Search for vacation rentals in Glen Head.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Glen Head area to find the perfect spot for your vacay.

4 Valentine Farm Ct

4 Valentine Farm Ct

Glen Head, NY
$25
Vacation Rentals, Unknown
Old Brookville. This gated 3+ acre estate is not your everyday listing. Built for the luxurious entertainer in you, let the plush landscaping and gardens capture you and your guests. Nestled on a......

255 Piping Rock Rd

255 Piping Rock Rd

Glen Head, NY
$20
Vacation Rentals, Unknown
Welcome to your dream rental property at 255 Piping Rock Rd! This stunning residence boasts a modern design, situated on flat land in a prime location that offers convenience and luxury. With 5......

27 Chicken Valley Rd

27 Chicken Valley Rd

Glen Head, NY
$2,100
Vacation Rentals, Unknown
Secluded 1 BR Cottage with Kitchen/Living Room Combo, separate Bedroom,Full Bath and Enclosed Porch....

144 Glen Head Rd

144 Glen Head Rd

Glen Head, NY
$3,900
Vacation Rentals, Unknown
Charming Home With Hardwood Floors And 2 Full Baths. Off Street Parking, Near Train And Shopping. Washer And Dryer, 1 Month Security And 1 Months Broker Fee Tenant Pays Own Gas Electric And Water....

6 White Gate Dr

6 White Gate Dr

Glen Head, NY
$24
Vacation Rentals, Unknown
Welcome to this stunning rental property located in Old Brookville. This stately brick colonial is proudly situated on 3 acres. The 10-room, 6600 sq. ft. home is truly a masterpiece. The spacious......

0 Glen Head Rd

0 Glen Head Rd

Glen Head, NY
$2,950
Vacation Rentals, Unknown
All New Apartment With Open Feel Living Room Picture Coming Soon. Open Kitchen With Island Granite Counter Tops. Large Bedrooms Plenty Of Storage, Off Street Parking, Near Village Train And......

60 Piping Rock Rd

60 Piping Rock Rd

Glen Head, NY
$35
Vacation Rentals, Unknown
Avail for minimum of 6 months, 1-2 years: GRAY HORSE FARM: This magnificent iconic estate on desirable Piping Rock Road is situated on 9 flat acres and offers 13,324 square feet of luxe living plus......

75 Plymouth Dr N

75 Plymouth Dr N

Glen Head, NY
$5,400
Vacation Rentals, Unknown
3 Bedroom 2 Bathroom Ranch In North Shore School District. Sun Drenched Newly Renovated Entire House Rental. Open Lay Out, Easy Access To Yard From Living Room And Kitchen, Well Maintained Wood......

60 Piping Rock Rd

60 Piping Rock Rd

Glen Head, NY
$35
Vacation Rentals, Unknown
Introducing GRAY HORSE FARM: This magnificent iconic estate on desirable Piping Rock Road is situated on 9 flat acres and offers 13,324 square feet of luxe living plus beautiful apartments,......

2 Elm Pl

2 Elm Pl

Glen Head, NY
$4,500
Vacation Rentals, Unknown
Welcome to Glen Head, where an exceptional opportunity awaits you in this distinguished residence situated within a prime location and nestled on a tranquil cul-de-sac. Ideally located in the......

6 White Gate Dr

6 White Gate Dr

Glen Head, NY
$249
Vacation Rentals, Unknown
Stately Brick Colonial on Majestic & Exquisite Three Acres In Old Brookville. Walking distance to all-organic Youngs Farm, in the middle of a private Homeowners Association Community Of 20 High End......

4 Wedgewood Ct

4 Wedgewood Ct

Glen Head, NY
$7,900
Vacation Rentals, Unknown
Welcome to this charming farm ranch on a private cul-de-sac. Nestled in the heart of the prestigious and highly sought-after neighborhood of Glen Head, this fully renovated abode is a true......

