Shelter Island Vacation Rentals
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Vacation Rentals in Shelter Island
Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1022)
The price is ¥26,374
¥33,168 total
includes taxes & fees
May 29 - May 30
Windward Shores Ocean Resort
Windward Shores Ocean Resort
8.8 out of 10, Excellent, (236)
The price is ¥32,751
¥40,787 total
includes taxes & fees
May 29 - May 30
The Surf Club
The Surf Club
8.4 out of 10, Very Good, (220)
The price is ¥35,145
¥48,637 total
includes taxes & fees
Jun 13 - Jun 14
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Montauk Oceanside Suites
Montauk Oceanside Suites
8.4 out of 10, Very Good, (299)
The price is ¥26,545
¥31,864 total
includes taxes & fees
Jun 12 - Jun 13
Driftwood Resort
Driftwood Resort
8.8 out of 10, Excellent, (187)
The price is ¥25,203
¥32,172 total
includes taxes & fees
May 29 - May 30
Cliffside Resort Condominiums
Cliffside Resort Condominiums
9.0 out of 10, Wonderful, (181)
The price is ¥42,819
¥55,685 total
includes taxes & fees
Jun 23 - Jun 24
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
North Fork Escape Near Wineries, Beaches And Hamptons
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
Newly Renovated Montauk Condo with Ocean Views!
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (62)
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (72)
Beautiful Family Home Nestled In The Heart Of Sagaponack
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (25)
MONTAUK MANOR-DELUXE STUDIO APARTMENT
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
Location and views! Located directly on Shinnecock Bay!
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (28)
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (73)
Beach House
Beach House
9.8 out of 10, Exceptional, (43)
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
The price is ¥51,022
¥93,414 total
includes taxes & fees
Jun 13 - Jun 14
Gorgeous private Hamptons house with pool and volleyball court
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, (7)
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (91)
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.
Other types of properties in Shelter Island you may be interested in
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
7.6 out of 10, Good, (964)
The price is ¥15,872
¥18,253 total
includes taxes & fees
Jun 5 - Jun 6
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
8.2 out of 10, Very Good, (570)
The price is ¥88,267
¥120,337 total
includes taxes & fees
Jun 2 - Jun 3
The Bentley Hotel Southampton
The Bentley Hotel Southampton
9.4 out of 10, Exceptional, (74)
The price is ¥30,932
¥42,269 total
includes taxes & fees
Jun 3 - Jun 4
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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Frequently asked questions
Recent reviews of Shelter Island propertiesExpedia verified reviews
5/5 Excellent
"Just what you need for a quick stay. Really great breakfast option across the street. Hard to get anything late. "
A verified traveler from BROOKLYN stayed at Pier Blue Inn Old Saybrook - Essex
Posted 11 hours ago