This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Shelter Island Vacation Rentals Show this location only Back to top
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Relax by the Pool at This Comfortable 3 Bedroom Retreat
3BR+/2BA
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Sleeps 6
– Shelter Island #245424
$400 - $535 per night 6-7 night min stay
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Perfect House for a Large Family & Those Who Love to Entertain
3BR+/3.5BA
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Sleeps 6-8
– Shelter Island #304851
$500 per night 5 night min stay
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Beautiful, Waterfront Home with Dock and Heated Saltwater Gunite Pool!
5BR/3BA
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Sleeps 10
– Shelter Island #425548
From 4500 to 7500 per week
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The Perfect Summer Rental in the Hamptons! Seasonal or Monthly Only!
7BR/6.5BA
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Sleeps 16
– Shelter Island #459326
see recap
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Shelter Island Waterfront Cottage-Coecles Harbor, Family/Pet Friendly.
1BR+/1BA
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Sleeps 7-8
– Shelter Island #420558
Weekly from $1300 - $2500 per week.
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Gorgeous Home in Beach Community with Heated Saltwater Pool
4BR/3BA
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Sleeps 10
– Shelter Island #115762ha
$5600 - $5950 per week 7-31 night min stay
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Chic + Modern Farmhouse on 2 Acres Shelter Island, Hamptons
4BR/3BA
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Sleeps 8
– Shelter Island #343949
From $3500/ week
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Beautiful Shelter Island Summer Home Rental
3BR+/3BA
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Sleeps 8-10
– Shelter Island #305998
$2400/wk, immed. off season, $1800/wk.
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A Perfect Little Gem of a House on a Perfect Little Island
2BR/1BA
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Sleeps 4
– Shelter Island #239698
$150-$250/nt or $950-$1700/wk
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Charming Waterview Cottage - Shelter Island, Hamptons
4BR/2BA
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Sleeps 7-8
– Shelter Island #98506
$2,500-$4,000/wk - $8,500-$15,000/mo
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Comfortable Waterfront Home with Pool and Dock
4BR+/3BA
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Sleeps 10-12
– Shelter Island #313937
From $4,000/wk to $18,000/mo
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Shelter Island Farmhouse with Pool
3BR+/1.5BA
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Sleeps 6-8
– Shelter Island #292262
$400/500/wk
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Beautiful Shelter Island Home on Chase Creek
4BR+/3.5BA
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Sleeps 8
– Shelter Island #137734
$5,000/wk - $20,000/mo
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Charming, Renovated Island Cottage
2BR+/1BA
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Sleeps 4-6
– Shelter Island #360888
From $175/nt - $325/nt
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Shelter Island Cottage - Beautiful Waterfront Location
2BR+/2BA
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Sleeps 4-6
– Shelter Island #164986
$1800- $2500/wk
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Cozy Cottage Steps to Water- Shelter Island
2BR+/2BA
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Sleeps 4-8
– Shelter Island #221060
$4000- $8000/mo
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Sunny Shelter Island Home, Walk to Private Beach
3BR+/2BA
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Sleeps 7
– Shelter Island #338964
$1,500 - $3,000 weekly
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Design and Comfort Come Together in This Island Beach Home
3BR/3BA
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Sleeps 7
– Shelter Island #944956ha
$1 - $675 per night 3-14 night min stay
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Art Loving Sailors' Zen Retreat--Waterfront 5 Bedroom House
5BR+/4BA
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Sleeps 10-12
– Shelter Island #344072
From $1,500 - $6,500/wk US Dollar or Euros
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Waterfront Shelter Island House with Dock on Ram Island
4BR/3BA
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Sleeps 8-10
– Shelter Island #221097
High season $5500/wk
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Luxury,Quiet, Pool,Spotless, Beach,Main+Guest House,June Still Avail!
