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Cottages in Middle Island

Our top choices for Middle Island cottages

East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!
Property grounds

East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!

10.0 out of 10, Exceptional, (98)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is SAR 806
SAR 1,911 total
includes taxes & fees
19 Oct - 20 Oct
East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!
Charming 1 bedroom Stony Brook cottage -walking distance to village & university
Exterior

Charming 1 bedroom Stony Brook cottage -walking distance to village & university

10.0 out of 10, Exceptional, (4)
"Exactly what we looking for. We loved our stay. "
Charming 1 bedroom Stony Brook cottage -walking distance to village & university
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Sun loungers, beach towels

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

9.6 out of 10, Exceptional, (40)
"Really enjoyed our stay here and had a wonderful time exploring the area."
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Charming Beach Cottage, Steps to Beach, Enjoy Harvest Time LI's Wine Region.
Exterior

Charming Beach Cottage, Steps to Beach, Enjoy Harvest Time LI's Wine Region.

10.0 out of 10, Exceptional, (2)
"The little cottage in quaint Jamesport was perfect! Felt like you were back in simpler times and able to walk to near restaurants/ beach. Joe was always responsive with all questions. Hope to visit again soon! "
Charming Beach Cottage, Steps to Beach, Enjoy Harvest Time LI's Wine Region.
Cozy Country Cottage #4
Exterior

Cozy Country Cottage #4

10.0 out of 10, Exceptional, (10)
"Very calming property and everything you would need inside. "
The price is SAR 563
SAR 1,221 total
includes taxes & fees
24 Oct - 25 Oct
Cozy Country Cottage #4
The Little Red Cottage - A cozy home steps away from private beach & wine trail.
Terrace/patio

The Little Red Cottage - A cozy home steps away from private beach & wine trail.

2.0 star property
9.4 out of 10, Exceptional, (3)
"We had such a wonderful time during our stay, thanks to Sandra's excellent hospitality. She was extremely helpful, knowledgable, and accommodating throughout our entire stay. Upon checking in, we found a beautiful welcome card and local treats left for us alongside an incredibly informative binder detailing any and all information relevant to the property, attractions in town, and fabulous restaurant recommendations. Sandra's cottage was comfortable, cozy, safe, and tidy. We are very grateful to...
The Little Red Cottage - A cozy home steps away from private beach & wine trail.
Bay Shore Vacation Rental ~ 7 Mi to the Beach
House (1 Bedroom) | Interior

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
Amazing Rocky Point Retreat Overlooking the Sound!
House (3 Bedrooms) | Interior

Amazing Rocky Point Retreat Overlooking the Sound!

3.0 star property
Amazing Rocky Point Retreat Overlooking the Sound!
Cozy Country Cottage #3
Exterior

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (27)
"Very clean and comfortable "
Cozy Country Cottage #3
Cozy Country Cottage #2
Property grounds

Cozy Country Cottage #2

8.8 out of 10, Excellent, (12)
"Cottage was awesome!! It was clean and welcoming. We felt at home. Great place to stay."
Cozy Country Cottage #2
Bayfront Home in Patchogue w/ Deck & Fishing Dock
House (3 Bedrooms) | Interior

Bayfront Home in Patchogue w/ Deck & Fishing Dock

3.0 star property
Bayfront Home in Patchogue w/ Deck & Fishing Dock
Waterfront Home w/ Large Deck & Dock on Narrow Bay
House (3 Bedrooms) | Interior

Waterfront Home w/ Large Deck & Dock on Narrow Bay

3.0 star property
Waterfront Home w/ Large Deck & Dock on Narrow Bay
Charming Rocky Point Home ~ 1 Mi to Beach!
House (3 Bedrooms) | Interior

Charming Rocky Point Home ~ 1 Mi to Beach!

3.0 star property
Charming Rocky Point Home ~ 1 Mi to 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!

9.0 out of 10, Wonderful, (10)
"Great location near good dining options (Cooperage, Desmond's), vineyards, walk to beach. Comfortable bed. It's a cabin in the woods so damp and musty smell, like a cabin in the woods."
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
Idyllic Cozy Cottage in Davis Park, Fire Island - Weekly Rentals Now Available!
Exterior

Idyllic Cozy Cottage in Davis Park, Fire Island - Weekly Rentals Now Available!

9.0 out of 10, Wonderful, (2)
"It was everything my heart desired. My mind remembered & MY SPIRIT needed to sore Looking forward to revisiting as soon as I can get my dates "
Idyllic Cozy Cottage in Davis Park, Fire Island - Weekly Rentals Now Available!
A Hidden Gem! Cozy Cottage with huge Pool & Garden! 8 guest - 4 bedrooms-2 baths
Property grounds

A Hidden Gem! Cozy Cottage with huge Pool & Garden! 8 guest - 4 bedrooms-2 baths

2.0 star property
10.0 out of 10, Exceptional, (6)
"The pictures do not do this cottage justice. The Christmas decorations were a great surprise too. Plenty of room for all 8 of us with everything we need nearby. "
A Hidden Gem! Cozy Cottage with huge Pool & Garden! 8 guest - 4 bedrooms-2 baths
Classy Getaway w/ Deck & Yard < 1 Mi to Beach
House (4 Bedrooms) | Interior

Classy Getaway w/ Deck & Yard < 1 Mi to Beach

3.0 star property
Classy Getaway w/ Deck & Yard < 1 Mi to Beach
Waterfront Home w/ Large Deck + Private Pool!
Interior

Waterfront Home w/ Large Deck + Private Pool!

3.0 star property
Waterfront Home w/ Large Deck + Private Pool!
Waterfront Beach Cottage Overlooking Long Island Sound – Baiting Hollow
Outdoor dining

Waterfront Beach Cottage Overlooking Long Island Sound – Baiting Hollow

10.0 out of 10, Exceptional, (45)
"Adorable house with everything we needed. The owners went above and beyond to make sure we enjoyed our stay!"
Waterfront Beach Cottage Overlooking Long Island Sound – Baiting Hollow
5 houses from the beach, and 5 minutes from town -- Ocean Beach 3-BR hideaway
Property grounds

5 houses from the beach, and 5 minutes from town -- Ocean Beach 3-BR hideaway

2.0 star property
10.0 out of 10, Exceptional, (1)
5 houses from the beach, and 5 minutes from town -- Ocean Beach 3-BR hideaway
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

10/10 Excellent
"The service "
Jennifer 2-night trip
Posted 3 days ago
Jake's 58 Casino Hotel - Adult Only

Frequently asked questions

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