Shelter Island Heights Rentals

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332 Houses

24

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island / Shelter Island Heights

Shelter Island Heights cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$441

Responds fast!
avg. 8 minutes

Price per night from

$441

49

55 Shore

Shelter Island / Shelter Island Heights

Shelter Island Heights villa

6 12 15 nights min

  • 6 bedrooms
  • sleeps 12
  • 15 nights min
  • Ask about children
  • Ask about pets

Price per night from

$4,000

Responds fast!
avg. 1 hour 15 minutes

Price per night from

$4,000

Great rentals within 20 miles that match your search

Distance approx 1.88 km from Shelter Island Heights

13

Remodeled Greenport Farmhouse

North Fork / Greenport

Greenport farmhouse

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$426

Price per night from

$426

Distance approx 2.86 km from Shelter Island Heights

(5) Excellent 

23

Beautiful French Country Cottage

North Fork / East Marion

East Marion cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$401

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$401

Distance approx 14.9 km from Shelter Island Heights

24

NEW! Quiet Clinton House Steps to Private Beaches!

Connecticut / Clinton

Clinton house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 10 minutes

Price per night from

$175

Distance approx 2.06 km from Shelter Island Heights

(11) Excellent 

Certificate of Excellence

14

Waterfront Condo C204 at The Cliffside Resort

North Fork / Greenport

Greenport apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Certificate of Excellence

Price per night from

$251

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$251

Distance approx 16.93 km from Shelter Island Heights

19

THE PERFECT HAMPTON'S BEACH HOUSE 200 FT TO OCEAN

Hamptons / Amagansett

Amagansett house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$788

Price per night from

$788

Distance approx 15.66 km from Shelter Island Heights

13

Walk to the beach

Southampton / Hampton Bays

Hampton Bays house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$701

Responds fast!
avg. 1 hour 12 minutes

Price per night from

$701

Distance approx 8.47 km from Shelter Island Heights

(1) Excellent 

16

East Hampton/ Sag Harbor, 8 Acres, Pool, Tennis Ct, Hot tub, Sauna

Hamptons / East Hampton

East Hampton house

5 8 7 nights min

  • 5 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 7 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,187

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$1,187

Distance approx 6.64 km from Shelter Island Heights

(1) Excellent 

14

North Fork Beach House on LI Sound

North Fork / Peconic

Peconic cottage

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$430

Price per night from

$430

Distance approx 10.82 km from Shelter Island Heights

18

Waterview renovated 5 bedroom house with pool

Hamptons / East Hampton

East Hampton house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,001

Price per night from

$1,001

Distance approx 10.3 km from Shelter Island Heights

7

Spectacular 5 Bedroom Contemporary Getaway..Private Oasis........Newly Renovated

Hamptons / East Hampton

East Hampton house

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,601

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$1,601

Distance approx 15.19 km from Shelter Island Heights

(2) Excellent 

32

Immaculate 4BR Southampton House w/Private Pool!

Hamptons / Southampton

Southampton house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$701

Responds fast!
avg. 10 minutes

Price per night from

$701

Distance approx 10.38 km from Shelter Island Heights

27

Comfort and quality w Pool,Tennis, Home Theater, Sonos Music System

Hamptons / East Hampton

East Hampton house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$451

Responds fast!
avg. 3 hours 25 minutes

Price per night from

$451

Distance approx 10.79 km from Shelter Island Heights

86

East Hampton 7 bedroom, 6 bath, heated pool, theater, contemporary smart home!

Hamptons / East Hampton

East Hampton house

7 22 3 nights min

  • 7 bedrooms
  • sleeps 22
  • 3 nights min
  • Child Friendly

Price per night from

$2,056

Responds fast!
avg. 54 minutes

Price per night from

$2,056

Distance approx 10.98 km from Shelter Island Heights

11

Peacful Cottage In One Of Southampton's

Hamptons / Southampton

Southampton cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$401

Price per night from

$401

Distance approx 14.63 km from Shelter Island Heights

6

Seahaven Resort Motel Unit 10

Hamptons / Southampton

Southampton hotel apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 11.86 km from Shelter Island Heights

25

piece of Heaven

North Fork / Mattituck

Mattituck house

4 14 30 nights min

  • 4 bedrooms
  • sleeps 14
  • 30 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$1,501

