Montclair Colony Travel Guide

Shelter Island

Popular places to visit

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Gardiner's Bay Country Club

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

Shelter Island Whale's Tail

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Mashomack Preserve

Wades Beach

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Wades Beach

Shell Beach

Why not spend a care-free afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Shell Beach

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

Things to do

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

฿4,848
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

฿4,553
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

฿11,104
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM
See all activities in Shelter Island

Top hotels in Montclair Colony

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
Stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
7/10 Good! (913 reviews)
"Nice place. Recommend."

Reviewed on 18 Aug 2025

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The Atlantic Hotel
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is ฿11,579 per night from 26 Aug to 27 Aug
฿11,579
฿13,967 total
26 Aug - 27 Aug
includes taxes & fees
Stay at this 3.5-star 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 ...
9.4/10 Exceptional! (1,004 reviews)
"The bed and pillows are the best I’ve ever slept on!! Very clean! Had a wonderful dinner at Fresh Salt. Spa was very nice and had great services."

Reviewed on 18 Aug 2025

Saybrook Point Resort & Marina
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is ฿9,435 per night from 9 Sept to 10 Sept
฿9,435
฿12,374 total
9 Sept - 10 Sept
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (560 reviews)
"Feels like a remote vacation destination just a couple of hours from home. Self-contained property with private beach and pool away from crowds and tourists, but close to town."

Reviewed on 13 Aug 2025

Sound View Greenport
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ฿3,324 per night from 15 Sept to 16 Sept
฿3,324
฿3,822 total
15 Sept - 16 Sept
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,011 reviews)
"Perfect spot for my visit"

Reviewed on 17 Aug 2025

Quality Inn Old Saybrook - Westbrook
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd, Southampton, NY
The price is ฿7,137 per night from 9 Sept to 10 Sept
฿7,137
฿9,083 total
9 Sept - 10 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 ...
9.4/10 Exceptional! (315 reviews)
Such a gem!
"Pleasantly surprised at just how adorable this place was. Also, the room was very large!"

Reviewed on 15 Aug 2025

The Bentley Hotel Southampton
Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
Stay at this hotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.2/10 Wonderful! (176 reviews)
"Great place!"

Reviewed on 17 Aug 2025

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Greenporter Hotel
See all 3,972 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.

Other neighbourhoods around Montclair Colony

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Menantic Creek

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

Menantic Creek
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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.

Silver Beach
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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 Sunset Beach and Crescent Beach.

Shorewood
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Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Coecles Harbor
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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.

Hay Beach

Montclair Colony Travel Guide