Holiday Rentals in Middle Island

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Holiday Rentals in Middle Island

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

9.4 out of 10, Exceptional, (29)
"its small but very nice for a short stay would recommend."
The price is €145
includes taxes & fees
12 Oct - 13 Oct
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (20)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (71)
"Very nice place for a family to stay"
The price is €1,038
includes taxes & fees
11 Oct - 12 Oct
Newly Renovated Luxury Beach House Ocean Bay Park

Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

9.0 out of 10, Wonderful, (18)
"The property was very quaint and comfortable. We'll probably stay again in the future"
The price is €133
includes taxes & fees
10 Oct - 11 Oct
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

Tiny Home Private, Students, Nurses, Tech

9.0 out of 10, Wonderful, (4)
"We wanted an inexpensive place to stay out on Long Island for July 4th weekend. We were a 15-20 minute drive to the beautiful beaches of Robert Moses and a 2 hour drive from Montauk.We were able to stay for a very reasonable price over a notoriously expensive weekend.Jenelle's communication was direct, welcoming and helpful.We would definitely stay here again!"
The price is €188
includes taxes & fees
10 Oct - 11 Oct
Tiny Home Private, Students, Nurses, Tech

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

10.0 out of 10, Exceptional, (102)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is €650
includes taxes & fees
2 Nov - 3 Nov
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"Stay away"
The price is €244
includes taxes & fees
14 Oct - 15 Oct
Walk to Beach 2BR Near Dining & Shopping

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is €566
includes taxes & fees
12 Oct - 13 Oct
Modern Vacation home. Close to The Hamptons

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (191)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is €1,122
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Beautiful historic home in Stony Brook!

2.0 star property
8.4 out of 10, Very good, (15)
"Was a great place is a small town. Everything was clean and nice just wish there was a small sheer curtain in the bathroom where you shower. "
Beautiful historic home in Stony Brook!

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is €805
includes taxes & fees
10 Oct - 11 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

9.0 out of 10, Wonderful, (32)
"This is a charming little guest house that allows dogs and is steps away from the beach. What more can I say…"
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

9.0 out of 10, Wonderful, (53)
"Has a very nice stay."
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (50)
"The place was lovely and well appointed.. Beds were comfy. The spiral staircase was a bit tight to maneuver but location was perfect. It was a great spot for us, close to family in Sound Beach and Miller Place."
1856 Trading House w/ walk to water

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (7)
"What a nice place to stay! Key code entry, clean, quiet, comfortable and spacious. This basement apartment exceeded expectations and met all our needs. We would definitely rent this space again."
The price is €157
includes taxes & fees
22 Oct - 23 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

9.6 out of 10, Exceptional, (23)
"This was the perfect location to enjoy the vineyards for my friend’s bachelorette party. Everyone had a comfy room and the space was very generous. Additionally the yard was massive and had ample seating. We had a great time and would definitely recommend this to all!"
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Summer getaway

9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Summer getaway

Tranquil Stay

10.0 out of 10, Exceptional, (6)
"Great stay with family to see a couple of our son's shows at the Gateway Theatre. Thank you Andre for be a great host...!!!"
The price is €493
includes taxes & fees
22 Oct - 23 Oct
Tranquil Stay

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.4 out of 10, Exceptional, (41)
"I went with family for a memorial celebration for a family member who had passed away. Worked out great and enjoyed the back deck & fire pit! Also, beds were comfy and open kitchen & LR were great for entertaining! Thank you Billy:)"
The price is €326
includes taxes & fees
15 Oct - 16 Oct
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
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

Find out more about Middle Island

Find out more about Middle Island

Everything you need to know about Middle Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middle Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middle Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middle Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middle Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middle Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middle Island holiday rentals we have selected for you start as low as €133 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middle Island rentals

At Expedia, we put the best Middle Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middle Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middle Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middle Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Middle Island?

Yes, there are holiday rentals close to the most popular sights in Middle Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middle Island has to offer?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This holiday home rental outside of Middle Island has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

What can I see and do in Middle Island?

While exploring the area, visit family-friendly sights like Long Island Game Farm, or get outside and enjoy nature at Carmans River. Brookhaven National Laboratory and Lasorda Legacy Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Middle Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middle Island. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.