Search Vacation Homes in Head of the Harbor

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Our top choices for Head of the Harbor vacation homes

The Bella Vista St James! Waterfront house with a beach dock and so much more!

The Bella Vista St James! Waterfront house with a beach dock and so much more!
Saint James
10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
$1,782 nightly
The price is $2,036
Dec 14 - Dec 15
Total with taxes and fees
The Bella Vista St James! Waterfront house with a beach dock and so much more!

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
2.0 star property
Ronkonkoma
10.0 out of 10, Exceptional, (4)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
$257 nightly
The price is $294
Dec 17 - Dec 18
Total with taxes and fees
The Royal Suite - Ronkonkoma

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

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
$144 nightly
The price is $165
Dec 14 - Dec 15
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (21)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
$546 nightly
The price is $624
Dec 17 - Dec 18
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$130 nightly
The price is $147
Jan 1 - Jan 2, 2026
Total with taxes and fees
Business or Weekend escape

Hottub, ⛳️, htd pool, Sauna, Basketball

Hottub, ⛳️, htd pool, Sauna, Basketball
Mastic
10.0 out of 10, Exceptional, (27)
"Stayed here for my wedding weekends and absolutely loved the house! Very spacious and beautiful yard! Had so much fun "
United States
Tiffany I.
$971 nightly
The price is $1,109
Dec 14 - Dec 15
Total with taxes and fees
Hottub, ⛳️, htd pool, Sauna, Basketball

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

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Mastic Beach
10.0 out of 10, Exceptional, (5)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
United States
Leonid T.
$274 nightly
The price is $313
Dec 17 - Dec 18
Total with taxes and fees
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Peaceful private 2-bedroom house in Bayport.Amazing location!

Peaceful private 2-bedroom house in Bayport.Amazing location!
2.0 star property
Bayport
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
$243 nightly
The price is $278
Dec 15 - Dec 16
Total with taxes and fees
Peaceful private 2-bedroom house in Bayport.Amazing location!

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach
Fairfield
10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
$433 nightly
The price is $501
Dec 15 - Dec 16
Total with taxes and fees
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
$530 nightly
The price is $606
Dec 15 - Dec 16
Total with taxes and fees
Modern Vacation home. Close to The Hamptons

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fairfield
10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
$424 nightly
The price is $480
Jan 12 - Jan 13, 2026
Total with taxes and fees
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Stylish 2BR House Near Stony Brook University and shopping, fully renovated
2.0 star property
Stony Brook
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
$468 nightly
The price is $534
Dec 22 - Dec 23
Total with taxes and fees
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (23)
"Pet friendly "
United States
Steven
$463 nightly
The price is $529
Jan 1 - Jan 2, 2026
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Modern + Spacious 5BR/2BA Home, Renovated Backyard

Modern + Spacious 5BR/2BA Home, Renovated Backyard
West End - West Side
9.6 out of 10, Exceptional, (4)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
$682 nightly
The price is $773
Dec 14 - Dec 15
Total with taxes and fees
Modern + Spacious 5BR/2BA Home, Renovated Backyard

🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
Fairfield
10.0 out of 10, Exceptional, (1)
"The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. "
United States
Patricia B.
$1,631 nightly
The price is $1,849
Dec 14 - Dec 15
Total with taxes and fees
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

Choice home welcome to the highest rated home on every platform

Choice home welcome to the highest rated home on every platform
West Babylon
$196 nightly
The price is $224
Dec 14 - Dec 15
Total with taxes and fees
Choice home welcome to the highest rated home on every platform

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
$461 nightly
The price is $527
Jan 5 - Jan 6, 2026
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
2.0 star property
Historic District
10.0 out of 10, Exceptional, (8)
"We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful."
Canada
nawab k.
$485 nightly
The price is $550
Dec 15 - Dec 16
Total with taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
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

Head of the Harbor Vacation Homes information

Number of reviews
286
Accommodation
475 Vacation Homes
Lowest Price
$147
Highest Price
$2,036

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