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

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

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

P8,435
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

P7,922
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

Top hotels in Montclair Colony

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 P4,658 per night from Sep 30 to Oct 1
P4,658
P5,357 total
Sep 30 - Oct 1
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. ...
7.8/10 Good! (1,004 reviews)
"Property was a little dated, but very comfortable. The staff was terrific."

Reviewed on Sep 27, 2025

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is P5,684 per night from Oct 13 to Oct 14
P5,684
P6,537 total
Oct 13 - Oct 14
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! (1,011 reviews)
"Liked having and using pool. didn't realize there would be a swimming lesson going on at same time. As this was a quick stop over on our way to Bar Harbor, it fit our needs. Since the room was on the street side it was a bit noisy even with fan running all the time. The room was clean and comfortable ..."

Reviewed on Sep 28, 2025

Quality Inn Old Saybrook - Westbrook
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is P14,431 per night from Oct 27 to Oct 28
P14,431
P19,333 total
Oct 27 - Oct 28
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! (574 reviews)
"Clean and beautiful view"

Reviewed on Sep 16, 2025

Sound View Greenport
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is P8,844 per night from Oct 5 to Oct 6
P8,844
P11,558 total
Oct 5 - Oct 6
includes taxes & 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. ...
7/10 Good! (942 reviews)
"Clean"

Reviewed on Sep 23, 2025

The Atlantic Hotel
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is P20,403 per night from Oct 14 to Oct 15
P20,403
P24,918 total
Oct 14 - Oct 15
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! (1,013 reviews)
"My husband used the spa and said it was excellent. The housekeeping staff was generally good - -forgot some tasks a couple of times. Front of the house staff excellent. Special shoutout to Jack!! Very surprised that there was no inroom safe. Bathroom needs a remodel -needs taller counters…as well ..."

Reviewed on Sep 26, 2025

Saybrook Point Resort & Marina
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd, Southampton, NY
The price is P10,330 per night from Oct 1 to Oct 2
P10,330
P11,802 total
Oct 1 - Oct 2
includes taxes & fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (342 reviews)
"Staff and management were very helpful with the room change request. Property was ideal with large rooms and comfort for a quick stay in the hamptons. Great value!"

Reviewed on Sep 26, 2025

The Bentley Hotel Southampton
See all 3,989 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 Sunset Beach and Crescent 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 Mashomack Preserve 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 Mashomack Preserve, 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