Montclair Colony Travel Guide

Shelter Island

Popular places to visit

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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
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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
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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
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Shelter Island Historical Society

You can enjoy some culture when you stop by Shelter Island Historical Society in Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society
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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
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Menhadden Lane Beach

Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?

Menhadden Lane Beach

Things to do

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

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

฿4,957
Per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Image for Private Guided Wine Country Bike Tour in Mattituck

Private Guided Wine Country Bike Tour in Mattituck

฿6,763
Per adult
Private Guided Wine Country Bike Tour in Mattituck
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Private Guided Wine Country Bike Tour For Two (Mattituck)

฿27,527
Per adult
Private Guided Wine Country Bike Tour For Two (Mattituck)
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 ฿2,559 per night from 29 Sep to 30 Sep
฿2,559
per night
29 Sep - 30 Sep
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. ...
7.6/10 Good! (858 reviews)
"It is in a nice a part of Old Saybrook."

Reviewed on 27 Sep 2024

Pier Blue Inn Old Saybrook - Essex
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
The price is ฿8,507 per night from 30 Sep to 1 Oct
฿8,507
per night
30 Sep - 1 Oct
Stay at this 4-star hotel in Sag Harbor. 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! (173 reviews)
"Bar fireplace, live music, cozy, charming…"

Reviewed on 25 Sep 2024

Baron's Cove
The Harbor Front Inn
The Harbor Front Inn
3.5 out of 5
209 Front St, Greenport, NY
The price is ฿6,305 per night from 29 Sep to 30 Sep
฿6,305
per night
29 Sep - 30 Sep
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (402 reviews)
"Beautiful location right by the water. Easy walkable access to to boardwalk, shops and dining."

Reviewed on 23 Sep 2024

The Harbor Front Inn
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 ฿2,824 per night from 14 Oct to 15 Oct
฿2,824
per night
14 Oct - 15 Oct
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 ...
7.4/10 Good! (1,001 reviews)
"I stayed a Friday night. The property looks rundown from the outside but is better inside. Rooms have good ventilation and air control, and they are very clean. Breakfast is included and is excellent. Nearby dining options are outstanding"

Reviewed on 14 Sep 2024

Quality Inn Old Saybrook - Westbrook
The Sagaponack
The Sagaponack
3 out of 5
3720 Montauk Hwy, Wainscott, NY
The price is ฿5,636 per night from 29 Sep to 30 Sep
฿5,636
per night
29 Sep - 30 Sep
Stay at this 3-star B&B in Wainscott. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.6/10 Excellent! (105 reviews)
"Nicely renovated property inbetween Bridgehampton and Southampton. Nice well equipped room. Free snacks, beach access and beach parking pass."

Reviewed on 23 Sep 2024

The Sagaponack
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is ฿11,627 per night from 29 Oct to 30 Oct
฿11,627
per night
29 Oct - 30 Oct
Stay at this 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 their reviews. ...
9.4/10 Exceptional! (1,001 reviews)
"We liked your hotel but it seems like it might be in need of a makeover. Our room had lots of bulky traditional furniture which seemed a little worn Living room tv did not have streaming services."

Reviewed on 19 Sep 2024

Saybrook Point Resort & Marina
See all 3,974 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 Mashomack Preserve.

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 Sunset Beach and Shell 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 Mashomack Preserve and Sunset Beach.

Shorewood
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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.

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