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Oct 2 - Oct 4
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Oct 9 - Oct 11

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Our top choices for Montclair Colony hotels

A waterfront property with a large house, multiple boats docked, and lush greenery.

1. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
6.7 km from Montclair Colony
9.4 out of 10, Exceptional, (670 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
The price is ₩438,719
₩501,236 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

2. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
5.9 km from Montclair Colony
9.0 out of 10, Wonderful, (661 reviews)
"Great location"
United States
Jordan
The price is ₩303,447
₩385,358 total
includes taxes & fees
Oct 25 - Oct 26
The Harbor Front Inn
Front of property - evening/night

3. Shelter Island House

Shelter Island House
3.5 star property
2.7 km from Montclair Colony
8.4 out of 10, Very good, (66 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is ₩272,507
₩311,328 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

4. 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, (1,006 reviews)
"Great location, rooms were big and clean."
United States
Renee
The price is ₩145,021
₩166,774 total
includes taxes & fees
Oct 4 - Oct 5
Quality Inn Old Saybrook - Westbrook
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

5. 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, (342 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is ₩273,285
₩346,081 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips
A spacious room with wicker furniture, large windows, and a view of the sea.

6. Sound View Greenport

Sound View Greenport
4.0 star property
6.5 km from Montclair Colony
8.4 out of 10, Very good, (739 reviews)
"Great one night stay."
United States
Irene
The price is ₩338,857
₩425,817 total
includes taxes & fees
Oct 25 - Oct 26
Sound View Greenport
A two-story house with a balcony, outdoor seating area, and a variety of plants.

7. Zey Hotel

Zey Hotel
3.5 star property
6.1 km from Montclair Colony
9.2 out of 10, Wonderful, (411 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is ₩228,499
₩261,058 total
includes taxes & fees
Sep 29 - Sep 30
Zey Hotel
A serene landscape with a calm body of water reflecting trees with autumn foliage.

8. House on Chase Creek

House on Chase Creek
2.5 star property
3.5 km from Montclair Colony
9.4 out of 10, Exceptional, (86 reviews)
"Nice owner.. convenient location"
United States
Calvin
The price is ₩291,504
₩333,047 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek
A parking lot with a building in the background.

9. Clinton Motel

Clinton Motel
2.5 star property
28.6 km from Montclair Colony
8.6 out of 10, Excellent, (337 reviews)
"Hotel was clean and the staff was pleasant. The pool was wonderful! I would stay there again."
United States
Selena
The price is ₩105,617
₩121,460 total
includes taxes & fees
Sep 29 - Sep 30
Clinton Motel
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

10. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
5.5 km from Montclair Colony
10.0 out of 10, Exceptional, (171 reviews)
"Excellent stay. The room was clean and stylish. Can’t wait to come back"
United States
Sarah
The price is ₩440,073
₩502,794 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows
A sign for Pier Blue Guesthouse with a logo and name.

11. 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, (1,014 reviews)
"It was a decent stay, we came in for a family reunion and originally planning to camp but weren’t able to due to the storm so we found this last min at a decent price point. Staff was very friendly when we came in, seems to be family operated which I like. Room was clean could use some updates but I liked the almost beachy vibe they have."
United States
virginia
The price is ₩105,888
₩121,771 total
includes taxes & fees
Sep 29 - Sep 30
Pier Blue Inn Old Saybrook - Essex
A bedroom with a bed, bedside tables, a lamp, a window, and a door.

12. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
2.8 km from Montclair Colony
8.2 out of 10, Very good, (46 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
The price is ₩424,501
₩485,001 total
includes taxes & fees
Oct 1 - Oct 2
West Neck Guesthouse
Terrace/patio

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
6.6 km from Montclair Colony
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is ₩319,439
₩515,183 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

14. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
19.9 km from Montclair Colony
9.6 out of 10, Exceptional, (591 reviews)
"nice room for the price in season"
United States
Frank
The price is ₩169,275
₩232,082 total
includes taxes & fees
Oct 4 - Oct 5
The Bentley Hotel Southampton
A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.

15. 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, (1,002 reviews)
"Staff was beyond amazing and the hotel was perfect! Rooms comfy and bathroom a great size!"
United States
Veronica
The price is ₩211,235
₩241,337 total
includes taxes & fees
Oct 21 - Oct 22
Hyatt Place Long Island East End
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

16. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
26.8 km from Montclair Colony
8.8 out of 10, Excellent, (1,011 reviews)
"Wonderful"
United States
Bill
The price is ₩242,717
₩302,486 total
includes taxes & fees
Oct 7 - Oct 8
Water's Edge Resort & Spa
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

17. The Menhaden

The Menhaden
3.5 star property
5.9 km from Montclair Colony
9.6 out of 10, Exceptional, (191 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is ₩451,609
₩570,117 total
includes taxes & fees
Sep 29 - Sep 30
The Menhaden
An outdoor patio area with string lights, tables, chairs, and a fire pit.

18. The Chequit

The Chequit
3.0 star property
3.8 km from Montclair Colony
9.2 out of 10, Wonderful, (64 reviews)
"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"
United States
Kristin
The price is ₩280,293
₩320,234 total
includes taxes & fees
Oct 4 - Oct 5
The Chequit
A living room with a stone fireplace, grey sofas, and a coffee table.

19. The Captain Stannard

The Captain Stannard
3.0 star property
27.4 km from Montclair Colony
9.8 out of 10, Exceptional, (284 reviews)
"Had a great stay. Everything was fantastic."
United States
Deborah
The price is ₩316,742
₩351,584 total
includes taxes & fees
Sep 29 - Sep 30
The Captain Stannard
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

20. Shorewood Inn

Shorewood Inn
2.5 star property
23.2 km from Montclair Colony
8.4 out of 10, Very good, (821 reviews)
"Close to all , great for a night or 2- priced right"
United States
KAREN
The price is ₩115,773
₩132,266 total
includes taxes & fees
Sep 29 - Sep 30
Shorewood Inn
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.
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

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.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

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

A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

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

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

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.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Wades Beach and Mashomack Preserve.

Top Montclair Colony Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"The hotel was just what we expected, cozy and comfortable and nestled right into central Greenport. Close to everything, dinner spots just steps away. Will definitely return."
Arnold 2-night trip
Posted less than an hour ago
The Harbor Front Inn

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.