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Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Head of the Harbor vacation rentals

1 bedroom, desk, iron/ironing board, free WiFi

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is ￥17,678
￥31,196 total
includes taxes & fees
Jul 13 - Jul 14
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Terrace/patio

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (6 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is ￥11,266
￥46,674 total
includes taxes & fees
Jul 23 - Jul 24
The Royal Suite - Ronkonkoma
Deluxe Apartment, Non Smoking, Private Bathroom | Interior

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is ￥21,933
￥49,144 total
includes taxes & fees
Jul 15 - Jul 16
Sundown Escape-South Shore Long Island
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (45 reviews)
"This place was the perfect location for us. Almost exact center between Jones beach and Port Jefferson. Clean and identical to what is shown."
United States
Marcus
The price is ￥16,094
￥26,749 total
includes taxes & fees
Jul 12 - Jul 13
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (55 reviews)
"I love the layout of this apt. Perfect for 2 to 3 people, it was clean and nothing out of place. The host was great and communicated well. I will be looking for this place again next year."
United States
Shamel
The price is ￥13,785
￥23,759 total
includes taxes & fees
Jul 10 - Jul 11
Business or Weekend escape
1 bedroom, iron/ironing board, free WiFi, bed sheets

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (7 reviews)
"The whole experience was great"
United States
David
The price is ￥17,224
￥34,503 total
includes taxes & fees
Jul 16 - Jul 17
Your Perfect Getaway Between Farmingdale & Amityville
Interior

Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (27 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is ￥23,410
￥41,049 total
includes taxes & fees
Jul 15 - Jul 16
Private 1 bedroom apt in a quiet neighborhood, close to all!
Classic Suite | Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (98 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is ￥29,825
￥44,216 total
includes taxes & fees
Aug 4 - Aug 5
DUNE Fairfield Beach
Exterior

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (23 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is ￥19,705
￥29,000 total
includes taxes & fees
Jul 13 - Jul 14
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Private kitchen

Elite room stay

Elite room stay
Bridgeport
The price is ￥33,571
￥55,311 total
includes taxes & fees
Jul 14 - Jul 15
Elite room stay
Interior

Cozy Country Cottage #4

Cozy Country Cottage #4
Miller Place
9.6 out of 10, Exceptional, (16 reviews)
"Great stay"
United States
Susan W.
The price is ￥30,814
￥61,331 total
includes taxes & fees
Aug 7 - Aug 8
Cozy Country Cottage #4
TV, fireplace

59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV

59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV
South End
8.0 out of 10, Very Good, (8 reviews)
"A very convenient location, only a 5 minute walk to the beach. It is also a safe area as well. The property itself has all of the necessities for a long term stay such as a private bathroom with a shower and a private kitchen. It is also not far from the downtown Bridgeport area with many places worth visiting."
United States
Sam S.
The price is ￥23,281
￥42,418 total
includes taxes & fees
Jul 10 - Jul 11
59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV
1 bedroom, free WiFi, bed sheets

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (5 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is ￥21,947
￥36,591 total
includes taxes & fees
Jul 12 - Jul 13
South Shore Studio in Mastic
Fridge, microwave, oven, stovetop

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (4 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is ￥28,581
￥63,155 total
includes taxes & fees
Jul 12 - Jul 13
Modern 2 Bed in BlackRock
1 bedroom, WiFi, bed sheets

1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (23 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is ￥19,021
￥32,318 total
includes taxes & fees
Jul 13 - Jul 14
1 bedroom 1 bath private entrance
1 bedroom, iron/ironing board, free WiFi, bed sheets

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is ￥30,003
￥60,405 total
includes taxes & fees
Jul 13 - Jul 14
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Fridge, microwave, coffee/tea maker, electric kettle

Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is ￥23,354
￥55,565 total
includes taxes & fees
Jul 16 - Jul 17
Sundown Escape Near SouthShore University Hospital
TV

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is ￥18,245
￥55,678 total
includes taxes & fees
Jul 14 - Jul 15
Spacious one Bedroom Apt with private entrance
Fridge, microwave, oven, stovetop

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
The price is ￥26,161
￥57,397 total
includes taxes & fees
Jul 14 - Jul 15
Renovated 2BR Retreat / Modern Comforts Included
Interior

Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is ￥28,382
￥43,544 total
includes taxes & fees
Aug 7 - Aug 8
Cozy king suite with kitchen and dining area.
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

Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

10/10 Excellent
"My overall experience is always exceptional"
Michelle 1-night trip
Posted 11 hours ago
Jake's 58 Casino Hotel - Adult Only

Find out more about Head of the Harbor

Search for holiday rentals in Head of the Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Head of the Harbor using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Head of the Harbor?

Yes, we offer vacation rentals close to top attractions in Head of the Harbor, or you can choose a more remote option if you'd like a relaxing place to stay. Head of the Harbor is known for its wineries and parks.

What are some of the best vacation rentals that Head of the Harbor has to offer?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This vacation home rental near Head of the Harbor has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

What can I see and do in Head of the Harbor?

Explore the area and family-friendly sights such as Vanderbilt Museum, or get out into nature at a spot like Avalon Park and Preserve. Other places in town to visit include Harmony Vineyards and Stony Brook Grist Mill.

What are vacation rentals like in Head of the Harbor?

Vacation rentals are private accommodations you can reserve for several days or longer in Head of the Harbor. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family gatherings.