Head of the Harbor Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Vacation Rentals in Head of the Harbor
Business or Weekend escape
The price is $141 per night
$141
includes taxes & fees
$125 per night
Nov 17 - Nov 18
With a stay at this vacation home in Stratford, you'll be within a 10-minute drive of Fairfield University and Perry House.
Pool
Air conditioning
Beautiful historic home in Stony Brook!
With a stay at this vacation home in Stony Brook, you'll be within a 5-minute drive of Stony Brook University and West Meadow Beach Historic District.
Washer
Dryer
Coastal Retreat: Waterfront, Deck, Awesome Views
When you stay at this vacation home in Wading River, you'll be on the beach, within a 5-minute drive of Wildwood State Park and Police Officers Memorial Park.
Kitchen
Washer
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
The price is $148 per night
$148
includes taxes & fees
$140 per night
Nov 17 - Nov 18
Located in Brentwood, this vacation home is within a 5-minute drive of Hauppauge Industrial Park and Nissequogue River.
Pet friendly
Air conditioning
3 Story Beach Waterview, 3 KING bed, golf putting green!
The price is $510 per night
$510
includes taxes & fees
$510 per night
Nov 18 - Nov 19
With a stay at this vacation home in Shirley, you'll be by the sea, a 4-minute walk from Great South Bay and a 3-minute drive from Smith Point County Park.
Kitchen
Washer
Cheerful 2-Bedroom Home With On Premises Parking
With a stay at this vacation home in Amityville, you'll be within a 10-minute drive of Bethpage Black State Park Golf Course and South Oaks Hospital.
Kitchen
Air conditioning
Stylish Sunset Retreat: Near Beach, Pool, Hot Tub
When you stay at this vacation home in Wading River, you'll be by the sea, within a 5-minute drive of Wading River Landing and Duck Pond Park.
Pool
Hot Tub
Beautiful Beach House with Large Swimming Pool in Ocean Beach
When you stay at this vacation home in Ocean Beach, you'll be by the sea, within a 10-minute walk of Ocean Beach and Great South Bay.
Pool
Kitchen
Cozy Modern Ranch House Near Bellport/Hamptons
Located in Brookhaven, this vacation home is a 4-minute drive from Great South Bay and 6 minutes from Carmans River.
Queen Vic Beach House: 5 min to Vineyards & Farmstands
Located in Wading River, this vacation home is by the ocean, within a 5-minute drive of Wading River Landing and Duck Pond Park.
Don't see what you're looking for?
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 | 364 Vacation Rentals |
|---|---|
Lowest Price | $119 |
Highest Price | $510 |
Popular accommodation | Business or Weekend escape, Beautiful historic home in Stony Brook!, Coastal Retreat: Waterfront, Deck, Awesome Views, Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. , 3 Story Beach Waterview, 3 KING bed, golf putting green!, Cheerful 2-Bedroom Home With On Premises Parking, Stylish Sunset Retreat: Near Beach, Pool, Hot Tub, Beautiful Beach House with Large Swimming Pool in Ocean Beach, Cozy Modern Ranch House Near Bellport/Hamptons , Queen Vic Beach House: 5 min to Vineyards & Farmstands, Cozy retreat with fenced in yard—centrally located in the heart of Long Island., Your home away from home |