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Compare 56 Cottages in Middle Island with updated reviews, rates, and availability.

Gorgeous NEW East End cottage along water! Minutes from Hamptons and wineries!
Smart TV, fireplace, video games, stereo
Gorgeous NEW East End cottage along water! Minutes from Hamptons and wineries!
10.0 out of 10, Exceptional, (73)
"We were there just for one night and didn't get to spend enough time at the house. Wish it could have been longer! This was a beautiful property. The house is amazing. Will come back again."
The price is $372
includes taxes & fees
$372 per night
Oct 2 - Oct 3
Gorgeous NEW East End cottage along water! Minutes from Hamptons and wineries!
Cozy Riverside Cottage
Property grounds
Cozy Riverside Cottage
10.0 out of 10, Exceptional, (1)
"Cottage is very comfortable and clean. Neighborhood is quiet and in natural surroundings. Be prepared for spotty reception (screenshot access code) but WiFi is excellent in home, so is the TV/music system. Over all, excellent value and great accommodations in a beautiful spot. Only needed it for the weekend, but would book as a destination for some peace and quiet."
Cozy Riverside Cottage
Wine Country Cozy Home Away in the Woods
Exterior
Wine Country Cozy Home Away in the Woods
10.0 out of 10, Exceptional, (24)
"Nadia and Alan are gracious hosts who have thought of every detail. The cottage was a perfect home for me as I worked on many Zoom calls with no difficulty. The location was great as I was able to walk to the town for small meals and also to a local restaurant that was delightful. Highly recommend and have fun in NoFo!"
Wine Country Cozy Home Away in the Woods
Charming Patchogue Cottage!!!
Fridge, oven, stovetop, coffee/tea maker
Charming Patchogue Cottage!!!
10.0 out of 10, Exceptional, (5)
"Loved it. Had everything we needed for a short stay to visit family. Perfect location, beautiful decor and all the necessities plus more! Thank you Brianna and Stephen for a wonderful stay…"
Charming Patchogue Cottage!!!
Cozy Country Cottage #2
Fridge, microwave, oven, stovetop
Cozy Country Cottage #2
6.0 out of 10, (4)
"Great little cottage. Slept 4 comfortably. Was clean and had a washer and dryer. Would rent again. "
The price is $296
includes taxes & fees
$296 per night
Sep 30 - Oct 1
Cozy Country Cottage #2
Charming and Bright Cottage with Salt Water Pool
Interior
Charming and Bright Cottage with Salt Water Pool
10.0 out of 10, Exceptional, (5)
"My husband and I stayed here for a weekend in September and loved every minute. Cottage was well decorated, very clean and had everything you would need. We loved the outdoor shower and the host was so accommodating and thoughtful. Highly recommend and hope to return soon. "
Charming and Bright Cottage with Salt Water Pool
A Hidden Gem! Modern Cottage with Pool and Garden! 8 guest - 4 bedrooms-2 baths
Interior
A Hidden Gem! Modern Cottage with Pool and Garden! 8 guest - 4 bedrooms-2 baths
2.0 star property
A Hidden Gem! Modern Cottage with Pool and Garden! 8 guest - 4 bedrooms-2 baths
Beachfront Romance: Rustic Home w/ Private Beach
On the beach
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (44)
"Relaxing stay in quiet beach town not far from home."
Beachfront Romance: Rustic Home w/ Private Beach
Designer cottage with amazing view, serene deck & outdoor shower - walk to beach
Fridge, microwave, oven, stovetop
Designer cottage with amazing view, serene deck & outdoor shower - walk to beach
9.6 out of 10, Exceptional, (21)
"We absolutely loved our stay at huron hideaway! The house was spotless upon our arrival, the decor was beautiful and we felt relaxed and right at home the minute we stepped in. The proximity to the beach was perfect!! We absolutely will be back!!"
Designer cottage with amazing view, serene deck & outdoor shower - walk to beach
Bay Shore Vacation Rental ~ 7 Mi to the Beach
House (1 Bedroom) | Private kitchen | Microwave, blender, cookware/dishes/utensils, paper towels
Bay Shore Vacation Rental ~ 7 Mi to the Beach
3.0 star property
10.0 out of 10, Exceptional, (1)
Bay Shore Vacation Rental ~ 7 Mi to the Beach
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
Beach nearby, sun loungers
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
9.8 out of 10, Exceptional, (6)
"Owner was extremely attentive and friendly. Left groceries on the front porch the next morning and made an excellent dinner recommendation. It is a lovely cottage within a pleasant walking distance to the beach. Owner offered meticulous attention to detail and decor. Very clean. Highly recommended. "
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
Luxury Beach Cottage: Wineries, Shopping & The Hamptons
Property grounds
Luxury Beach Cottage: Wineries, Shopping & The Hamptons
10.0 out of 10, Exceptional, (25)
"A wonderful home, incredible location, views breathtaking"
Luxury Beach Cottage: Wineries, Shopping & The Hamptons
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Property grounds
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
9.8 out of 10, Exceptional, (19)
"Everything about this stay was wonderful, Sandy and John were lovely hosts, the grounds and location absolutely beautiful and a "labor of love" clearly. Our pup was totally welcomed and we equally enjoyed being on the property on the screened in porch or outside grilling and visiting the area, neighboring towns and the vineyards. For a family of four this is great, or also a few groups of friends renting the cottages also would be nice. Thank you to Sandy and John and we will look forward to...
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
THE SURF SHACK "A WAVE FROM IT ALL"
Beach nearby, sun loungers
THE SURF SHACK "A WAVE FROM IT ALL"
9.6 out of 10, Exceptional, (23)
"Such a cute neighborhood and friendly neighbors! room to enjoy time together in the open concept, and the great back deck!!! would definitely stay here again if I'm in this area. Thank you!"
THE SURF SHACK "A WAVE FROM IT ALL"
Charming Rocky Point Home ~ 1 Mi to Beach!
House (3 Bedrooms) | Private kitchen | Dishwasher, paper towels
Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Charming Rocky Point Home ~ 1 Mi to Beach!
1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
2 bedrooms, travel crib, free WiFi, bed sheets
1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
9.4 out of 10, Exceptional, (6)
"Everything was excellent"
1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Fridge, microwave, stovetop, dishwasher
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
8.0 out of 10, Very Good, (3)
"We had family stay here, one set of family left early in the morning and another later. The owner, who lives in the basement, woke up those staying here on their last day at 4:30 in the morning attempting to get in the house thinking we all had left. Scared my family half to death! Check-out time was not honored. Awful stay with nosy owner creeping around everywhere!"
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Amazing Rocky Point Retreat Overlooking the Sound!
Interior
Amazing Rocky Point Retreat Overlooking the Sound!
3.0 star property
Amazing Rocky Point Retreat Overlooking the Sound!
Waterfront Home w/ Large Deck & Dock on Narrow Bay
Interior
Waterfront Home w/ Large Deck & Dock on Narrow Bay
3.0 star property
Waterfront Home w/ Large Deck & Dock on Narrow Bay
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Towels
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
10.0 out of 10, Exceptional, (12)
"Great place. Amazing kayaking. Gorgeous garden"
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
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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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Other property types in Middle Island

Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
Interior
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
7.0 out of 10, Good, (20)
"The house fit our needs. Fun was had on the quad. A real ladder to the treehouse. On the fridge the water and ice maker doesn't work. It was nice to be able to sit out on the swing and also in the back of the house too. the short walk to the little lake was pretty. Response with property manager was good, and refurbished the paper supplies we needed for the house in less than hour. It was a nice 2 night stay."
The price is $1,028
includes taxes & fees
$1,028 per night
Sep 27 - Sep 28
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
Gorgeous NEW East End cottage along water! Minutes from Hamptons and wineries!
Smart TV, fireplace, video games, stereo
Gorgeous NEW East End cottage along water! Minutes from Hamptons and wineries!
10.0 out of 10, Exceptional, (73)
"We were there just for one night and didn't get to spend enough time at the house. Wish it could have been longer! This was a beautiful property. The house is amazing. Will come back again."
The price is $372
includes taxes & fees
$372 per night
Oct 2 - Oct 3
Gorgeous NEW East End cottage along water! Minutes from Hamptons and wineries!
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.2 out of 10, Wonderful, (15)
"We stayed here for one night & it was perfect! Husband is usually standoff-ish to “stay in someone’s house” but this bedroom/bathroom was completely private, including private fencing. The host sent us detailed information the day of regarding parking & misc info. TV in the room as well, so that was a perk. There’s also a keurig if you wanted to bring your own k-cups. Overall it was clean, simple, and way more promising than having stayed at a hotel for more space. Even the location it’s in was...
The price is $148
includes taxes & fees
$140 per night
Sep 29 - Sep 30
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
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.

Frequently asked questions

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