Find hotels in Montclair Colony, Shelter Island

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Our top choices for Montclair Colony hotels

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, (1002)
"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
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, (445)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ₩125,857
₩162,677 total
includes taxes & fees
Dec 30 - Dec 31
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, (711)
"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 ₩150,120
₩171,529 total
includes taxes & fees
Jan 6 - Jan 7, 2026
House on Chase Creek
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 ₩112,449
₩129,316 total
includes taxes & fees
Dec 30 - Dec 31
Clinton Motel
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 ₩160,024
₩182,828 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hyatt Place Long Island East End
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, (554)
"Room and staff were amazing. "
United States
Manuel
The price is ₩194,840
₩261,803 total
includes taxes & fees
Jan 28 - Jan 29, 2026
The Harbor Front Inn
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, (204)
"Good location. Nice people!! "
United States
Theresa
The price is ₩143,806
₩171,486 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Southampton Long Island Hotel
Indoor pool, open 9:00 AM to 9:00 PM, sun 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 very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is ₩139,697
₩160,652 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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, (463)
"We came in for a family wedding in the area and this hotel was a great location. The mexican restaurant that was down the street is fantastic, great margaritas ! Would definitely use this location again if we were out this way. Thank you for a wonderful stay !"
United States
Robert
The price is ₩96,634
₩111,129 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
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, (412)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is ₩180,388
₩207,536 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Bentley Hotel Southampton
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
6.5 km from Montclair Colony
8.4 out of 10, Very Good, (601)
"Great view but a gas station has a better breakfast. "
United States
Michael
The price is ₩229,512
₩301,437 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Sound View Greenport
Garden Suite King | Premium bedding, down comforters, 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, (232)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is ₩267,413
₩305,518 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Shoals Suites and Slips
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
13.8 km from Montclair Colony
8.8 out of 10, Excellent, (216)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is ₩232,251
₩322,995 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Sagaponack
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
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
18.2 km from Montclair Colony
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
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
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
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
25.9 km from Montclair Colony
9.6 out of 10, Exceptional, (1004)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is ₩445,473
₩548,336 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Saybrook Point Resort & Marina
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
19.2 km from Montclair Colony
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is ₩856,887
₩1,027,936 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Roundtree, Amagansett
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 and neighborhoods for the activities you enjoy most.

Silver Beach

While Silver Beach might 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

When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area.

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Shelter Island Whale's Tail.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

Top Montclair Colony Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"They really take care of us! The location is great! "
Cassiano 4-night trip
Posted 2 days ago
The Bentley Hotel Southampton

Frequently asked questions

What is Montclair Colony like?
You'll be sure to have fun visiting Shelter Island's Montclair Colony neighborhood.
If I need to cancel my hotel reservation in Montclair Colony, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it might still be possible to cancel it and get a refund within a 24-hour period of your booking. Enter dates in and click on "Search", then use the "fully refundable" filter to get the best deals available in Montclair Colony.
Where can I learn more about changing or cancelling my trip to Montclair Colony?
To find more details about changing or cancelling your trip to Montclair Colony, click here.
What is there to do around this Shelter Island neighborhood?
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.