
Holiday houses in Head of the Harbor
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Top-rated holiday rentals in Head of the Harbor
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Head of the Harbor
Superhost

Apartment in Downtown Stamford
4.83 out of 5 average rating, 6 reviewsSunny 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 reviewsA-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 reviewsSeaside 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 reviewsHome 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 reviewsHamptons 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 reviewsGreat 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 reviewsSweet & 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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- Radio City Music Hall
- Beach
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Jones Beach
- Barclays Center
- Tenement Museum
- Fairfield Beach
- Riverside Park
- Southampton Beach
- Rye Beach
- Yale University
- Comedy Cellar
- Apollo Theater
- Gilgo Beach
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- Rye Playland Beach
- MetLife Stadium