Search Hotels in Montclair Colony, Shelter Island

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21 Dec - 22 Dec
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22 Dec - 23 Dec
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Our top choices for Montclair Colony hotels

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
20.2 km from Montclair Colony
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is 2.605.185 ₫
3.367.267 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hamlet Inn
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
23.2 km from Montclair Colony
8.4 out of 10, Very good, (710)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
3.5 km from Montclair Colony
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is 2.740.181 ₫
3.130.959 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
26.7 km from Montclair Colony
8.0 out of 10, Very good, (1005)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
Pier Blue Inn Old Saybrook - Essex
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
28.6 km from Montclair Colony
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is 2.052.570 ₫
2.360.456 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Clinton Motel
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
5.9 km from Montclair Colony
8.8 out of 10, Excellent, (548)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 3.528.841 ₫
5.319.557 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Harbor Front Inn
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
6.5 km from Montclair Colony
8.6 out of 10, Excellent, (599)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is 4.100.140 ₫
5.972.189 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Sound View Greenport
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
29.7 km from Montclair Colony
9.2 out of 10, Wonderful, (1002)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
The price is 2.974.911 ₫
3.398.835 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Hyatt Place Long Island East End
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
26.8 km from Montclair Colony
7.2 out of 10, Good, (461)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveller
The price is 1.763.894 ₫
2.028.478 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Garden Suite King | Premium bedding, down duvets, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
5.5 km from Montclair Colony
9.4 out of 10, Exceptional, (230)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is 4.881.170 ₫
5.576.737 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Shoals Suites and Slips
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
19.9 km from Montclair Colony
9.6 out of 10, Exceptional, (401)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is 3.292.679 ₫
3.788.202 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
29.9 km from Montclair Colony
7.8 out of 10, Good, (1001)
"The staff was friendly. The room was good. "
United States
Narida
The price is 2.661.762 ₫
3.061.026 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Old Saybrook - Westbrook
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
19.3 km from Montclair Colony
7.2 out of 10, Good, (975)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Exterior
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
6.1 km from Montclair Colony
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is 4.710.385 ₫
6.434.281 ₫ total
includes taxes & fees
22 Dec - 23 Dec
American Beech Hotel
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
17.9 km from Montclair Colony
8.6 out of 10, Excellent, (203)
"Good location. Nice people!! "
United States
Theresa
The price is 3.124.906 ₫
3.726.730 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Southampton Long Island Hotel
Property grounds
The Hampton Maid

The Hampton Maid

The Hampton Maid
2.5 star property
22.2 km from Montclair Colony
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The price is 7.460.302 ₫
8.523.395 ₫ total
includes taxes & fees
26 Dec - 27 Dec
The Hampton Maid
Front of property – evening/night
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
16.7 km from Montclair Colony
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is 7.894.500 ₫
9.921.544 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Mill House Inn
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
5.5 km from Montclair Colony
9.8 out of 10, Exceptional, (142)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Exterior
Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only
2.5 star property
24.7 km from Montclair Colony
9.4 out of 10, Exceptional, (312)
"Relaxing stay"
United States
Kristin
Aqua by American Beech - Adults Only
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
13.8 km from Montclair Colony
8.8 out of 10, Excellent, (215)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is 4.002.512 ₫
5.625.142 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Sagaponack
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.
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Where to stay in Montclair Colony

Find the best Montclair Colony areas for the activities you enjoy most.

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 Crescent Beach.

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.

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 Crescent Beach.

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 Mashomack Preserve and Shelter Island Historical Society.

Top Montclair Colony Hotel Reviews

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

10/10 Excellent
"Loved the 2 bar options on the property."
Jennifer 1-night trip
Posted 2 months ago
Hampton Bays Hotel on Main

Frequently asked questions

What is Montclair Colony like?
You'll be sure to have fun exploring Shelter Island's Montclair Colony neighbourhood.
If I need to cancel my hotel reservation in Montclair Colony, will I receive a refund?
Yes, the majority of hotel reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within a 24-hour period of your booking. Enter dates in and click on "Search", then you can filter by "fully refundable" to get the best deals available in Montclair Colony.
What is there to do around this Shelter Island neighbourhood?
A few places to visit in the area around Montclair Colony include Shell Beach, Wades Beach and Shelter Island Historical Society. When you're sightseeing in Shelter Island, Havens House and Sylvester Manor are also worth a stop.