Shelter Island Guest Houses

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Guest Houses in Shelter Island

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY

$266 nightly

$303 total

Nov 5 - Nov 6

Total with taxes and fees

Located in Hampton Bays, Hampton's Vacation Inn is within a 15-minute drive of Shinnecock Hills Golf Course and Ponquogue Beach.

Pool

Pet friendly

House on Chase Creek

3 Locust Avenue Shelter Island Heights NY

$185 nightly

$211 total

Nov 2 - Nov 3

Total with taxes and fees

With a stay at House on Chase Creek in Shelter Island Heights (The Heights), you'll be within a 5-minute drive of Shelter Island Country Club and Sylvester Manor.

Parking included

Free WiFi

New and Modern Bridgehampton Accommodations

Bridgehampton NY

$466 nightly

$532 total

Oct 25 - Oct 26

Total with taxes and fees

With a stay at this guesthouse in Bridgehampton, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and South Fork Natural History Museum and Nature Center.

Pet friendly

Free WiFi

Steps from the Ocean

Montauk NY

When you stay at this guesthouse in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Pet friendly

Free WiFi

Charming Southampton Village Guest Home -Walk to Beach, Restaurants, Shops

Southampton NY

$857 nightly

$979 total

Oct 24 - Oct 25

Total with taxes and fees

When you stay at this guesthouse in Southampton, you'll be by the sea, a 5-minute drive from The Hamptons Beaches and 7 minutes from Cooper's Beach.

Pool

Free WiFi

Victorian Seasons Stirling

857 NY-25 Greenport NY

Located in Greenport, Victorian Seasons Stirling is within a 15-minute walk of Kontokosta Winery and Greenport Farmers' Market.

Parking included

Free WiFi

The North Fork Loft

Peconic NY

Located in Peconic, this guesthouse is on the waterfront, a 1-minute drive from Goldsmith's Inlet Park and 6 minutes from Sannino's Bella Vita Vineyard.

Pool

Air conditioning

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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.