Hotels in Shelter Island
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Where to stay in Shelter Island?
2. Shelter Island House
Shelter Island House
3. House on Chase Creek
House on Chase Creek
5. Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach Bungalows
6. The Shoals Suites and Slips
The Shoals Suites and Slips
7. Sound View Greenport
Sound View Greenport
8. The Harbor Front Inn
The Harbor Front Inn
9. North Fork Resort
North Fork Resort
10. American Beech Hotel
American Beech Hotel
11. The Menhaden
The Menhaden
12. Cliffside Resort Condominiums
Cliffside Resort Condominiums
13. Oyster Estate
Oyster Estate
14. The Pridwin Hotel
The Pridwin Hotel
15. Sag Harbor Inn
Sag Harbor Inn
16. Faraway Sag Harbor
Faraway Sag Harbor
17. Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
18. Clinton Motel
Clinton Motel
19. Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
Go beyond your typical stay in Shelter Island
Top neighborhoods in Shelter Island
Silver Beach
Shell Beach beckons with pristine shorelines and dreamy water views along Shelter Island's peaceful coast. Silver Beach's waterfront charm shines through weathered shingled cottages with white trim and classic New England porches. Pack your swimsuit for calm waters perfect for kayaking and swimming, or bring binoculars for spectacular birdwatching. Getting around requires a personal vehicle, though the neighborhood is wonderfully walkable once you arrive. Most visitors stay in vacation rentals with private beach access. For dining and shopping, you'll need to venture to other parts of Shelter Island or pack provisions for self-catering.
Menantic Creek
Menantic Creek offers a dreamy slice of Shelter Island life where waterfront homes nestle among oak trees. Here, your days revolve around peaceful paddles along the winding creek, spotting ospreys overhead, and unwinding on private docks. Wade's Beach and Shell Beach provide perfect spots for collecting shells or simply watching the waves roll in. When hunger strikes, you'll need to venture beyond the neighborhood to other parts of Shelter Island. Vacation rentals dominate the accommodation scene, with classic Hamptons-style homes featuring cedar shingles and wraparound porches. A personal vehicle is essential for exploring, though cycling the quiet streets makes for lovely morning adventures.
Coecles Harbor
Coecles Harbor combines peaceful seclusion with maritime charm on Shelter Island's eastern shore. Weathered wooden docks extend into calm waters where luxury yachts bob alongside working fishing boats. Menhadden Lane Beach offers pristine shoreline access, while scenic waterfront paths wind past New England-style cottages with classic shingle siding and white trim. Summer brings waterfront dining with fresh seafood and sunset cocktails, though most establishments close early. Accommodation options include upscale vacation rentals and boutique inns with private docks. The area remains blissfully quiet year-round, with activities centered around kayaking, paddleboarding and sailing in the protected waters of Peconic Bay.
Hay Beach
Hay Beach offers a peaceful escape on Shelter Island with three sides of pristine waterfront. This quiet peninsula is dotted with private homes and beach access points where you can dip your toes in the clear waters. Menhadden Lane Beach beckons sunbathers and swimmers, while nearby Gardiner's Bay Country Club provides scenic views for those who venture beyond the neighborhood. Vacation rentals and private cottages make up most accommodations, with classic Hamptons-style architecture blending into the natural landscape. Getting around requires planning as there's limited public transit, though the small peninsula is perfect for relaxing walks along the shoreline paths where the only sounds are gentle waves and wildlife.
Shorewood
Shorewood offers an idyllic escape on Shelter Island with pristine beaches and coastal charm. Wade's Beach beckons with soft sand and gentle waves, while tree-lined streets wind through charming summer cottages and upscale vacation homes. Nature lovers can explore nearby Mashomack Preserve or stroll along scenic shoreline paths with breathtaking water views. The neighborhood is predominantly residential with minimal commercial activity. Visitors typically self-cater or venture to Shelter Island Heights for dining options. Vacation rentals with classic Hamptons-style architecture dominate the accommodation scene. Getting around is best done on foot or by car, with the peaceful atmosphere making it perfect for those seeking a tranquil waterfront retreat.
Top landmarks in Shelter Island
Wades Beach
Shell Beach
Mashomack Preserve
Shelter Island Historical Society
Gardiner's Bay Country Club
Shelter Island Whale's Tail
Menhadden Lane Beach
Havens House
Learn more about Shelter Island
Between the North and South Forks of Long Island, this ferry-accessible haven offers a quieter alternative to Hamptons glitz. Wade into the gentle surf at Crescent Beach or spread a towel at Sunset Beach, where the day's end brings spectacular skies. The Mashomack Preserve invites exploration with trails winding through 2,000 acres of pristine woodlands and tidal creeks. History buffs can discover island lore at the Shelter Island Historical Society's Havens House. Shell Beach provides perfect shell-hunting opportunities away from crowds. For the full experience, rent a bicycle – the island's modest size makes two wheels the ideal way to discover hidden coves and charming corners that weekend warriors from Manhattan haven't yet claimed.
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Check out reviews of Shelter Island hotels guests love
Montauk Manor
"We loved the room and views. Will definitely come back."
Water's Edge Resort & Spa
"It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return."
Ocean Surf Resort
"The view is the best! Beach is beautiful. Rooms are clean however the rooms need some maintenance done. Holes in doors and curtain rods almost falling down . Air conditioning units need to be replaced. Fans on high all the time and turn on and off every 10 min. Had to turn off at night . The staff are very helpful and courteous. We will return again"
Marram
"Amazing hip on the beach Cool best food anywhere"
The Atlantic Hotel
"I had room facing the busy street, but the room was well insulated and I did not hear the traffic from outside. Also, the floor plan was very functional. Linen was clean CLEAN, bed was SO comfortable And the amenities of small fridge, coffee maker, iron, -and 2 water bottles provided with each room clean was especially helpful. Parking spaces were wide with ample space to unload and open passenger doors."
Sound View Greenport
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."
Sun N Sound
"Very nice and clean. Pool was excellent. Only complaint was that the bathroom sink and shower drains were slow to drain. I'll give it a 8/10"
North Fork Resort
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
Zey Hotel
"My Husband Phil & I had the Best Stay. Very Quaint Hotel, just a couple of blocks from waterfront.Absolutely spotless, so many sitting areas, Coffee, tea water and ice available 24-7. Our room was spotless, decorated so well. We also had a balcony. James and all staff were so Pleasant and so accommodating. Can't wait to return for another stay. Thank you James .. Phil & Jenn"