Montclair Colony

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

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

Shelter Island Historical Society

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

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

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

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

CA $218
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

CA $187
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

Montclair Colony Hotel Deals

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is CA $152 per night from Aug 3 to Aug 4
CA $152
CA $174 total
Aug 3 - Aug 4
includes taxes & 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 ...
7.6/10 Good! (1,008 reviews)
Excellent Place to Stay!!!...5 Stars & More!!
"We stayed 5 days! Customer service was great ;) Housekeeping was great, the cafe in the morning was excellent! Lounge area if you wanted to go out in the evening they had Pool, Darts, & Karaoke If you didn't want to go to the Beach, they had a Pool/Gym Right near the Highway & Route 1 We had a wonderful ..."

Reviewed on Jul. 10, 2025

Quality Inn Old Saybrook - Westbrook
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 CA $110 per night from Jul 20 to Jul 21
CA $110
CA $126 total
Jul 20 - Jul 21
includes taxes & 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. ...
7.6/10 Good! (992 reviews)
"The roadside in exceeded my expectations in all areas"

Reviewed on Jul. 9, 2025

Pier Blue Inn Old Saybrook - Essex
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is CA $487 per night from Jul 17 to Jul 18
CA $487
CA $588 total
Jul 17 - Jul 18
includes taxes & 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 ...
9.4/10 Exceptional! (1,010 reviews)
"Really special place"

Reviewed on Jul. 15, 2025

Saybrook Point Resort & Marina
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is CA $344 per night from Jul 20 to Jul 21
CA $344
CA $428 total
Jul 20 - Jul 21
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (875 reviews)
"The staff was very welcoming. The room was clean and very spacious. The location is great. Would highly recommend."

Reviewed on Jul. 14, 2025

The Atlantic Hotel
Baron's Cove

Baron's Cove

4 out of 5
31 West Water Street, Sag Harbor, NY
The price is CA $767 per night from Aug 12 to Aug 13
CA $767
CA $964 total
Aug 12 - Aug 13
includes taxes & fees
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (265 reviews)
"Really beautiful and clean property that is very convenient and great amenities."

Reviewed on Jun. 27, 2025

Baron's Cove
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is CA $567 per night from Jul 22 to Jul 23
CA $567
CA $718 total
Jul 22 - Jul 23
includes taxes & 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! (536 reviews)
Excellent views
"Nice quiet place with excellent views to spend the night"

Reviewed on Jul. 13, 2025

Sound View Greenport
See all 4,076 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

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.

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 Shell Beach and Mashomack Preserve.

Shorewood
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Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, 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

Montclair Colony

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