Shelter Island Heights Holiday Homes from €224: Search Top House Rentals

Shelter Island Heights Holiday Homes
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A pebbled beach with a sunset and a distant bridge.

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Our top choices for Shelter Island Heights holiday homes

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

A sign welcoming visitors to the Greenport Visitors Dock with no commercial traffic.

A compact kitchen with white cabinets, a built-in oven, a microwave, and a washing machine.

A two-story house with a balcony, a patio with outdoor furniture, and a fenced backyard.

1. The SandPiper

The SandPiper

Pipes Cove

9.6 out of 10, Exceptional, (52 reviews)

9.6/10

Exceptional

(52 reviews)

"Very wonderful location so close to the train station will come back soon"

Julian V.

The price is €224

€224

includes taxes & fees

2 Nov - 3 Nov

The SandPiper

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

A marina with several fishing boats docked.

A modern kitchen with a washing machine, microwave, oven, and a ceiling fan.

A wicker lounge chair with a white cushion on a covered deck, surrounded by a white fence.

2. Aqua Vista

Aqua Vista

Pipes Cove

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Great location and nice spot."

Kerri L.

The price is €226

€226

includes taxes & fees

1 Nov - 2 Nov

Aqua Vista

A beach with people relaxing, a pier extending into the water, and a clear sky.

A two-story house with a front porch and a pathway leading to the entrance.

A dock with a sign reading 'Welcome to the Greenport Visitors Dock' and 'No Commercial Traffic.'

A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"We had a great stay!! "

Callie E.

The price is €342

€342

includes taxes & fees

1 Nov - 2 Nov

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

An outdoor dining area with hanging lights, palm trees, and a bar.

A modern bedroom with a four-poster bed, a television, a heater, and a brick wall.

A building with a porch, a tree, and a sign that reads "OPEN SPACE".

A staircase with steps labeled 'STAIRWAY TO HEAVEN' leading to a room with a lamp and a plant.

4. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport

9.4 out of 10, Exceptional, (6 reviews)

9.4/10

Exceptional

(6 reviews)

"Great place! So nice."

Paul F.

The price is €276

€276

includes taxes & fees

8 Oct - 9 Oct

American Beech in Greenport - Petite King Room 7

A wooden pathway leading to a beach with scattered rocks and greenery.

A spacious living room with a gray sofa, a wooden coffee table, and a dining area with a wooden table and chairs.

A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

A cozy room with a gray sofa, wooden walls, and large windows with blinds.

5. Beach Block Hideaway

Beach Block Hideaway

Pipes Cove

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."

Teresa C.

The price is €448

€448

includes taxes & fees

4 Oct - 5 Oct

Beach Block Hideaway

A modern dining area with a wooden table, white chairs, and a chandelier.

A living room with a grey sofa, a round coffee table with magazines, a wooden side table, and a large mirror on the wall.

A bedroom with a bed, a small side table with a plant, and a window with blinds.

A staircase with a black handrail and balusters, a white wall, a fireplace with a TV above it, and a door to the right.

6. Northfork Townhouse walk to all

Northfork Townhouse walk to all

Greenport

9.4 out of 10, Exceptional, (8 reviews)

9.4/10

Exceptional

(8 reviews)

"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"

Beth R.

The price is €775

€775

includes taxes & fees

8 Oct - 9 Oct

Northfork Townhouse walk to all

A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

A dining area with a wooden table, white chairs, and a vase of sunflowers.

A modern kitchen with white cabinetry, stainless steel appliances, and a herringbone-patterned backsplash.

A bedroom with a bed, a bench, a chandelier, and a wall-mounted mirror.

7. Renovated Townhouse walk to all

Renovated Townhouse walk to all

Greenport

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"The place was as advertised and in great walking distance to everything in town! "

Liz H.

The price is €674

€674

includes taxes & fees

8 Oct - 9 Oct

Renovated Townhouse walk to all

An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

A hotel reception desk with a white counter, a wooden reception desk, and a green exit sign.

A four-poster bed with a bench, bedside tables, a flat-screen TV, and a window with blinds.

A greenhouse with a checkered floor, a table with a lamp, and a potted plant.

8. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6

Greenport

2.0 out of 10, (1 review)

2.0/10

(1 review)

"Not as advertised. Very disappointed "

Jeffrey

American Beech in Greenport - Deluxe King 6

A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

A coastal property with a large house, a smaller building, and a landscaped garden.

A sunlit room with large windows overlooking a beach, featuring a wooden table and chairs, and a small round table with a chair.

A bedroom with a large bed, a ceiling fan, and a view of the ocean through large windows.

9. Beachfront Greenport Villa

Beachfront Greenport Villa

Greenport

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Beautiful home, great views and host!"

Kate R.

The price is €1,123

€1,123

includes taxes & fees

2 Nov - 3 Nov

Beachfront Greenport Villa

A dining area with a round table, six chairs, and a chandelier.

A bedroom with a large bed, two bedside tables, a nightstand, and a window with curtains.

A well-maintained lawn with a variety of trees and a small building, likely a house, surrounded by a fence.

