Search Hotels in Montclair Colony, Shelter Island

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

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, (441)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is 2.345.914 ₫
3.032.048 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hamlet 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 2.739.348 ₫
3.130.007 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
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, (708)
"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
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, (546)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 3.530.719 ₫
5.322.387 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Harbor Front Inn
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, (394)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is 3.212.138 ₫
3.696.195 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Bentley Hotel Southampton
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
28.6 km from Montclair Colony
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is 2.051.946 ₫
2.359.738 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Clinton Motel
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, (1002)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is 2.660.953 ₫
3.060.096 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Old Saybrook - Westbrook
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, (460)
"🙂"
United States
Jared
The price is 1.763.358 ₫
2.027.862 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
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, (1001)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
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, (1001)
"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 3.054.164 ₫
3.489.382 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Hyatt Place Long Island East End
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, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is 4.453.550 ₫
6.376.722 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Sound View Greenport
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, (228)
"Food!"
United States
Ryan
The price is 4.879.686 ₫
5.575.043 ₫ total
includes taxes & fees
16 Dec - 17 Dec
The Shoals Suites and Slips
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 3.123.956 ₫
3.725.597 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Southampton Long Island Hotel
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
13.8 km from Montclair Colony
8.8 out of 10, Excellent, (212)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is 4.004.641 ₫
5.628.134 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Sagaponack
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 Hampton Maid
Front of property
The Preston House & Hotel

The Preston House & Hotel

The Preston House & Hotel
3.5 star property
29.7 km from Montclair Colony
9.8 out of 10, Exceptional, (372)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is 3.620.106 ₫
4.135.971 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Preston House & Hotel
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, (141)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
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, (974)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Property entrance
The Menhaden

The Menhaden

The Menhaden
3.5 star property
5.9 km from Montclair Colony
9.6 out of 10, Exceptional, (171)
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
United States
Cory
The price is 6.467.719 ₫
8.442.657 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Menhaden
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
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.
View all properties

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 Crescent Beach and Sunset 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 Shelter Island Historical Society and Sunset Beach.

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.

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.

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

Explore a world of travel with Expedia

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.