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Shelter Island Holiday Rentals

Hotels (4)

B&Bs / Inns (3)

Speciality Lodging (0)

Holiday Rentals (44)

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O3C28, Old Lyme
O3C28
    Price: £970 - £1,232/week
  • Bedrooms: 3, sleeps 5
  • Bathrooms: 1
    • Contact Manager
O1W29, Old Lyme
O1W29
    Price: £1,005/week
  • Bedrooms: 3, sleeps 7
  • Bathrooms: 2
    • Contact Manager
O2C56, Old Lyme
O2C56
    Price: £495 - £686/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O4S46U, Old Lyme
O4S46U
    Price: £543 - £741/week
  • Bedrooms: 4, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O1W62, Old Lyme
O1W62
    Price: £1,111 - £1,759/week
  • Bedrooms: 4, sleeps 7
  • Bathrooms: 2
    • Contact Manager
O2W67, Old Lyme
O2W67
    Price: £730 - £1,012/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O3F4, Old Lyme
O3F4
    Price: £566 - £747/week
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 1
    • Contact Manager
O2A91, Old Lyme
O2A91
    Price: £1,063 - £1,297/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O3CO55, Old Lyme
O3CO55
    Price: £681 - £944/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 1
    • Contact Manager
O3L5, Old Lyme
O3L5
    Price: £679 - £815/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 2
    • Contact Manager

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Holiday rentals you can trust

[ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Caribbean Style Cottage Across from Water & Beach, Shelter Island
Caribbean Style Cottage Across from Water & Beach
Contact Owner
Nightly rate from
£201
Management: Verified owner
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 2
Long Island NY Zen-Like Caribbean Euro Style Secluded Cottage Rental across from Beach and waterfront in Estate section of Shelter Island. A weeks stay at ...
  • Nightly
    £201
  • Weekly
    £1,235 - £2,223
  • Monthly
    £4,538 - £6,792

The following rentals are within 40 kilometres of Shelter Island, Long Island, New York.

O1N19, Old Lyme
O1N19
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 1
For the economy minded, this cottage is one of the best bargainsat the beach. Recreation program for kids, near all the necessities including a new community ...
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CHARMING ARTIST OWNED SHORELINE COTTAGE WITH BEACH, Old Saybrook
CHARMING ARTIST OWNED SHORELINE COTTAGE WITH BEACH
Contact Owner
Nightly rate from
£123
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 2, sleeps 7
Bathrooms: 1
Charming 2 bedroom 1 bath sleep 7. Walk to the private beach in one of the nicest areas alone Ct shoreline.Experience New England’s shoreline year round at ...
  • Nightly
    £123 - £139
  • Weekly
    £741 - £1,111
  • Monthly
    £1,235 - £3,705
O1N49, Old Lyme
O1N49
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 2
Only five houses from sandy beach. Constant favorable comments.Comfortable older remodeled home with modern natural flare.15 miles from New London, USCG, ...
  • Nightly
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  • Weekly
    £946 - £1,311
  • Monthly
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E8A4, Niantic
E8A4
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 2
Enjoy fabulous view of LI Sound and Rocky Neck State Park from this immaculate hilltop home in Giants Neck Beach. A wonderful retreat for winter get-a-ways ...
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O2P35, Old Lyme
O2P35
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 1
A cozy ranch recently refirbished with a beautiful open floor plan..a short 2 minwalk to sandy Hawks Nest Beach. Spacious shaded back yard. Policy: Smoking ...
  • Nightly
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  • Weekly
    £715 - £944
  • Monthly
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O6B57, Old Lyme
O6B57
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 7
Bathrooms: 2
Lovely near waterfront summer home only a few steps to the sand in your toes! Immaculate interior and yard. This fine property is located in a private gated ...
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  • Weekly
    £1,005 - £1,259
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O2CO72, Old Lyme
O2CO72
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 1
BEAUTIFUL WATERVIEW HOME Situated right next to Hawk's Nest Beach. Spacious yard and plenty of parking. Policy: Smoking not allowed, Pets not allowed Minimum ...
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  • Weekly
    £877 - £1,105
  • Monthly
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O2C27, Old Lyme
O2C27
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 1
Summer or Academic winter rental.Centrally cooled and heated. Utilities included summer. An exceptionally offer for a nice house at the sea shore and Hawks ...
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  • Weekly
    £539 - £747
  • Monthly
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O3CO32, Old Lyme
O3CO32
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 1
Nice petit ranch. A corner lot location 2 blocks from a beautiful sandy beach. Available 4 seasons for short vacation get-a-ways. Near the Carosel, shops, ...
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  • Weekly
    £613 - £849
  • Monthly
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O7ST17, Old Lyme
O7ST17
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 1
Spectacular high ocean views. Private sandy/ledge beachfront.A delightful home. Quiet low traffic area situated on Long Island Sound waterfront. Available to ...
  • Nightly
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  • Weekly
    £1,015 - £1,406
  • Monthly
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O2W54, Old Lyme
O2W54
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 5
Bathrooms: 1
A top quality large raised ranch home near private sandy private beach.Accessable to many tourist sites, restaurants , cultural, historic and water related ...
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  • Weekly
    £686 - £951
  • Monthly
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O1S10, Old Lyme
O1S10
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 5
Bathrooms: 1
A delighful family cottage. Ocean View with beach across a sandy lane. Wonderful panoramic views across Long Island Sound and a great sandy town beach. Enjoy ...
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  • Weekly
    £1,605
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O2W84, Old Lyme
O2W84
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 1
Open plan one level cottage directly on the sand. Just step outfront onto your beach blanket. Convenience store nearby. Policy: Smoking not allowed, Pets not ...
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  • Weekly
    £1,078 - £1,494
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O1S47, Old Lyme
O1S47
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 9
Bathrooms: 2
Wonderful remodled direct Long Island Sound Waterfront/sandy beacPrivate road access, unobstructed panoramic views. Family beach area. Policy: Smoking not ...
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  • Weekly
    £1,568
  • Monthly
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Shelter Island Holiday Rental Advice
Shelter Island Hideaway - Absolutely Beautiful- Peaceful
Posted by loveallmyvacations, 11 Sep 2009
... online I found that this vacation rental property on Shelter Island to be very highly rated. All the pictures online and the description made it look and absolutely beautiful and tranquil. I stayed there a few weeks ago and can absolutely say I was not disappointed at all. The place ... more
Posted by smith20Ny, 22 Nov 2009
Thanks for sharing your experience ..it will be helpful ..i also found Vacation Rentals at Hamptons Shelter Island LI NY...you can just visit at http://www.shelterislandhideaway.com/ ... more
Posted by loveallmyvacations, 23 Nov 2009
... too stayed at the Hamptons vacation rental. It ... ... looking for a perfect beach vacation house, right by the water. We already made reservations for the vacation house for ... ... a living room and a home theater! We are hooked and plan to spend many vacations on Shelter Island at the Hideaway ... more
Best play to stay on the island?
Posted by galewindBerkeley, 4 Jun 2009
... of the island so as to recommend where to stay for a relaxing (yet active) vacation for our family? Thank you in advance for any tips. I will post this on the NYC forum as well since it appears that Shelter Island forum not so active (accommodations posts are old ... more
Posted by KathyI2004, 11 Jun 2009
... Harbor. Pridwin looks like it hasn't been updated in quite sometime. The beach is nice, but bring water shoes. The sand is not soft at all, pretty rocky. But still a nice beach. I love Shelter Island, I vacation there every summer. Fortunately family has a home there. Enjoy ... more
Go to Shelter Island Forums »
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns