Holiday houses in Head of the Harbor

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Popular amenities for Head of the Harbor holiday rentals

Stay near Head of the Harbor's top sights

Smith Haven Mall25 locals recommend
Stony Brook Village Center5 locals recommend
Harmony Vineyards6 locals recommend
The Long Island Museum8 locals recommend
Crazy Beans4 locals recommend
Whisper Vineyards5 locals recommend

Other great holiday rentals in Head of the Harbor

Superhost
Apartment in Downtown Stamford
4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars4 months ago
Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit
Superhost
Cabin in Shirley
4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

JenniferRating, 5 stars2 weeks ago
Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!
Guest favourite
Cottage in Norwalk
4.94 out of 5 average rating, 68 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars2 weeks ago
We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!
Superhost
Apartment in Brentwood
4.84 out of 5 average rating, 32 reviews

Home away your home

GeraldineRating, 5 stars1 week ago
Nice place exactly what the pictures show .. Super nice host.. but if you are looking for a quiet place. This place is definitely not it. You can hear every move and every sound from the people that live upstairs last night we spent a good few hours hearing a baby cry. Also they have the children’s toys such as a trampoline up against the window of the unityou do park on the street and the owner or tenants whoever lives upstairs parks in the driveways. it’s a very tight walk in between cars in the driveway because they do park a lot of cars in the driveway side-by-side.
Top Guest favourite
Cottage in Guilford
4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

MaryRating, 5 stars3 weeks ago
My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!
Guest favourite
Home in Hampton Bays
4.89 out of 5 average rating, 100 reviews

Hamptons Escape minutes from Beaches and Nightlife

EricaRating, 5 stars1 week ago
Our family spent a great weekend here. There was plenty of rooms for everyone to have their own, and everything was clean, cozy, and comfortable. The home was exactly as shown in the pictures and everything we could have needed was there. The hot tub was lovely both nights, and the pool area looks pretty though was not yet opened for the season. This is a perfect spot to bring your family, to relax, and enjoy all that the Hamptons, and Hampton Bays has to offer. We hope to return soon!
Guest favourite
Cabin in Rocky Point
4.89 out of 5 average rating, 486 reviews

Great little place just for a couple

MeganRating, 5 stars1 day ago
A wonderful spot and wonderful host. Everything was cheery and thoughtfully done. I knocked off a star for the price mostly because I wasn't anticipating how expensive it is to get around by Uber in the area, and to find an accessible grocery store - otherwise necessary to have a car. Ended up ordering UberEats... my mom was at another Airbnb down the road and the difference in how we were treated as guests was astronomical. Marina did not charge me for having my little dog, there was a little firewood for us to use, fresh coffee and tea, and all the amenities! Marina was also very responsive and kind, and left a very helpful note about whether the beach is public or not. 100% recommend. In contrast, my mom felt badly treated by the host, the place was poorly kept and she felt it was way overpriced in comparison to mine (Marina's). Good thing she was able to come here during the day, and we spent most of our time here, in the yard or the short walk to the beach.
Guest favourite
Home in Yonkers
4.96 out of 5 average rating, 24 reviews

Sweet & cozy house

AndyRating, 5 stars1 week ago
A wonderful place to stay with family. Clean and spacious, lots of amenities and extras with the place. Felt right at home, miles better than a hotel. Would recommend if you're looking for a comfortable and wonderful stay.

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