Montclair Colony Travel Guide
Shelter Island
Visit Montclair Colony
Things to do
Private Luxury Wine Tours of Long Island Pindar Winery
฿6,611
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
฿14,657
per adult
Private Vacation Photoshoot with Photographer The Hamptons
฿9,317
per adult
Top hotels in Montclair Colony
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿6,347 per night from 1 Nov to 2 Nov
฿6,347
฿7,882 total
1 Nov - 2 Nov
includes taxes & fees
Stay at this beach resort in Westbrook. 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! (1,001 reviews)
"Great"
Reviewed on 21 Oct 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,757 per night from 15 Nov to 16 Nov
฿2,757
฿3,171 total
15 Nov - 16 Nov
includes taxes & fees
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. ...
8/10 Very good! (1,002 reviews)
"Staff was friendly. Grounds very well kept. But rooms are very dated."
Reviewed on 22 Oct 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿3,614 per night from 28 Oct to 29 Oct
฿3,614
฿4,973 total
28 Oct - 29 Oct
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
7.2/10 Good! (1,000 reviews)
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Reviewed on 19 Oct 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿5,846 per night from 22 Nov to 23 Nov
฿5,846
฿7,643 total
22 Nov - 23 Nov
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Zey Hotel
439 Main Street Greenport NY
The price is ฿6,124 per night from 25 Oct to 26 Oct
฿6,124
฿6,996 total
25 Oct - 26 Oct
includes taxes & fees
Stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on-site and daily housekeeping. Popular attractions Greenport Harbor Brewing Company ...
9.2/10 Wonderful! (435 reviews)
"The hotel had a good vibe and energy! Lots of artwork and was very charming. It has a bed and breakfast feel to it. The parking is behind the hotel and free and convenient. It’s right on Main Street and walking distance to all restaurants and bars. The staff especially James was warm and friendly ..."
Reviewed on 22 Oct 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is ฿4,839 per night from 31 Oct to 1 Nov
฿4,839
฿5,528 total
31 Oct - 1 Nov
includes taxes & fees
Stay at this business-friendly hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (605 reviews)
"Perfect one day stay. I would stay here again and can recommend it to others."
Reviewed on 22 Oct 2026
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.
Where to stay in Montclair Colony
Find the best Montclair Colony areas for the activities you enjoy most.
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.
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.
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.
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.
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 Shell Beach.
