Head of the Harbor Vacation Rentals
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Vacation Rentals in Head of the Harbor
Charming Home in Seaside
Bridgeport CT
With a stay at this vacation home in Bridgeport (South End), you'll be steps from University of Bridgeport and Seaside Park.
Washer
Dryer
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Centereach NY
With a stay at this vacation home in Centereach, you'll be within a 5-minute drive of Stony Brook University and Smithaven Mall.
Washer
Dryer
Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor NY
$411 nightly
The price is $470 total per night
$470 total
Dec 8 - Dec 9
Total with taxes and fees
A stay at this vacation home places you in the heart of Cold Spring Harbor, within a 15-minute walk of Cold Spring Harbor State Park and Cold Spring Harbor Whaling Museum and Education Center.
Kitchen
Washer
Stareway to Heaven Su
Fairfield CT
With a stay at this vacation home in Fairfield, you'll be by the sea, just a 2-minute walk from South Pine Creek Beach and 8 minutes by foot from Pine Creek Par 3 Golf Course.
Kitchen
Washer
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
Fairfield CT
With a stay at this vacation home in Fairfield, you'll be by the sea, just a 4-minute walk from South Benson Marina and 11 minutes by foot from Fairfield Museum and History Center.
Kitchen
Washer
Business or Weekend escape
Stratford CT
$130 nightly
The price is $147 total per night
$147 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.
Pool
Air conditioning
LUXURY BAY SHORE HOME
17 Mowbray Ave Bay Shore NY
With a stay at this vacation home in Bay Shore, you'll be within a 5-minute walk of Gilgo State Park and South Shore University Hospital.
Pet friendly
Parking included
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood NY
$144 nightly
The price is $165 total per night
$165 total
Dec 8 - Dec 9
Total with taxes and fees
Located in Brentwood, this vacation home is within a 5-minute drive of Hauppauge Industrial Park and Nissequogue River.
Pet friendly
Free WiFi
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Northport NY
When you a stay at this vacation home in Northport, you'll be on the beach, within a 5-minute walk of Cow Harbor Park and Northport Village Park.
Hot Tub
Kitchen
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc
Islip NY
Located in Islip, this vacation home is within a 5-minute drive of Bethpage Ballpark and Cohalan Court Complex.
Kitchen
Washer
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See all available properties in Head of the Harbor
View all propertiesLowest 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.
Head of the Harbor Vacation Rentals essential information
Accommodation | 503 Vacation Rentals |
|---|---|
Lowest Price | $147 |
Highest Price | $470 |
Popular accommodation | Charming Home in Seaside, Cozy 4-bedroom house with AC and WiFi in Centereach, New York. , Captain's Cottage - Cold Spring Harbor Water Views, Stareway to Heaven Su, Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train , Business or Weekend escape, LUXURY BAY SHORE HOME, Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. , Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC, fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc, Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs, Spacious Gorgeous Getaway perfect for family reunion or business |