Search Cottages in Middle Island

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 51 Cottages in Middle Island with updated reviews, rates, and availability.

Poppys Private Beach Paradise: Wading River, Northfork
Panoramic view at Poppy's Private Beach Paradise

Poppys Private Beach Paradise: Wading River, Northfork

10.0 out of 10, Exceptional, (3)
"On Long Island for a wedding. We enjoyed the stay, it was clean and bright. Property manager was VERY responsive. Would highly recommend!!! "
Poppys Private Beach Paradise: Wading River, Northfork
Cozy Country Cottage #4
Property grounds

Cozy Country Cottage #4

10.0 out of 10, Exceptional, (3)
"Rob was great. The neighborhood was great. The house was great. If you are a baseball player, you'll love this place! Will return."
Cozy Country Cottage #4
Charming and Bright Cottage with Salt Water Pool
Pool

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
Beachfront Romance: Rustic Home w/ Private Beach
A cozy home by the sea!

Beachfront Romance: Rustic Home w/ Private Beach

9.2 out of 10, Wonderful, (46)
"We were looking for a small and private beach house getaway for the weekend and found this hidden gem. Our property manager, Debbie, made herself available throughout our stay to answer all of our questions. Everything needed for our comfort weekend was provided. We strongly recommend this place for those who are looking to get away from the hustle and bustle of city life. We will be returning! "
Beachfront Romance: Rustic Home w/ Private Beach
Designer cottage with amazing view, serene deck & outdoor shower - walk to beach

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
Cozy Country Cottage #3
private 2 car driveway. on a private country road

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (13)
"Very nice area. Clean and comfortable place"
The price is SAR 563
SAR 1,071 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Country Cottage #3
Charming Patchogue Cottage!!!
Living area

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!!!
Bay Shore Vacation Rental ~ 7 Mi to the Beach
Living area

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!
The BEACH! THIS is what folks come here for! The BHCC is an added amenity.

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!
Cozy Country Cottage #2
entrance to cottage number 2

Cozy Country Cottage #2

7.4 out of 10, Good, (6)
"I booked this property as I was running my first 50-mile race and it was located within 2 miles from the starting trailhead! I wanted a place close by that was big enough to house 4 people total and this cottage provided exactly that. The pictures don’t do it justice truthfully as it was much bigger than I thought it was going to be. The house was very cozy and welcoming, and provided everything I needed for a weekend away. I will definitely book it again! "
The price is SAR 601
SAR 1,116 total
includes taxes & fees
5 Jan - 6 January 2025
Cozy Country Cottage #2
Luxury Beach Cottage: Wineries, Shopping & The Hamptons
Outdoor seats and grill at the patio

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"
MASTER BEDROOM BATHROOM AMENITIES

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!
Exterior

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
Exterior

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!
Commack Vacation Rental | 3BR | 1BA | 1,300 Sq Ft | 3 Steps Required for Access

Quiet Commack Cottage w/ Pool, 8 Mi to Beach!

8.6 out of 10, Excellent, (4)
"We felt very cozy in the home. We were comfortable letting our dogs run around the back yard. Excellent location to all our favorite places. We will stay again. "
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Amazing Rocky Point Retreat Overlooking the Sound!
Exterior

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
Dining

Waterfront Home w/ Large Deck & Dock on Narrow Bay

3.0 star property
Waterfront Home w/ Large Deck & Dock on Narrow Bay
Cozy Riverside Cottage
Exterior

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

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
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.
Don't see what you're looking for?
See all available properties in Middle Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middle Island

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

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

9.4 out of 10, Exceptional, (19)
"I really enjoyed my stay. It was convenient and exceeded my expectations. When I am in town again I will definitely book again."
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Heated 40ft saline pool and deck in separate secure fenced area with all day sun

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (167)
"Group of 6 women getting together. Beautiful spacious home. We all had our own bedrooms. Having 4.5 baths was great. Plenty of space for all of us. Host was excellent and had great recommendations. Quick ride to the beautiful beach. "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
5 bedroom Private Family Get Away w/ Heated Pool
heated in deck pool, plenty of floats and pool toys

5 bedroom Private Family Get Away w/ Heated Pool

10.0 out of 10, Exceptional, (13)
"We were a group age 3 to 75! The house was clean, well stocked and things for everyone’s interest. Our host, Carrie, was kind and responsive. It will be a beautiful memory of spending time with our children and grandchildren. "
5 bedroom Private Family Get Away w/ Heated Pool
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

Why book your cottage in Middle Island with Expedia?
Reserving a cottage in Middle Island is as easy as clicking on your travel dates and picking your ideal place for outdoor relaxation and recreation. From upscale retreats to low-cost properties and cottages that include perks like a hot tub, Expedia has something for all traveler tastes. As for the best offers around? We’ve got them as well!
How can I find cheap cottages in Middle Island?
With Expedia’s handy filter tool, sourcing cheap cottages in Middle Island is a snap. To view properties that are friendly on the wallet, fine-tune your search results by budget, amenities and star rating.