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Find hotels in Montclair Colony, Shelter Island

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Sep 25 - Sep 27
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Oct 2 - Oct 4

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Our top choices for Montclair Colony hotels

Outdoor dining

1. The Chequit

The Chequit
3.0 star property
2.4 mi from Montclair Colony
9.0 out of 10, Wonderful, (60 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
$178 nightly
The price is $203
Oct 8 - Oct 9
Total with taxes and fees
The Chequit
Exterior

2. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
3.4 mi from Montclair Colony
9.4 out of 10, Exceptional, (341 reviews)
"Loved everything about our stay!"
United States
Melissa
$254 nightly
The price is $286
Oct 1 - Oct 2
Total with taxes and fees
The Shoals Suites and Slips
Front of property - evening/night

3. Shelter Island House

Shelter Island House
3.5 star property
1.7 mi 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
$201 nightly
The price is $230
Oct 4 - Oct 5
Total with taxes and fees
Shelter Island House
Exterior

4. Zey Hotel

Zey Hotel
3.5 star property
3.8 mi from Montclair Colony
9.2 out of 10, Wonderful, (406 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
$169 nightly
The price is $193
Oct 5 - Oct 6
Total with taxes and fees
Zey Hotel
View from property

5. House on Chase Creek

House on Chase Creek
2.5 star property
2.2 mi from Montclair Colony
9.4 out of 10, Exceptional, (86 reviews)
"Nice owner.. convenient location"
United States
Calvin
$215 nightly
The price is $246
Oct 5 - Oct 6
Total with taxes and fees
House on Chase Creek
Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
3.6 mi from Montclair Colony
9.0 out of 10, Wonderful, (659 reviews)
"Great location"
United States
Jordan
$246 nightly
The price is $281
Oct 19 - Oct 20
Total with taxes and fees
The Harbor Front Inn
Beach bar

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
3.4 mi from Montclair Colony
10.0 out of 10, Exceptional, (169 reviews)
"I love this place"
United States
Sirikhwan
$267 nightly
The price is $304
Oct 21 - Oct 22
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
Resort view

8. Sound View Greenport

Sound View Greenport
4.0 star property
4.1 mi from Montclair Colony
8.4 out of 10, Very good, (732 reviews)
"Great one night stay."
United States
Irene
$267 nightly
The price is $305
Oct 5 - Oct 6
Total with taxes and fees
Sound View Greenport
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, WiFi (free), bed sheets

9. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
1.8 mi 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
$314 nightly
The price is $358
Oct 1 - Oct 2
Total with taxes and fees
West Neck Guesthouse
Terrace/patio

10. American Beech Hotel

American Beech Hotel
3.5 star property
3.8 mi from Montclair Colony
9.0 out of 10, Wonderful, (207 reviews)
"Great location, very friendly and helpful "
United States
Mary
$274 nightly
The price is $313
Sep 22 - Sep 23
Total with taxes and fees
American Beech Hotel
Flat-screen TV

11. North Fork Resort

North Fork Resort
3.0 star property
4.1 mi from Montclair Colony
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$270 nightly
The price is $308
Oct 19 - Oct 20
Total with taxes and fees
North Fork Resort
Seasonal outdoor pool, open 9:00 AM to 8:30 PM, pool umbrellas

12. Oyster Estate

Oyster Estate
4.0 star property
3.7 mi from Montclair Colony
9.2 out of 10, Wonderful, (291 reviews)
"Clean, great amenities, and friendly staff!"
United States
Elizabeth
$296 nightly
The price is $338
Oct 8 - Oct 9
Total with taxes and fees
Oyster Estate
Condo | Terrace/patio

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
4.1 mi from Montclair Colony
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
$372 nightly
The price is $426
Oct 5 - Oct 6
Total with taxes and fees
Cliffside Resort Condominiums
Building design

14. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
4.2 mi from Montclair Colony
9.4 out of 10, Exceptional, (666 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
$324 nightly
The price is $370
Oct 4 - Oct 5
Total with taxes and fees
Sag Harbor Inn
Property entrance

15. The Menhaden

The Menhaden
3.5 star property
3.6 mi from Montclair Colony
9.6 out of 10, Exceptional, (191 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
$409 nightly
The price is $461
Oct 7 - Oct 8
Total with taxes and fees
The Menhaden
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

16. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
4.3 mi from Montclair Colony
9.0 out of 10, Wonderful, (308 reviews)
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
United States
Miguel
$490 nightly
The price is $560
Oct 5 - Oct 6
Total with taxes and fees
Faraway Sag Harbor
Restaurant

17. Hamlet Inn

Hamlet Inn
2.0 star property
12.5 mi from Montclair Colony
8.6 out of 10, Excellent, (504 reviews)
"I loved staying here! Great location, great rooms, and the woman who runs it (Denise?) is so incredibly helpful in directing guests to the best beaches, restaurants, least traffic routes, activities. Will stay here many times in the future!"
United States
Thomas
$165 nightly
The price is $186
Sep 22 - Sep 23
Total with taxes and fees
Hamlet Inn
Reception

18. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
12.4 mi from Montclair Colony
9.6 out of 10, Exceptional, (589 reviews)
"nice room for the price in season"
United States
Frank
$147 nightly
The price is $168
Oct 5 - Oct 6
Total with taxes and fees
The Bentley Hotel Southampton
Exterior

19. Shorewood Inn

Shorewood Inn
2.5 star property
14.4 mi from Montclair Colony
8.4 out of 10, Very good, (819 reviews)
"Close to all , great for a night or 2- priced right"
United States
KAREN
$86 nightly
The price is $98
Oct 5 - Oct 6
Total with taxes and fees
Shorewood Inn
Property grounds

20. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
16.6 mi from Montclair Colony
8.0 out of 10, Very good, (1,006 reviews)
"Pleasant one night stay in our trek"
United States
Carolyn
$80 nightly
The price is $93
Oct 8 - Oct 9
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
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. Learn more about Montclair Colony
Learn more about Montclair Colony
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 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 pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Historical Society and Mashomack Preserve, some noteworthy sights in the nearby area.

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 Greenport Carousel and Greenport Harbor Brewing Company 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 Mashomack Preserve and Shelter Island Historical Society.

Top Montclair Colony Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The grounds and the interior of the property were beautifully maintained and tastefully appointed. The staff is exceptionally friendly. The bathroom in my room was dated and needed remodeling. Wall dispensers of shampoo, conditioner and body wash were not installed in shower as is generally offered in most 4 star hotels. While there is a coffee machine in guest rooms, there is no complimentary coffee offered in the lobby."
Russell 1-night trip
Posted 3 hours ago
Water's Edge Resort & Spa

Frequently asked questions

When is the best time to go to Montclair Colony?
The best time to visit Montclair Colony is during the spring (late April to early June) and fall (September to October) for pleasant weather and fewer crowds.

Spring brings blooming flowers and comfortable temperatures, ideal for exploring the outdoor attractions and enjoying the scenic beauty without the summer heat. Many local shops and cafes are open, offering a relaxed experience before the peak tourist season. This period is particularly good for couples looking for a quiet getaway.

Fall offers crisp air, stunning foliage, and a variety of seasonal events like harvest festivals. The weather is still mild enough for outdoor activities, and the vibrant colors of the trees make for beautiful drives and walks.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Montclair Colony.
How much is the nightly rate at a Montclair Colony hotel?
Prices for hotels in Montclair Colony often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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