Head of the Harbor Guest Houses

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Guest Houses in Head of the Harbor

The Madison Fire Island Pines

22 Atlantic Walk, Sayville, NY

When you stay at The Madison Fire Island Pines in Sayville, you'll be within the region of Fire Island Lighthouse.

Guesthouse duplex apartment with gorgeous pool & gardens!

With a stay at this guesthouse in Bellport (North Bellport), you'll be a 3-minute drive from Great South Bay and 7 minutes from Carmans River.

3 private bedrooms with Pool Holiday home 3 BestStayz.1

Centerport, Centerport, NY

When you stay at 3 private bedrooms with Pool Holiday home 3 BestStayz.1 in Centerport, you'll be near the beach, within a 5-minute drive of Vanderbilt Museum and Centerport Beach.

Linwood Whole House

296 Linwood Ave, Bridgeport, CT

With a stay at Linwood Whole House in Bridgeport (West End - West Side), you'll be within a 10-minute drive of Fairfield University and Bridgeport Downtown South Historic District.

Fairfield Whole House

210 Fairchild Ave, Fairfield, CT

With a stay at Fairfield Whole House in Fairfield, you'll be within a 5-minute drive of Fairfield University and Bridgeport Downtown South Historic District.

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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.