FOR RENT
Welcome to Fishers Island, New England’s Best Kept Secret
We are as excited to introduce new people to Fishers Island as we are to welcome back old friends. We find great joy to hear how within hours of arriving, the stresses of mainland life drain away.
Most rental houses include an additional utility and cleaning charge. Come experience all that island life has to offer!
Please call us for personalized assistance with your rental booking and for additional listings that may not be featured.
(860) 331-1510
e-mail info@shuttersandsails.com
(Search by rental NAME, DATE, ROOM #, etc.)
PLEASE NOTE: We are in the process of updating 2026 availability and pricing.
| Rental Name |
Sleeps | BR | Area | Description | Weekly Rental |
Avail Cal |
|
|---|---|---|---|---|---|---|---|
 |
Finan by the Sea | 10 | 5 | West End | Waterfront retreat overlooking West Harbor | $17,000/week | |
 |
Owls Nest | 10 | 5 | West End | overlooking West Harbor and the Long Island Sound | Call for 2026 Pricing | |
 |
Harbor View Cottage | 6 | 3 | West End | Waterfront views of West Harbor | $7,500/week | |
 |
The Pumphouse | 5 | 2 | West End | waterfront with private dock and beach | $6,000/week | |
 |
Lake House | 16 | 8 | East End | spacious, private, lakefront |
$13,500/week | |
 |
Pirates Cove Cottage | 4 | 2 | West End | Waterfront | $4,750/week | |
 |
Oyster Barn | 10 | 5 | East End | Breathtaking water views | $15,000/week | |
 |
Hydrangea House | 4 | West End | 4 Bed cottage near the village | Call for 2026 pricing | ||
 |
Oceanhill | 6 | 3 | West End | Enjoy expansive views of the coast from this private and contemporary West End home. | Call for 2026 pricing | |
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Leeway | 7 | 4 | West End | Waterfront, Private Beach | $10,000 /week | |
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Hill Cottage | 9 | 5 | West End | tucked into North Hill | Call for 2026 pricing | |
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Milliken House | 10 | 4 | East End | waterviews, private | $10,000/week | |
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Love Shack | 6 | 3 | East End | Water View | Call for 2026 pricing | |
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Hanes Flinn House | 10 | 5 | West End | Large, updated house | Call for 2026 pricing | |
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FI Getaway | 8 | 4 | West End | quiet house walking distance to dock beach | $6,000/week | |
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Braun House | 6 | 3 | West End | waterfront, stunning harbor views |
$7,600/week | |
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Yellow House | 8 | 4 | West End | updated Officer's Row house, water view |
Call for 2026 pricing | |
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Just Right | 8 | 4 | West End | updated house in the village |
Call for 2026 pricing | |
 |
The Laughing Place | 10 | 7 | West End | large house in the Village |
$7,000/week | |
 |
Osprey Hill | 10 | 5 | East End | secluded house, water view |
Call for 2026 pricing | |
 |
Highball | 8 | 3 | East End | contemporary near the Big Club, water views |
$7,500/week | |
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Treetops | 5 | 3 | West End | comfortable cottage near village |
$4,000/week | |
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Holiday Hill | 10 | 5 | West End | House in the Village | $8,000/week | |
 |
Rabbit Run Cottage | 3 | 1 | East End | secluded cottage,water views | Call for 2026 pricing |