A modern living room with a black sofa, a grey armchair, and a black coffee table.

10. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home

East Hampton

9.2 out of 10, Wonderful, (7 reviews)

9.2/10

Wonderful

(7 reviews)

"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "

Suzanne R.

The price is €1,189

€1,189

includes taxes & fees

4 Oct - 5 Oct

Year round Jacuzzi - Blackberry Home

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

A garden with hydrangea bushes, a stone wall, and a covered area with plants.

A living room with a green sofa, a small round table with a board game, a blue vase with dried plants, and a white arched cabinet.

A wicker outdoor seating area with a dog on a cushioned bench.

11. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"

maria m.

The price is €987

€987

includes taxes & fees

3 Oct - 4 Oct

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

A stone pier leading to a beach with houses in the background.

A two-story building with a balcony and large windows, likely a restaurant or cafe.

A cozy interior with a dining area, a seating area with a patterned rug, and a kitchen with a microwave and refrigerator.

A dining area with a wooden table and white chairs, a teal bookshelf with decorative items, and a window with blinds.

12. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme

9.4 out of 10, Exceptional, (61 reviews)

9.4/10

Exceptional

(61 reviews)

"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."

Emily M.

The price is €240

€240

includes taxes & fees

14 Oct - 15 Oct

Insta-worthy Couples Retreat: Perfect for romantic getaway!

A rectangular swimming pool with a pebble border and a fire feature in the center.

A wooden porch with a blue door, a bench, and a table.

A two-story house with a front porch, a brick chimney, and a well-maintained garden.

A hallway with a bench, a fireplace, and a view of the living room.

13. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

East Hampton North

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

The price is €836

€836

includes taxes & fees

8 Oct - 9 Oct

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

A driveway with a parked car, surrounded by trees and illuminated pathway lights.

A modern room with a bed, sofa, and a small table. There is a painting on the wall, a TV, and a lamp.

A modern living room with a grey sofa, a round coffee table, and a painting of a pelican.

A beach with sand dunes and a wooden bench.

14. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."

Robert R.

The price is €534

€534

includes taxes & fees

1 Nov - 2 Nov

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

A dining area with a wooden table and white chairs, a vase with flowers, and a painting on the wall.

A little outdoor space to relax and enjoy the fresh air.

A living room with a black sofa, blue armchairs, a coffee table, and a flat-screen TV.

15. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

East Lyme

9.0 out of 10, Wonderful, (7 reviews)

9.0/10

Wonderful

(7 reviews)

"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."

Sarah G.

The Bay Cottage · Rocky Neck Park, Beach & Niantic

A modern building with large windows overlooking a beach.

A modern bedroom with a large bed, a wardrobe, a mirror, and a view of the sea.

A modern kitchen with a view of the sea, large windows, and a sliding glass door to the outdoors.

A spacious living area with a modern staircase, a dining area, and a kitchen.

16. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

9.4 out of 10, Exceptional, (20 reviews)

9.4/10

Exceptional

(20 reviews)

"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."

Donald J.

The price is €1,090

€1,090

includes taxes & fees

4 Oct - 5 Oct

Beachfront Jacuzzi All Year - Black Swan Home

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

A modern living room with two armchairs, a sofa, a coffee table, and a large window with curtains.

A covered outdoor seating area with a wicker sofa and a coffee table, surrounded by greenery.

A kitchen with white cabinetry, a dining table with chairs, a hanging light fixture, and a door with a frosted glass panel.

17. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 reviews)

"Very clean & comfortable home, great host & location! "

Becky W.

The price is €406

€406

includes taxes & fees

4 Oct - 5 Oct

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

A living room with a wooden dining table, two grey upholstered chairs, a grey sofa, and a white coffee table.

A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

A narrow hallway leading to a bedroom with a sloped ceiling and a bed with patterned bedding.

18. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town

Westbrook Center

9.2 out of 10, Wonderful, (17 reviews)

9.2/10

Wonderful

(17 reviews)

"Very nice small place to stay by the beach and close to great coffee shop. "

Donovan V.

The price is €450

€450

includes taxes & fees

15 Oct - 16 Oct

Adorable Cottage, 5 min walk to water & town

A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

A porch with a blue door, white columns, and a stone floor.

A room with a white bench, a small table with a lamp, and a window with a view of greenery.

A stone-paved entrance with steps leading to a white door, surrounded by potted plants and a small garden.

19. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Saybrook Manor

9.8 out of 10, Exceptional, (140 reviews)

9.8/10

Exceptional

(140 reviews)

"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."

Alexis L.

The price is €491

€491

includes taxes & fees

12 Oct - 13 Oct

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

A house with a swimming pool, surrounded by trees and a fenced yard.

A modern living room with a sofa, armchair, and coffee table, a large mirror, and a TV.

A modern kitchen with a central island, stainless steel appliances, and a skylight.

20. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

9.6 out of 10, Exceptional, (27 reviews)

9.6/10

Exceptional

(27 reviews)

"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"

Annie B.

The price is €1,492

€1,492

includes taxes & fees

4 Oct - 5 Oct

Jacuzzi year-round - Villa Luz Private Home

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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