A lighthouse on a grassy dune with a beach and water in the background.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Middle Island cottages

Terrace/patio

1. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic experience. Cabin was clean and quiet. Beautiful mornings on the water."
United States
Leah O.
$920 nightly
The price is $936
Aug 20 - Aug 21
Total with taxes and fees
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Exterior

2. 4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.8 out of 10, Exceptional, (19 reviews)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
United States
Richard C.
$920 nightly
The price is $936
Aug 23 - Aug 24
Total with taxes and fees
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Exterior

3. 6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Riverhead
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay. Very quiet and relaxing. Excellent location to many wineries. Would definitely stay again."
United States
Donna M.
$726 nightly
The price is $739
Sep 14 - Sep 15
Total with taxes and fees
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
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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Top Middle Island Hotel Reviews

Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

8/10 Good
"The room was very clean. The staff was woundful. The only problem i had was the hole place smelled like marijuana. Dont get me wrong i dont mind it a little BUT it was so strong!"
Theresa 3-night trip
Posted 2 hours ago
Jake's 58 Casino Hotel - Adult Only

Find out more about Middle Island

Middle Island Cottages information

Number of reviews
34
Accommodation
59 Cottages
Lowest Price
$739
Highest Price
$936

Frequently asked questions

Why book your cottage in Middle Island with Expedia?
Expedia has some wonderful cottages in Middle Island, so start packing for a memorable vacation on nature's doorstep. If you have a budget, click on how much you want to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the perfect place whatever your plans or style of travel.
How can I find cheap cottages in Middle Island?
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