Name: Pier Blue Inn Old Saybrook - Essex
Price range: $114 total
Rating: 8

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island

A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Wades Beach and Sunset Beach.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Sunset Beach, some noteworthy sights in the nearby area.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Wades Beach and Sunset Beach.

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$1,045 nightly

$1,194 total

Jul 8 - Jul 9

Total with taxes and fees

Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...

8.4/10 Very Good! (816 reviews)

"Great experience."

Reviewed on Jun 25, 2026

Offshore Montauk

71 S Emerson Ave Montauk NY

$698 nightly

$798 total

Jul 5 - Jul 6

Total with taxes and fees

Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point are located ...

9.2/10 Wonderful! (145 reviews)

"best staff"

Reviewed on Jun 28, 2026

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

$99 nightly

$114 total

Jul 8 - Jul 9

Total with taxes and fees

Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...

8/10 Very Good! (1,002 reviews)

"staff and parking"

Reviewed on Jun 22, 2026

See all 4,734 properties in Shelter Island

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.

Montauk Manor

236 Edgemere St. Montauk NY

Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...

North Fork Resort

690 Queen St Greenport NY

Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...

9.2/10 Wonderful! (25 reviews)

"We loved our stay at the North Fork Resort. We would definitely recommend. Family & pet friendly to the max! Any hiccups we had with our stay were resolved without hesitation or annoyance by the staff. They were incredibly accommodating. The pool area was spacious and clean but the pool itself was ..."

Reviewed on Jun 26, 2026

Cliffside Resort Condominiums

61475 Route 48 (North Road) Greenport NY

Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...

9/10 Wonderful! (263 reviews)

"Lovely condo, set back from the coast but gorgeous sea view. Brilliant covered external seating area which shades form the sun and the rain. Condo was very nicely decorated."

Reviewed on Jun 28, 2026

See all properties in Shelter Island

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.