Montclair Colony Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in Montclair Colony

Price found within the past 48 hours. Click for updated prices.
The William Hotel Midtown, New York

The William Hotel Midtown, New York

Manhattan
Save 100% on your flight
CA $1,425
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.4/10 Exceptional! (232 reviews)
The staff are wonderful, helpful, and so kind!

Reviewed on Sep 20, 2026

Lotte New York Palace

Lotte New York Palace

Manhattan
Save 100% on your flight
CA $2,796
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,230 reviews)
Great location with helpful staff. Would stay here again.

Reviewed on Sep 20, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

Manhattan
Save 100% on your flight
CA $2,210
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (702 reviews)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
Save 100% on your flight
CA $1,702
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,950 reviews)
Had a great experience at Rui. The room was clean, staff were so friendly and helpful. Check in and out was fast and efficient. Had a wonderful experience.

Reviewed on Sep 20, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

Save 100% on your flight
CA $1,673
per person
Nov 21 - Nov 24
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Where to stay in Montclair Colony

Find the best Montclair Colony areas and neighborhoods for the activities you enjoy most. Learn more about Montclair Colony
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Historical Society and Mashomack Preserve, some noteworthy sights in the nearby area.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach might not have many top sights, but Greenport Carousel and Greenport Harbor Brewing Company are two attractions nearby that you can check out.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

Montclair Colony Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
CA $113
CA $129 total
Oct 8 - Oct 9
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
CA $251
CA $312 total
Oct 7 - Oct 8
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Beautiful setting . Dined at the restaurant food was good , service was excellent . The main dining room is lovely but loud and noisy. Also, the room was adequate however they don't even give you a complimentary bottle of water !"

Reviewed on Sep 20, 2026

Water's Edge Resort & Spa
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $167
CA $226 total
Oct 1 - Oct 2
includes taxes & fees
7.2/10 Good! (1,002 reviews)
"Updated motel, with a beachy feel. We booked the honeymoon suite to make use of the jetted tub, which has seen better days. Our room was in the back so it was quiet. The pool area was nice and we lounged in the sun for a while. The place is like a little hidden gem, no-frills, clean, and they make ..."

Reviewed on Sep 20, 2026

The Atlantic Hotel
See all 3,951 properties in Montclair Colony
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.

Frequently asked questions

How much does a Montclair Colony vacation package cost?
From just CA $1,425, you can tailor make your Montclair Colony package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Montclair Colony?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you money too. A Montclair Colony vacation package makes it a breeze to create your ideal trip. With more than 550 airlines all over the world to select from, finding convenient flights that suit your busy schedule won't be a challenge. In addition to that, we have over 1,000,000 hotels globally to select from. Now that's what we call choice. No matter who you are, Expedia brings the world within your reach.
Where should I stay in Montclair Colony?
With so much to do in Montclair Colony, it'd be handy for you to stay close to its attractions. Shell Beach, Shelter Island Historical Society and Wades Beach are some interesting ones to put on your itinerary.
How far in advance should I book my Montclair Colony vacation?
Travelers can normally look up international flights on Expedia up to 12 months prior to departure. Booking last minute? With a little bit of luck, it's still possible to nab an affordable ticket just weeks before your journey.
What does an Expedia Montclair Colony travel package include?
That depends on what you're looking for. If you're traveling by yourself, you might decide to bundle flights and hotels. Taking the whole family to Montclair Colony? A travel package that includes hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to tailor-make your travel package.
What should I know before booking a Montclair Colony travel package?
A package can be more affordable than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and land a great deal. Whatever your vacation goals are, you'll find a package that's right for you.
Can I choose my airline with a Montclair Colony Expedia vacation package?
Yes, and with over 550 airlines to choose from throughout the world, you're spoiled for choice. Browse the available options and find out which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Montclair Colony vacation package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Montclair Colony vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings older than that, you may incur a fee from your hotel, airline or car rental company. For more details, head to our Customer Service Portal. We're here to help you every step of the way.

Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

CA $242
per adult
Sunday Brunch Sail in Greenport
See all activities in Shelter Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.