Head of the Harbor Vacation Rentals

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Browse Select Head of the Harbor Vacation Homes

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

9.4 out of 10, Exceptional, (26)
"its small but very nice for a short stay would recommend."
The price is CA $136
CA $226 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (67)
"Very nice place for a family to stay"
The price is CA $961
CA $1,722 total
includes taxes & fees
Oct 2 - Oct 3
Newly Renovated Luxury Beach House Ocean Bay Park

Charming 3-bedroom modern family retreat!

10.0 out of 10, Exceptional, (1)
"Spacious, clean and host was very responsive to any questions we had ! "
The price is CA $474
CA $710 total
includes taxes & fees
Sep 7 - Sep 8
Charming 3-bedroom modern family retreat!

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (13)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is CA $346
CA $469 total
includes taxes & fees
Sep 9 - Sep 10
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.2 out of 10, Wonderful, (7)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
"We stayed with family at this lovely home for my son’s graduation and Mother’s Day. The home is even nicer than the pictures- everything is top notch. It’s one block from a nice beach with lovely views from many of the rooms. We would love to come back and stay! "
Stareway to Heaven Su

Business or Weekend escape

9.2 out of 10, Wonderful, (46)
"We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. "
The price is CA $117
CA $201 total
includes taxes & fees
Sep 14 - Sep 15
Business or Weekend escape

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (19)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (65)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (34)
"House was very clean and maintained. We needed to check in a day later and the host was very accommodating. Overall a great place to stay! "
Cheerful 4 bedrooms residential house.

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (66)
"Great home to stay. Beautiful area to explore!"
The price is CA $385
CA $786 total
includes taxes & fees
Sep 8 - Sep 9
Captain's Cottage - Cold Spring Harbor Water Views

Luxury and Affordable Family Home

7.0 out of 10, Good, (7)
"My family and I had the pleasure of staying here during the Christmas holidays, and it was an excellent experience. We were especially grateful for the accessibility features, as my grandmother (85 years young), who uses a walker and had recently undergone surgery, was able to comfortably stay on the main floor. The property had just a few steps to enter, and best of all, there was a bedroom and full bathroom on the main level, along with ample room for a walker or wheelchair.The home itself was...
The price is CA $631
CA $1,318 total
includes taxes & fees
Sep 6 - Sep 7
Luxury and Affordable Family Home

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

10.0 out of 10, Exceptional, (83)
"Stayed here for a family reunion. Joe has created something special. Highly recommend."
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

10.0 out of 10, Exceptional, (11)
"Very nice place close to the beach and nice restaurant. The host was very nice and did a very good banana cake."
Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (38)
"Convenient location, very clean, updated home. The online pictures are accurate, the finished basement is actually more spacious than the photos show. We enjoyed our time here, and would definitely stay again. "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Stay at Black Rock Harbor

10.0 out of 10, Exceptional, (21)
"Beautifully appointed home, comfortable furnishings, and fantastic location. We enjoyed the indoor and outdoor space, as well as the nearby beach, restaurants and freeway access. Everything was in fine working order and our stay was enjoyable! "
Stay at Black Rock Harbor

Blue Cottage East Setauket

Blue Cottage East Setauket

Bayfront Home in Patchogue w/ Deck & Fishing Dock

10.0 out of 10, Exceptional, (4)
"Excellent place and perfect location for everything. "
Bayfront Home in Patchogue w/ Deck & Fishing Dock

Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

10.0 out of 10, Exceptional, (58)
"From the moment we booked this trip we knew we were in for a treat. Windows on the Sea did not disappoint! From the early communication with our hosts and their thoughtful check-ins leading up to our trip, this was the best experience we could ask for. We highly recommend staying here!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
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 Head of the Harbor Hotel Reviews

Find out more about Head of the Harbor

Find out more about Head of the Harbor

Head of the Harbor Vacation Homes information

Number of reviews
Accommodation
503 Vacation Homes
Lowest Price
CA $117
Highest Price
CA $961

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