6BR+/7BA
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Sleeps 12-14
– Shelter Island #3505246ha
$714 - $1056 per night
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Contemporary Home with Old Vocabulary in Walking Distance to Beaches
4BR/3BA
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Sleeps 8
– Shelter Island #3531549ha
$200 - $367 per night
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Eclectic Round House- 4 Bedroom+Cottage+Pool on 1.5 Priv Acres
4BR/3.5BA
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Sleeps 10
– Shelter Island #390379
From 1500/wk
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Charming Country 4 BR/4 BA Retreat Available July & August
4BR/4BA
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Sleeps 6-8
– Shelter Island #293917
$3500/wk
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Relax in This Spacious, Light-Filled Vacation Home in Coveted Silver Beach
3BR/2BA
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Sleeps 6
– Shelter Island #3554393ha
$286 - $357 per night 1-7 night min stay
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Private Beautiful Home 2 Acres with Large Pool, Walk to Wades Beach
4BR/3BA
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Sleeps 10
– Shelter Island #472283
$500 - $928 per night 14 night min stay
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Great Poolside Home
4BR+/2BA
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Sleeps 9-12
– Shelter Island #299978
$2000- $4250/wk
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Gardiners Creek with a Dock and Cottage
5BR+/5BA
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Sleeps 10-12
– Shelter Island #386414
$4,000- 6,000 wk
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Spacious Shelter Island Escape - Walking Distance to Beach
4BR+/2BA
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Sleeps 8-10
– Shelter Island #368096
2150 (June 2013)
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Stylish Shelter Island Home with Pool and Walk to Beach.
3BR/2.5BA
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Sleeps 6
– Shelter Island #356336
$2,500- $4,350/wk - $12,000-$18,000/mo
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Classic Modern Cottage
3BR+/2BA
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Sleeps 6-7
– Shelter Island #419654
$233 per night 6 night min stay
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Waterfront Home with Beach & Deep-Water Dock
4BR+/4BA
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Sleeps 10
– Shelter Island #82578
$2750/wk
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Shelter Island, NY Fully Renovated Farmhouse with Heated Pool
3BR+/2BA
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Sleeps 6-8
– Shelter Island #361132
From $1500/wknd
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Beach Cottage - 2013 Season: Walking Distance to Wades Beach
3BR+/2BA
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Sleeps 6-8
– Shelter Island #286069
$2450 per week 7 night min stay
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Spend the Summer in Bucolic Shelter Island
3BR/2BA
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Sleeps 4-6
– Shelter Island #118075
$7,500- $18,500/mo
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Waterfront Home W/ Gunite Pool /Dock Plus Guest Studio
4BR/2BA
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Sleeps 5-7
– Shelter Island #412629
August -LD 27,000.-
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Romantic Cottage Retreat Walk to Beach Golf Deli & Ferry
1BR/2BA
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Sleeps 2
– Shelter Island #425263
$4500 - $6000 per month 29-30 night min stay
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Beautiful Beach Cottage
3BR/2BA
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Sleeps 6
– Shelter Island #459546
$4193 per week 7 night min stay
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Peaceful-Secluded-Simple. 3BR Farmhouse W/ Sep. Studio Cottage
3BR+/2.5BA
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Sleeps 6-10
– Shelter Island #397752
$1694 - $1995 per week 7-31 night min stay
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Tennis Court, Pool, Luxury Shelter Island 3-Bedroom
3BR/2.5BA
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Sleeps 8
– Shelter Island #90560
$5000- $7000/wk
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Beautiful, Secluded, Waterfront with Wrap-Around Porch and Roof Deck
4BR/3BA
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Sleeps 7-9
– Shelter Island #452492
$1000 per night 3 night min stay
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Contemporary and Private in Beach Community
3BR/3BA
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Sleeps 6
– Shelter Island #426436
$2940 - $3920 per week 7 night min stay
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Cottage by the Bay
2BR+/2BA
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Sleeps 4-6
– Shelter Island #426604
Note: Until confirmed, rates are subject dollar
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Beautiful Secluded Family Home Across from Dering Harbor.
