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
Check dates for Head of the Harbor hotels
Vacation Rentals in Head of the Harbor
Business or Weekend escape
The price is $103 per night
$103
includes taxes & fees
$92 per night
Dec 24 - Dec 25
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
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa
The price is $463 per night
$463
includes taxes & fees
$396 per night
Dec 19 - Dec 20
When you stay at this vacation home in Fairfield, you'll be near the beach, within a 5-minute drive of Fairfield University and Bridgeport Downtown South Historic District.
Kitchen
Washer
Fully Renovated 4 bedroom 2 bath home in the heart of Ocean Beach
With a stay at this vacation home in Ocean Beach, you'll be near the beach, just a 3-minute walk from Great South Bay and 7 minutes by foot from Ocean Beach.
Kitchen
Washer
Cozy 3BR Near Huntington's Nightlife & Beach
Located in Huntington, this vacation home is within a 15-minute walk of AMC Shore 8 and Paramount Theater.
Kitchen
Pet friendly
3BR Paradise in Port Jefferson!
With a stay at this vacation home in Port Jefferson, you'll be within a 10-minute drive of Stony Brook University and Maritime Explorium.
Washer
Dryer
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
With a stay at this vacation home in Mastic, you'll be within a 15-minute drive of Long Island Game Farm and Carmans River.
Pool
Kitchen
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
Located in Wading River, this vacation home is on the beach, a 3-minute walk from Wading River Landing and within a 5-minute drive of Duck Pond Park.
Kitchen
Washer
Cheerful 4 bedrooms residential house.
When you a stay at this vacation home in Bridgeport, you'll be by the sea, just steps from Bridgeport Downtown South Historic District and University of Bridgeport.
Kitchen
Washer
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
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
Adorable Cottage with Water Views, Across the street from Prime & other eateries
A stay at this vacation home places you in the heart of Huntington, within a 5-minute drive of Huntington Hospital and Heckscher Museum of Art.
Kitchen
Washer
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 | 354 Vacation Rentals |
|---|---|
Lowest Price | $103 |
Highest Price | $665 |
Popular accommodation | Business or Weekend escape, Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa, Fully Renovated 4 bedroom 2 bath home in the heart of Ocean Beach, Cozy 3BR Near Huntington's Nightlife & Beach, 3BR Paradise in Port Jefferson!, 20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool., Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach, Cheerful 4 bedrooms residential house., Cozy 4-bedroom house with AC and WiFi in Centereach, New York. , Adorable Cottage with Water Views, Across the street from Prime & other eateries, Beautiful Beach House with Large Swimming Pool in Ocean Beach, Luxury and Affordable Family Home |