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3-star hotel Check-in 16:00 · Check-out 11:00

The Ram's Head Inn

Discover The Ram's Head Inn, a 4.4-star gem in Shelter Island Heights, NY. Enjoy elegant accommodations, breathtaking views, and exceptional dining. Ideal for a peaceful getaway, this pet-friendly inn blends charm and comfort, making it the perfect East E

108 S Ram Island Dr, Shelter Island Heights, NY 11965, United States View on map
8.8/10
Very Good Based on 238 recent guest reviews
Free Wi-Fi Free breakfast Free parking Air-conditioned Pet-friendly
What recent guests emphasize

Tranquil island charm with attentive service and scenic views

Guests appreciate the peaceful waterfront setting, friendly staff, and elegant dining options, though some note limited accessibility and a modest cocktail menu.

Guests often praise

  • Peaceful, charming atmosphere with beautiful waterfront views.
  • Welcoming and attentive staff, including personable management.
  • Elevated seasonal menu served in an elegant restaurant setting.
  • Relaxed ambiance complemented by unique touches like pet sheep on the lawn.

Worth knowing

  • No pool, airport shuttle, fitness center, or accessibility features available.
  • The cocktail menu could benefit from more variety and stronger flavor balance.
  • Free Wi-Fi, breakfast, and parking add convenience for guests.
  • Private beach access enhances the waterfront experience.

Best for

  • Visitors seeking a refined yet relaxed island retreat.
  • Couples and travelers who appreciate historic inns with character.
  • Guests wanting easy access to local wineries and nature preserves nearby.
  • Pet owners and families, thanks to pet- and kid-friendly policies.
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About this property

Welcome to The Ram's Head Inn

The Ram's Head Inn transcends the typical experience of a hotel stay, embodying the tranquility and charm of Shelter Island. With a commendable rating of 4.4, this elegant establishment, nestled at 108 S Ram Island Dr, offers both locals and travelers a serene retreat away from the hustle and bustle of daily life.

As Cassandra Leggio aptly describes, "The Ram's Head Inn is a true Shelter Island gem." The picturesque waterfront views and welcoming ambiance instantly immerse you in a sense of peace. The staff’s attentiveness and genuine hospitality elevate every visit, ensuring each guest feels right at home. In a personal note, she often recommends the inn to clients in search of a refined yet relaxed East End experience, corroborating the establishment's reputation for excellence.

Management, led by the amiable Nick, further enriches the experience. His friendly demeanor and insightful recommendations create a comforting environment, as noted by a satisfied guest, Jake Ruehl. Guests remark on the delightful nature of the staff, enhancing the warm, community-oriented feel of the inn.

Visitors flock not only for the accommodations but also for the enchanting setting, where one can admire stunning views while relaxing on the lawn, even engaging with the resident pet sheep. Yet, the culinary offerings stand out as a highlight. The elevated seasonal menu is a testament to the inn's commitment to local flavors and quality, although a guest did mention a desire for a more varied cocktail menu to further complement the delightful dining experience.

The Ram's Head Inn is perfectly positioned for those looking to explore the natural beauty of the area. Just a short distance away are stunning locales such as Orient Beach State Park, known for its serene beachfront and water activities, along with the celebrated Kontokosta Winery and Wölffer Estate Vineyard for wine enthusiasts.

With an array of amenities like free Wi-Fi, complimentary breakfast, and pet-friendly policies, The Ram's Head Inn caters to all types of travelers. This smoke-free oasis promises a tranquil escape, complete with air-conditioned comfort and accessible dining options at the on-site restaurant.

For anyone yearning for a retreat rich in comfort, beauty, and friendly hospitality, The Ram's Head Inn is undoubtedly a destination worth visiting. It encapsulates the essence of Shelter Island—a blend of relaxation, charm, and community that invites guests to return time and again.

Summary compiled by GoHotelly editors from verified guest reviews, partner descriptions and editorial notes.
Facilities & essentials

What's on-site and what you should know before you arrive

The short version: what's available day-to-day, and the key practical details most travelers search for.

Most popular facilities

Free Wi-Fi
Free breakfast
Free parking
Air-conditioned
Pet-friendly
Kid-friendly
Restaurant
Spa
Bar
Smoke-free

Not available at this property

Accessible
Pool
Airport shuttle
Fitness center
Verified guest reviews

What recent guests are actually saying

Reviews from travelers who stayed here in the last 12 months, grouped to help you spot the pattern quickly.

CL(
Cassandra Leggio (Cassandra) Jun 07, 2025
10

⭐⭐⭐⭐⭐ The Ram’s Head Inn is a true Shelter Island gem—peaceful, elegant, and full of charm. From the waterfront views to the welcoming staff and elevated seasonal menu, every visit feels like a retreat. As a local real estate professional, I often recommend it to clients seeking a refined yet relaxed East End experience. A beautiful destination that perfectly captures the essence of Shelter Island. — Cassandra Leggio, Licensed Real Estate Salesperson Curating Legacy, Refining Worlds

JR
Jake Ruehl May 19, 2025
10

Nick, the manager makes his place feel like home. Listen to his recommendations, you will not be disappointed. Everyone else who works there is truly a delight. I'm just terrible with names otherwise I'd name them all.

JGS
Jackie Gordon Singing Chef Apr 10, 2025
8.0

Even if you're not staying at the inn you should pop in for a drink. It's a beautiful spot. You can sit on the lawn and take in the view and admire the pet sheep. I would love to see a more varied cocktail menu. My Bees Knees cocktail was a bit short on that Bees. It definitely needed more honey to balance it. My friend's enjoyed their RHI 75 cocktails.

Location & neighborhood

Where you'll find The Ram's Head Inn

Shelter Island Heights, New York, USA

Set in waterfront grounds, this genteel island inn dating from 1929 is 5 miles from sheltered Smith Cove and 6 miles from the Mashomack Preserve, a coastal nature reserve. The North Ferry dock is 4 miles away.

  • Long Island MacArthur Airport 1 hr 39 Car
  • Tweed New Haven Airport 2 hr 57 Car
Things to do nearby

Worth the walk or a quick ride

Curated spots travelers usually pair with a stay in New York. Distances are rough real-world times, not straight-line.

Wölffer Estate Vineyard 703 reviews

Wölffer Estate Vineyard

139 Sagg Rd, Sagaponack, NY 11962, United States

4.3 · Vineyard
Kontokosta Winery 532 reviews

Kontokosta Winery

825 North Rd, Greenport, NY 11944, United States

3.8 · Winery
Sparkling Pointe Vineyards & Winery 333 reviews

Sparkling Pointe Vineyards & Winery

39750 County Rd 48, Southold, NY 11971, United States

4.5 · Winery
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