4BR+/3BA
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Sleeps 6-10
– Shelter Island #411447
$18,000.00/month
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Shelter Island Waterfront Beach House - Private Beach Perfect Sunsets
3BR/2BA
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Sleeps 8
– Shelter Island #470387
$465 per night 14 night min stay
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Tranquil Waterfront Gingerbread Cottage-Don't Miss This One!!!
2BR/2.5BA
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Sleeps 4-6
– Shelter Island #471275
From $1250. per week
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Quaint, Charming House Close to Everything
2BR+/1BA
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Sleeps 4-6
– Shelter Island #412420
From $150/n
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Charming and Private, Secluded Garden Setting with Pool
3BR/2BA
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Sleeps 6-8
– Shelter Island #450883
$3000 per week 7 night min stay
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Contemporary Cottage!
3BR/2BA
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Sleeps 6-7
– Shelter Island #248925
From $1,000/wk - $11,000/mo
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Shelter Island Jewel
4BR/4BA
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Sleeps 8
– Shelter Island #473627
$5075 - $5950 per week 7-31 night min stay
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Gorgeous Renovated Barn with Pool
4BR/2BA
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Sleeps 8
– Shelter Island #284150
$5000- $8500/wk
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Boater's Delight
5BR/2BA
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Sleeps 8-9
– Shelter Island #461734
$10,000 - $14,000/month US
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Family Friendly Home in Idyllic Setting Close to Beach
3BR/2BA
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Sleeps 6-8
– Shelter Island #470139
$195 - $449 per night 14 night min stay
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Stylishly Renovated Cottage on 1.5 Acres with Pool
3BR/2BA
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Sleeps 5
– Shelter Island #474895
$3640 - $5040 per week 7-31 night min stay
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Peace and Quiet on Shelter Island
6BR/3.5+BA
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Sleeps 12
– Shelter Island #411046
From $3000/week
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Sweet Cottage, Close But Not Too Close to All that You Need
1BR/1BA
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Sleeps 2-4
– Shelter Island #368838
$150/Night... $1,000/Week
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Fabulous Easy Living Waterfront with Dock
4BR/3BA
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Sleeps 8-10
– Shelter Island #422449
4000- 7000 week USD/GBP/EUR
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Location! Historic District Recently Renovated,a/C, Waterview
4BR+/3.5BA
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Sleeps 9
– Shelter Island #342282
3000 wk
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Upscale New Home, Heated Pool, First & Second Floor Suites.
5BR/3.75BA
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Sleeps 10
– Shelter Island #355233
$4,000 to $7,000/wk
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Beach House, Water View, Saline /Heated Pool, 100ft to Beach
4BR+/2BA
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Sleeps 7-9
– Shelter Island #380593
FROM $1,500/MONTH TO $5,000/WEEK
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Winner of Best of Citysearch- Beach/Pool, 4+ Bedroom Hamptons Vacation
5BR/4BA
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Sleeps 10
– Shelter Island #184172ha
$250 - $985 per night
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Tranquil Island Refuge Nestled Among Towering Trees and Near Private Beach
3BR/2BA
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Sleeps 6
– Shelter Island #248802ha
$271 - $368 per night
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Rustic House W/ Pool on 2 Private Acres
3BR/2BA
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Sleeps 6
– Shelter Island #250830ha
$267 - $500 per night
- Adorable Waterfront Cottage 2BR/1BA – Sleeps 6 – Shelter Island #391665ha
- Spectacular Architects Waterfront Greek Revival 5BR/4BA – Sleeps 9 – Shelter Island #227764ha
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Charming, Historic Cottage
3BR/2BA
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Sleeps 6
– Shelter Island #3525659ha
$250 - $500 per night 2-7 night min stay
- Sun Worshipers Paradise 3BR/1.5BA – Sleeps 6 – Shelter Island #238094ha
- Waterfront Charmer on Idyllic Shelter Island for Summer Rental 3BR/3BA – Sleeps 8 – Shelter Island #364166ha
- Peace and Quiet on Shelter Island 4BR+/2.5BA – Sleeps 8 – Shelter Island #189852ha
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Charming Cottage. June Available. Can Rent Year Around.