8 Black Rock Rd

8 Black Rock Rd

Glen Head, NY
$115
Vacation Rentals, Unknown
Spectacular architecturally exciting Sprawling cedar /stone contemporary with tremendous sense of elegance & style. Amazing open floor plan with natural light floor to ceiling windows overlook pool......

48 Smith St

48 Smith St

Glen Head, NY
$5,600
Vacation Rentals, Unknown
Experience the charm and elegance of this hi-ranch property, Located In The North Shore School District and within close proximity to the beach and LIRR Glen head station. Featuring 5 Beds 3 baths,......

33 Emerson Rd

33 Emerson Rd

Glen Head, NY
$15
Vacation Rentals, Unknown
Enjoy Living On One Of The Most Sought-Out Streets In All Of Brookville. On Over 2.6 Acres Lives This Exquisitely Totally Renovated Home With The Highest Quality Of Amenities. 5 Bedrooms, 5.5......

165749 Road

165749 Road

Glen Head, NY
$2,600
Vacation Rentals, Unknown
Newly renovated apartment with one master bedroom, big living room, bathroom, one kitchen, and one dining area. Freshly painted with new appliances and new floor. Easy walking to public transit......

Glenwood Rd

Glenwood Rd

Glen Head, NY
$1,900
Vacation Rentals, Unknown
COTTAGE FABULOUS COTTAGE 1 BEDROOM BRAND NEW ALL!! SPACIOUS FABULOUS LIVINGROOM WITH VAULTED CEILING WITH BEAUTIFUL SKYLIGHTS THAT LIGHT UP THE ENTIRE ROOM, WATCH THE STARS !! ALLL NEW WOOD FLOORS.......

0 Hegemans Ln

0 Hegemans Ln

Glen Head, NY
$3,500
Vacation Rentals, Unknown
2 Bedroom Cottage Just Renovated With Private Deck. Very Large Bedrooms With Plenty Of Closets. Utilities Are Included 1 Month Security Broker Fee Is 10% Of 1st Years Rent, Renters Insurance......

Copperfield Ln

Copperfield Ln

Glen Head, NY
$2,300
Vacation Rentals, Unknown
This 1 bedroom apartment features high ceilings , living room/ dining, kitchen and 1 bathroom. House is located in a private residential area with ample parking. The house is located close to the......

Copperfield Ln

Copperfield Ln

Glen Head, NY
$3,550
Vacation Rentals, Unknown
Glen Head/Old Brookville: 1 bedroom, 1 bath cottage home. Outdoor area....

106 Wolver Hollow Rd

106 Wolver Hollow Rd

Glen Head, NY
$4,200
Vacation Rentals, Unknown
Freestanding cottage. Excellent condition. New appliances. Patio and Grassy Yard. Upper Brookville location. Very private....

157 Linden Ln

157 Linden Ln

Glen Head, NY
$15
Vacation Rentals, Unknown
Gold Coast living fit for today's modern lifestyle! Step into this chic, sophisticated most magnificent 2+ acre estate in Upper Brookville with a newly renovated interior to match. Grand Entry......

174 Hegemans Ln

174 Hegemans Ln

Glen Head, NY
$4,300
Vacation Rentals, Unknown
Newly Renovated Cottage Located In The North Shore School District. It Features 3 Bedrooms, 2.5 Bath, Large Kitchen, Living Room, Formal Dinning Room, Den, Laundry Room, Partial unfinished......

Chicken Valley Rd

Chicken Valley Rd

Glen Head, NY
$3,500
Vacation Rentals, Unknown
Single level living! Spacious 3 bedroom/ 3 bathroom. Living room with beautiful vaulted ceilings. Large deck overlooking multiple acres bordering country club. Centrally located, prime Upper......

Locust Ave

Locust Ave

Glen Head, NY
$4,200
Vacation Rentals, Unknown
Picture Perfect 3 Bedroom 2 Full Bath 2023 Renovated Brick Cape Cod Centrally Located Near Glen Head Train Station For Easy Access To New York City. Beautiful New Kitchen w/Stainless Steel......

Glen Head, NY

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