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Our top choices for Middle Island vacation homes
3 Story Beach Waterview, 3 KING bed, golf putting green!
3 Story Beach Waterview, 3 KING bed, golf putting green!Shirley
10.0 out of 10, Exceptional, (22)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
Red F.
$546 nightly
The price is $624
Dec 30 - Dec 31
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.Brentwood
9.4 out of 10, Exceptional, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
Sophie B.
$144 nightly
The price is $165
Dec 27 - Dec 28
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Spacious multiples bedroom house in enchanting Calverton with WiFi, ACCalverton
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
Nicole A.
$582 nightly
The price is $665
Dec 24 - Dec 25
Total with taxes and fees
Peaceful private 2-bedroom house in Bayport.Amazing location!
Peaceful private 2-bedroom house in Bayport.Amazing location!Bayport
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
Emily D.
$195 nightly
The price is $223
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hottub, ⛳️, htd pool, Sauna, Basketball
Hottub, ⛳️, htd pool, Sauna, BasketballMastic
10.0 out of 10, Exceptional, (27)
"Excellent accommodations for a large family gathering.The home is inviting and comfortable. It offers many amenities and the host is very hospitable. "
Maria C.
$1,611 nightly
The price is $1,841
Dec 30 - Dec 31
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NYRocky Point
10.0 out of 10, Exceptional, (23)
"Pet friendly "
Steven
$463 nightly
The price is $529
Jan 1 - Jan 2, 2026
Total with taxes and fees
Modern Vacation home. Close to The Hamptons
Modern Vacation home. Close to The HamptonsShirley
10.0 out of 10, Exceptional, (4)
"5/5 I enjoyed my stay , very clean and spacious. "
Quywana F.
$520 nightly
The price is $594
Jan 4 - Jan 5, 2026
Total with taxes and fees
$730 nightly
The price is $834
Jan 5 - Jan 6, 2026
Total with taxes and fees
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
Home2 Suites by Hilton Long Island Brookhaven
10/10 Excellent
Find out more about Middle Island
Middle Island Vacation Homes information
Number of reviews | 143 |
|---|---|
Accommodation | 550 Vacation Homes |
Lowest Price | $165 |
Highest Price | $2,193 |
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