Shelter Island Romantic Accommodation

We selected the 928 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Shelter Island

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Minutes away from East Hampton Village, this beautiful Sag Harbor home is ideal for sun worshippers and golfers alike. The Sag Harbor Golf Course is a stone's throw, and Havens Beach, among others, is reachable by car in minutes.

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

This quintessential clapboard home in Sag Harbor is sure to pique the interest of travellers looking for a relaxing stay in the Hamptons. With its close proximity to the coast, including Haven's beach, the home is conveniently located for exploring the area.

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light.


We selected the top 3% holiday homes in Shelter Island Romantic Accommodation

Explore the 928 most perfect homes in our collection

View on map

Most popular homes in Shelter Island

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

View all

Check upcoming rates & availability for Shelter Island Romantic Accommodation


Frequently asked questions

Discover the most romantic accommodation in Shelter Island. We’ve handpicked homes that are perfect for two, in soulful neighbourhood locations with characterful living spaces, sumptuous bedrooms and luxurious bathrooms. Book today and enjoy a short or extended stay in the most romantic accommodation that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

Search Our Collection