Montclair Colony, NY

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 carefree 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 carefree 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

4/5(1 review)

You can spend time studying 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

$148
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

$139
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

Montclair Colony Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
$85 nightly
The price is $98 total per night from Sep 8 to Sep 9
$98 total
Sep 8 - Sep 9
Total with taxes and fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Pier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
$174 nightly
The price is $199 total per night from Oct 5 to Oct 6
$199 total
Oct 5 - Oct 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Atlantic Hotel
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
$98 nightly
The price is $112 total per night from Sep 14 to Sep 15
$112 total
Sep 14 - Sep 15
Total with taxes and fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn Old Saybrook - Westbrook
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
$431 nightly
The price is $495 total per night from Sep 7 to Sep 8
$495 total
Sep 7 - Sep 8
Total with taxes and fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
Saybrook Point Resort & Marina
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
$306 nightly
The price is $350 total per night from Sep 22 to Sep 23
$350 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (554 reviews)
"Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound"

Reviewed on Aug 18, 2025

Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
$230 nightly
The price is $262 total per night from Oct 5 to Oct 6
$262 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (500 reviews)
"Great location ,beautiful hotel,nice staff"

Reviewed on Aug 25, 2025

The Harbor Front Inn
See all 3,973 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 neighborhoods around Montclair Colony

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Menantic Creek

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

Menantic Creek
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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 Crescent Beach and Sunset Beach.

Silver Beach
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Shorewood

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

Shorewood
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Coecles Harbor

When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Sunset Beach, some noteworthy sights in the nearby area.

Coecles Harbor
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Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Hay Beach
See our Where To Stay guide

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Montclair Colony, NY

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