Montclair Colony Travel Guide

Shelter Island

Things to do

Private Luxury Wine Tours of Long Island Pindar Winery

Private Luxury Wine Tours of Long Island Pindar Winery

฿6,611
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

฿14,657
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
Private Vacation Photoshoot with Photographer The Hamptons

Private Vacation Photoshoot with Photographer The Hamptons

฿9,317
per adult
Private Vacation Photoshoot with Photographer The Hamptons
See all activities in Shelter Island

Top hotels in Montclair Colony

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is ฿6,320 per night from 1 Nov to 2 Nov
฿6,320
฿7,848 total
1 Nov - 2 Nov
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! (1,001 reviews)
"Great"

Reviewed on 21 Oct 2026

Water's Edge Resort & Spa
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 ฿2,746 per night from 15 Nov to 16 Nov
฿2,746
฿3,157 total
15 Nov - 16 Nov
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! (1,001 reviews)
"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"

Reviewed on 21 Oct 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 ฿3,599 per night from 28 Oct to 29 Oct
฿3,599
฿4,952 total
28 Oct - 29 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 ...
7.2/10 Good! (1,005 reviews)
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"

Reviewed on 19 Oct 2026

The Atlantic Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ฿5,821 per night from 22 Nov to 23 Nov
฿5,821
฿7,611 total
22 Nov - 23 Nov
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 ...
Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is ฿6,124 per night from 26 Oct to 27 Oct
฿6,124
฿6,996 total
26 Oct - 27 Oct
includes taxes & fees
Stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on-site and daily housekeeping. Popular attractions Greenport Harbor Brewing Company ...
Zey Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
The price is ฿4,704 per night from 10 Nov to 11 Nov
฿4,704
฿5,374 total
10 Nov - 11 Nov
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! (604 reviews)
"Gorgeous room! Felt like we were home"

Reviewed on 20 Oct 2026

The Bentley Hotel Southampton
See all 3,938 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 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 Sunset Beach and Shell Beach.

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 Wades Beach and Shelter Island Historical Society.

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, Gardiner's Bay Country Club 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 Gardiner's Bay Country Club and Greenport Carousel, 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 Wades Beach and Shell Beach.

Montclair Colony Travel Guide