3BR/1BA
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Sleeps 3
– Shelter Island #999295ha
$5003 - $5075 per month 29 night min stay
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Shelter Island Renovated Barn Hideaway Pool • Water Access • Hamptons
2BR+/1BA
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Sleeps 6
– Shelter Island #998344ha
$11030 - $19375 per month 14-31 night min stay
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Nature Lover's Delight!
3BR/2.5BA
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Sleeps 6
– Shelter Island #3558053ha
$3500 - $5425 per week 7 night min stay
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Very Elegant, with Hot Tub, Large Deck and Lush Landscape
3BR/3BA
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Sleeps 8
– Shelter Island #385658ha
$233 - $500 per night
- September on Shelter Island is the Perfect Place at the Perfect Time! 1BR+/1BA – Sleeps 3 – Shelter Island #299991ha
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Two Acre Waterfront Estate with Renovated Historic Home, Shelter Island NY
4BR/3BA
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Sleeps 7
– Shelter Island #376553ha
$107 - $1429 per night
- Coecles Harbor Ram Island Waterfront Estate 3BR/2BA – Sleeps 6 – Shelter Island #3007870ha
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Breathtaking & Charming Shelter Island Oasis 5BR 3.5BA on Private Acre
5BR/3.5BA
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Sleeps 6-10
– Shelter Island #3022336ha
$500 - $1000 per night
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Romantic Hamptons Beach Cottage! Seclusion, Waterfalls
2BR+/1.5BA
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Sleeps 6
– Shelter Island #3513499ha
$233 - $554 per night
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Romantic Waterfront Hideaway
4BR/7BA
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Sleeps 10-14
– Shelter Island #3539427ha
$786 - $833 per night
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Relax by the Pool at This Comfortable 3 Bedroom Retreat
3BR+/2BA
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Sleeps 6
– Shelter Island #245424
Overview of Shelter Island Vacation Rentals
You Will Love Shelter Island Vacation Rentals
Shelter Island vacation rentals are so great, you will recommend them to friends for years after your visit to the area! From adorable shack-like cafes to charming mom n' pop restaurants, you will find unique establishments in Shelter Island that are unlike anything you have experienced before! Enjoy a day strolling along the waterfront, observing the native wildlife, or visit the Mashomack Preserve to see 2,100 acres of Nature Conservancy. Either way, you will be touched by the efforts of the locals to preserve the natural elegance and charm of their neighborhood.
Summer Homes in Shelter Island Couldn't Be More Lovely
Summer homes in Shelter Island are so lovely, they could not be improved upon. Enjoy great beaches like Sailors' Haven, for days of sunbathing and picnicking on the sand, or spend your days indoors. The great thing about Shelter Island summer homes is that you can relax, enjoy the privacy, and spend time working on your novel or catching up on letter writing. Take a day trip to Long Island for hip clubs, five star restaurants, and high-end shopping, or stroll through The Hamptons star watching for frequent visitors like Gwyneth Paltrow and Jerry Seinfeld.
House Rentals in The Hamptons Are Something You'll Never Forget
House rentals in The Hamptons are not just a place to live for a few weeks each summer, they're an experience that you will remember forever. Rub elbows with celebrities like Paul McCartney, or get away from the crowds and visit Dead Man's Hill on Corona Avenue. Go clamming on the beach, or pick raspberries inland. There are quaint activities to be done in Shelter Island, and all over The Hamptons, that will make you feel relaxed and happy. You will love your trip to The Hamptons, and always remember it as the place where you had the best peaches in the world!