Montclair Colony Travel Guide

Shelter Island

Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

฿5,791
per adult
Sunday Brunch Sail in Greenport
Private Luxury Wine Tours of Long Island Pindar Winery

Private Luxury Wine Tours of Long Island Pindar Winery

฿6,552
per adult
Private Luxury Wine Tours of Long Island Pindar Winery
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM

Half Day(PM) North Fork Private Wine & Food Tour by Local Expert

฿14,527
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
See all activities in Shelter Island

Top hotels in Montclair Colony

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ฿8,083 per night from 1 Oct to 2 Oct
฿8,083
฿10,182 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.4/10 Very good! (712 reviews)
"I booked thru Expedia but never checked in because you were SOLD OUzt! Expedia has a problem to fix!"

Reviewed on 2 Sept 2026

Sound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
The price is ฿3,048 per night from 9 Sept to 10 Sept
฿3,048
฿3,506 total
9 Sept - 10 Sept
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very good! (1,000 reviews)
"Reasonable price, nice staff, clean rooms. Fills the need for a short stay!"

Reviewed on 1 Sept 2026

Pier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is ฿3,969 per night from 1 Oct to 2 Oct
฿3,969
฿5,367 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
The Atlantic Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is ฿6,442 per night from 21 Sept to 22 Sept
฿6,442
฿7,980 total
21 Sept - 22 Sept
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,004 reviews)
"Everything was excellent!!!"

Reviewed on 1 Sept 2026

Water's Edge Resort & Spa
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
The price is ฿5,306 per night from 15 Sept to 16 Sept
฿5,306
฿6,891 total
15 Sept - 16 Sept
includes taxes & fees
Stay at this business-friendly hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (573 reviews)
"A well thought out space. Staff is welcoming and helpful. The Room met our expectations. They even offer a beach pass for the Southampton town beach!"

Reviewed on 31 Aug 2026

The Bentley Hotel Southampton
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St Old Saybrook CT
The price is ฿12,237 per night from 3 Sept to 4 Sept
฿12,237
฿15,233 total
3 Sept - 4 Sept
includes taxes & fees
Stay at this spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in their reviews. ...
9.6/10 Exceptional! (1,004 reviews)
"Rooms were newly renovated. Love this place"

Reviewed on 31 Aug 2026

Saybrook Point Resort & Marina
See all 3,993 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.

Where to stay in Montclair Colony

Find the best Montclair Colony areas for the activities you enjoy most.
A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Shelter Island Historical Society and Sunset Beach.

A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

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

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

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Historical Society and Mashomack Preserve are some notable places to visit nearby.

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

Hay Beach

When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.

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 Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Shelter Island Historical Society.

Montclair Colony Travel Guide