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

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

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

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

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

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

S$204
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

S$175
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

Top hotels in Montclair Colony

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is S$162 per night from 5 Aug to 6 Aug
S$162
5 Aug - 6 Aug
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! (1,005 reviews)
"Just a little tired looking, but very nice staff. Everything went well. Thank you. Good value for everything."

Reviewed on 21 Jul, 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 S$118 per night from 30 Jul to 31 Jul
S$118
30 Jul - 31 Jul
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! (1,001 reviews)
"Very convenient to the beaches and very clean room. I had some trouble with the door lock but nothing major. I'm a doofus. Will definitely return."

Reviewed on 16 Jul, 2025

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is S$741 per night from 21 Aug to 22 Aug
S$741
21 Aug - 22 Aug
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! (541 reviews)
"Every room comes with an ocean view, steps down to the beach. Activities at night. Band at the ocean on certain nights. Will be back every year! Help with bags and getting to room by golf cart."

Reviewed on 22 Jul, 2025

Sound View Greenport
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is S$542 per night from 12 Aug to 13 Aug
S$542
12 Aug - 13 Aug
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! (1,007 reviews)
"Rooms were large and spacious but quite dark. The Choo Choo lounge and the outside bar were very pleasant. The onsite dining restaurant was disappointing, food was below expectations and did not live up to their rating. Staff were all very pleasant. Parking was a difficult but it is high season."

Reviewed on 21 Jul, 2025

Saybrook Point Resort & Marina
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
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! (883 reviews)
Yes
"Great"

Reviewed on 23 Jul, 2025

Get rates
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd, Southampton, NY
The price is S$456 per night from 19 Aug to 20 Aug
S$456
19 Aug - 20 Aug
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.4/10 Exceptional! (288 reviews)
"We could not recommend this property more! The rooms are fabulous and the grounds are beautiful. We had a room on the ground and our dog loved the easy access outside. The rooms are decorated beautifully as well - very chic and spacious! Cant wait to come back here in the Fall."

Reviewed on 19 Jul, 2025

The Bentley Hotel Southampton
See all 4,023 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

Default Image

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Wades Beach and Shelter Island Historical Society.

Menantic Creek
Default Image

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
Default Image

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 Wades Beach and Mashomack Preserve.

Shorewood
Default Image

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
Default Image

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