other the staff was so good and nice rooms.

Reviewed on Feb 8, 2026

Madison Hotel

Madison Hotel

4 out of 5
Price was CA $2,365, price is now CA $1,558 per person
CA $1,558
per person
Apr 16 - Apr 23
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
We ate at Rods, connected to the hotel5 stars for service and food!!!

Reviewed on Jan 22, 2026

Upper Montclair 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 $176 per night from Feb 22 to Feb 23
CA $176
CA $261 total
Feb 22 - Feb 23
includes taxes & fees
7.2/10 Good! (6,739 reviews)
Great stay with my kids! Our flight arrived early, and even though check-in wasn’t until 4 PM, the front desk was able to accommodate us with early check-in, which we really appreciated. The room and hotel were clean and well maintained. We also used the luggage storage service for a small fee after ...

Reviewed on Feb 7, 2026

Sheraton New York Times Square Hotel
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 $208 per night from Feb 21 to Feb 22
CA $208
CA $306 total
Feb 21 - Feb 22
includes taxes & fees
8.2/10 Very Good! (6,447 reviews)
Everything and everyone was great!

Reviewed on Feb 4, 2026

Hyatt Grand Central New York
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
145 W 44th St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Feb 10 to Feb 11
CA $171
CA $248 total
Feb 10 - Feb 11
includes taxes & fees
7.6/10 Good! (6,540 reviews)
The room was a little dated but everything in it that we needed, very comfortable beds, toiletries, hairdryer, tv and housekeeping every day. Unfortunately did not meet the housekeeping staff as we were out every day. Receptionist and concierge were excellent.

Reviewed on Feb 7, 2026

Millennium Hotel Broadway Times Square
See all 12,301 properties in Upper Montclair
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.
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Frequently asked questions

How much does an Upper Montclair vacation package cost?
The most affordable Upper Montclair vacation package is CA $834, so the trip of your dreams can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to create a package that matches your traveling style.
How do I get a cheap travel package to Upper Montclair?
One word: bundle. Hotels, flights and rental cars — combine whatever you need into an Upper Montclair vacation package and save. Score even bigger bargains when you add extras such as activities or tours to your booking. But that's not the only good part. You have the flexibility to put together your trip your own way. We offer over 550 partner airlines and 1,000,000 properties throughout the world, so that everyone has a chance to travel and live out those vacation fantasies.
Where should I stay in Upper Montclair?
A vacation in Upper Montclair wouldn't be complete without checking out Wellmont Theatre, Montclair Art Museum and Van Vleck House & Gardens. Spend your evenings close to these sights and make sightseeing a breeze.
How far in advance should I book my Upper Montclair vacation?
It can be difficult to know exactly when the best time is to book your Upper Montclair vacation. But usually the earlier you book, the better the prices. In some cases, you can secure your flights and hotels up to 12 months prior to your departure date. If you're eager to escape on a last-minute getaway, no need to stress! There are unbeatable bargains advertised on Expedia every single day.
What does an Expedia Upper Montclair travel package include?
It comes down to what you're looking for. If you're traveling solo, you might decide to combine hotels and flights. Bringing the whole family to Upper Montclair? A travel package including rental cars, flights and hotels might suit you better. Expedia gives you the freedom to tailor-make your travel package.
What should I know before booking an Upper Montclair travel package?
Design deals that suit your budget with an Expedia package. Hotels, airfares, rental cars — we've got all of them. You'll save a tidy sum just for combining your bookings. Whether you're taking off on a ski adventure or venturing someplace warm, your ideal vacation is only a few clicks away.
Can I choose my airline with an Upper Montclair Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Simply select the airline you want and create your ideal Upper Montclair getaway.
If I'm not able to travel, can I cancel my Upper Montclair vacation package?
Whether it's your hotel or flight, you can cancel and rebook it. Locked in your Upper Montclair vacation package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may incur a fee from your airline, hotel or car rental company. For further information, look up our Customer Service Portal. We'll help you each step of the way.

Discover the most popular places to visit in Upper Montclair

Van Vleck House & Gardens featuring a garden

Van Vleck House & Gardens

Meander through these pretty gardens to appreciate the range of exotic specimens and attend a piano recital or art exhibit in the house.

Van Vleck House & Gardens

Things to do

American Dream: SEA LIFE New Jersey Aquarium

American Dream: SEA LIFE New Jersey Aquarium

CA $44
per traveller
88% of travellers recommend
American Dream: SEA LIFE New Jersey Aquarium
American Dream: LEGOLAND Discovery Center New Jersey

American Dream: LEGOLAND Discovery Center New Jersey

CA $44
per traveller
100% of travellers recommend
American Dream: LEGOLAND Discovery Center New Jersey
American Dream: Angry Birds Mini Golf Ticket

American Dream: Angry Birds Mini Golf Ticket

CA $29
per adult
American Dream: Angry Birds Mini Golf Ticket
See all activities in Montclair
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.