Book Guest Houses in Shelter Island, NY

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Guest Houses in Shelter Island

Hampton's Vacation Inn

177 West Montauk Highway, Hampton Bays, NY

$126 nightly

$144 total

Oct 19 - Oct 20

Total with taxes and fees

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

New and Modern Bridgehampton Accommodations

$384 nightly

$438 total

Oct 5 - Oct 6

Total with taxes and fees

This guesthouse features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

House on Chase Creek

3 Locust Avenue, Shelter Island Heights, NY

$185 nightly

$211 total

Nov 3 - Nov 4

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

Steps from the Ocean

Get rates

This guesthouse featured laundry facilities and barbecue grills.

Pet friendly

Free WiFi

Victorian Seasons Stirling

857 NY-25, Greenport, NY

Get rates

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

Don't see what you're looking for?

See all available properties in Shelter Island

View all properties

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

Montauk Blue Hotel

108 South Emerson Avenue, Montauk, NY

$148 nightly

$170 total

Nov 2 - Nov 3

Total with taxes and fees

9.2/10 Wonderful! (145 reviews)

Shelter Island Guest Houses essential information

Accommodation	6 Guest Houses
Lowest Price	$91
Highest Price	$438
Popular accommodation	Hampton's Vacation Inn, New and Modern Bridgehampton Accommodations , House on Chase Creek, Steps from the Ocean , Victorian Seasons Stirling