Book Guest Houses in Shelter Island, NY

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Top Guest Houses in Shelter Island

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY

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This guesthouse features an outdoor tennis court and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a picnic area, and express check-out are also on offer.

Pool

Pet friendly

Steps from the Ocean

Montauk NY

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This guesthouse featured laundry facilities and barbecue grills.

Pet friendly

Free WiFi

House on Chase Creek

3 Locust Avenue Shelter Island Heights NY

$104 nightly

$119 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

Free self parking is available and the guesthouse's front desk is staffed around-the-clock. WiFi in public areas is free. A terrace, a garden, and luggage storage are also on offer.

Parking included

Free WiFi

Victorian Seasons Stirling

857 NY-25 Greenport NY

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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a library are also on offer.

Parking included

Free WiFi

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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.

Top hotels in Shelter Island

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT

$312 nightly

$359 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

9.4/10 Exceptional! (1,014 reviews)

Shelter Island Guest Houses essential information

Accommodation	6 Guest Houses
Lowest Price	$89
Highest Price	$496
Popular accommodation	Hampton's Vacation Inn, Steps from the Ocean , House on Chase Creek, Victorian Seasons Stirling