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Charming, Historic Cottage

Photo gallery for Charming, Historic Cottage

A two-story house with a porch, a covered patio, and a dining area with outdoor furniture.
A dining area with a round table and chairs, a chandelier, and a view into the kitchen.
A dog standing on a doormat at a door with a window, a hat, and a curtain.
A bedroom with a large bed, a small table, and a chair.
A living room with a fireplace, a sofa, a coffee table with books, and a window with a view of trees.

Reviews

10 out of 10
Exceptional
Near the sea, this 3-bedroom cottage accommodates 6 guests with 2 bathrooms. Enjoy nearby fishing, birdwatching, and surfing activities. The marina offers water activities. Explore attractions like Sylvester Manor and Havens House in the charming village setting.
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Kitchen
  • Washing machine
  • Air-conditioning
  • Internet access
  • Fireplace
  • Dryer

Explore the area

View in a map
Shelter Island, NY
  • Place, Shelter Island Historical Society
    ‪11 min walk‬
  • Place, Havens House
    ‪11 min walk‬
  • Place, Shelter Island Whale's Tail
    ‪14 min walk‬
  • Airport, Westhampton, NY (FOK-Francis S. Gabreski)
    ‪60 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Dining area

About this property

Charming, Historic Cottage

Lovely three bedroom cottage centrally located. Cook's kitchen, cozy living room with fireplace, two bathrooms, southern light, and large, private yard. The perfect spot to read, relax, prepare meals and explore the natural beauty of Shelter Islabd. The cottage is close to all island beaches, nature preserve and restaurants. All of the charm and character of an original house on the island dating to the 1860’s but lovingly updated and very comfortable.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3525659
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Shelter Island

Located in Shelter Island, this cottage is in a rural area and near the beach. The area's natural beauty can be seen at The Hamptons Beaches and East Hampton Main Beach. Shelter Island Whale's Tail and East End Seaport Maritime Museum are also worth visiting. Discover the area's water adventures with waterskiing and sailing nearby, or enjoy the great outdoors with horse riding and cycling.
View more Cottages in Shelter IslandOpens in a new window
Map
Shelter Island, NY

What's nearby

  • Shelter Island Historical Society - 11 min walk - 1.0 km
  • Havens House - 11 min walk - 1.0 km
  • Shelter Island Whale's Tail - 14 min walk - 1.2 km
  • Sylvester Manor - 14 min walk - 1.2 km
  • Kontokosta Winery - 26 min drive - 7.9 km

Getting around

  • Greenport Station - 23 min drive
  • East Hampton, NY (HTO) - 41 min drive

Restaurants

  • ‪Claudio’s Waterfront - ‬24 min drive
  • ‪Aldo's - ‬24 min drive
  • ‪Lucharitos - ‬24 min drive
  • ‪Pridwin Hotel - ‬5 min drive
  • ‪Port Bar & Grill - ‬23 min drive

Frequently asked questions

Is Charming, Historic Cottage pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Charming, Historic Cottage ?

As of 28 Aug 2026, prices found for a 1-night stay for 2 adults at Charming, Historic Cottage on 7 Sept 2026 start from £8,441, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at Charming, Historic Cottage ?

Check-in begins at 4:00 PM.

What time is check-out at Charming, Historic Cottage ?

Checkout is at 11:00 AM.

Where is Charming, Historic Cottage located?

Situated by the sea, this cottage is 0.6 mi (1 km) from Havens House and 2.8 mi (4.4 km) from The Hamptons Beaches. Shelter Island Whale's Tail and Shelter Island Historical Society are also within 15 minutes.

About the host

Hosted by Rebecca Blair

Host profile image
I am currently training for yoga certification and have worked in fashion for many years.

Why they chose this property

If you appreciate historical homes with a sense of place on an idyllic, charming island, then the 'tree house' is for you.

What makes this property unique

Historical Architecture
Beautiful Decor
Gorgeous Light
Fireplace
Cooks Kitchen
Front Porch
Large, private yard

Languages:

English
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