Price per night from

$1,501

Distance approx 14.63 km from Shelter Island Heights

9

Seahaven Resort Motel Unit 8

Hamptons / Southampton

Southampton hotel apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 2.89 km from Shelter Island Heights

(5) Excellent 

39

Five Bedroom Italianate Great House - The Gem of East Marion

North Fork / East Marion

East Marion house

5 9 1 night min

  • 5 bedrooms
  • sleeps 9
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$952

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$952

Distance approx 2.64 km from Shelter Island Heights

19

Waterfront Charmer on idyllic Shelter Island

Hamptons / Shelter Island

Shelter Island house

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$931

Price per night from

$931

Distance approx 10.79 km from Shelter Island Heights

24

NEW-Rustic East Hampton Family Home Mins to Beach!

Hamptons / Springs

Springs house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$226

Responds fast!
avg. 10 minutes

Price per night from

$226

Distance approx 15.73 km from Shelter Island Heights

11

Guest Cottage

Southampton / Hampton Bays

Hampton Bays apartment

1 4 13 nights min

  • 1 bedroom
  • sleeps 4
  • 13 nights min
  • Air conditioning
  • Private garden

Price per night from

$201

Price per night from

$201

Distance approx 13.89 km from Shelter Island Heights

17

Southampton Village Charmer with New Heated Pool

Hamptons / Southampton

Southampton house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,501

Price per night from

$1,501

Distance approx 12.86 km from Shelter Island Heights

15

Walk to Beach, Contemporary, Amagansett, Eash Hamp

Hamptons / East Hampton

East Hampton house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

Price per night from

$644

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$644

Distance approx 14.63 km from Shelter Island Heights

9

Seahaven Resort Motel Unit 12

Hamptons / Southampton

Southampton hotel apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$210

Price per night from

$210

Distance approx 2.15 km from Shelter Island Heights

13

"This must be the place"

North Fork / Greenport

Greenport house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$529

Price per night from

$529

Distance approx 9.99 km from Shelter Island Heights

17

Cottage european charm private beach in Southampton, North Sea

Hamptons / Southampton

Southampton house

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Child Friendly

Price per night from

$472

Price per night from

$472

Distance approx 10.74 km from Shelter Island Heights

26

Elegant East Hampton Home - Pool & Putting Green

Hamptons / East Hampton

East Hampton house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$539

Responds fast!
avg. 14 minutes

Price per night from

$539

Distance approx 7.92 km from Shelter Island Heights

17

Forest Guest Suite

Hamptons / Sag Harbor

Sag Harbor house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 4 mi
  • Air conditioning
  • Private garden

Price per night from

$176

Price per night from

$176

Distance approx 16.44 km from Shelter Island Heights

(8) Excellent 

6

Beach Bungalow with Private Beach

Hamptons / Amagansett

Amagansett house

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$601

Price per night from

$601

Distance approx 12.27 km from Shelter Island Heights

14

Charmimg Beach cottage in Sagaponack

Hamptons / Southampton

Southampton house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$573

Price per night from

$573

Distance approx 14.63 km from Shelter Island Heights

7

Seahaven Resort Motel Unit 17

Hamptons / Southampton

Southampton hotel apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

Distance approx 13.86 km from Shelter Island Heights

24

Bishops Pond Southampton NY

Hamptons / Southampton

Southampton townhouse

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$183

Price per night from

$183

Distance approx 16.91 km from Shelter Island Heights

(10) Excellent 

37

North Fork 5 bed room home with forever farm view

Riverhead / Aquebogue

Aquebogue house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$401

Price per night from

$401

Distance approx 7.73 km from Shelter Island Heights

14

North Fork Long Island Wine Country Cottage, Water Views

North Fork / Cutchogue

Cutchogue house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$276

Price per night from

$276

Distance approx 4.78 km from Shelter Island Heights

24

Beach Front, spacious 5 Bedrooms, North Fork, Long Island

North Fork / Southold

Southold house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$526

Price per night from

$526

Distance approx 10.87 km from Shelter Island Heights

(4) Excellent 

17

Bridgehampton South, Village Gem. Location, Location, Location!

Hamptons / Bridgehampton

Bridgehampton house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$796

Price per night from

$796