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An understated colonial-style home is the perfect setting for a Northeastern getaway. It's reminiscent of a family heirloom, with history seeping through the walls. Situated on a bluff with views of the Connecticut shoreline, the home sits atop sprawling private acres dotted with centuries-old trees. A typical day here will take you straight back to the carefree life of childhood – gather in the kitchen for pancakes before slipping on your sandals to walk down the lawns to your very own private beach, before spending the evening playing games around the fireplace in a cosy living room. Choose a new bedtime read from the home's library or brainstorm your own novel in the study – perfect for remote workers. Port Jefferson is only a short twelve-minute drive away, and you’d be remiss not to stop at the farmers market and bring back fresh produce to cook, reminding you of the pleasures of a simpler life.


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What to expect


Highlights

Access your very own private beach directly behind the house

Access your very own private beach directly behind the house

Gather your ensemble for a meal in the grand dining room

Gather your ensemble for a meal in the grand dining room

Take your pick from a selection of board games in the cosy living room

Take your pick from a selection of board games in the cosy living room

Brainstorm your novel while gazing out at the moody sea

Brainstorm your novel while gazing out at the moody sea

Get lost in  a book in the shade of a hundred-year-old tree

Get lost in a book in the shade of a hundred-year-old tree

Test out the telescope on a clear day

Test out the telescope on a clear day

Like what you see? Explore more of this home

Home truths

    Once you get into the traditional Suffolk County town the best way to get around is by car – there's ample parking at the house

    Two rooms in the basement are used for the host's storage and are not for guest access

    The wi-fi is inconsistent in some parts of the home

    Guests must be willing to put the rubbish out on the pavement on Monday and Thursday evenings

    Your host provides children's books and toys

    This is a self-check-in home with keypad access

About this stay


Amenities

Outdoor seating

Desk / workplace

Laptop friendly workspace

Wi-fi

Air conditioning

Parking available

Bedrooms & bathrooms

5 bedrooms, 6 beds

3 bathrooms

Extras


VIP services

Arrange a chef

Restaurant reservations

Extras are subject to availability. Please enquire with your host.

Local guide


Explore the area

Local restaurants, cafes, museums, sites and activities, recommended by our community of hosts and travel experts

Explore the Parrish Art Museum

Explore the Parrish Art Museum

Immerse yourself in contemporary American art at this architecturally stunning museum. Enjoy temporary exhibits, including works by Audrey Flack, Frida Kahlo, and William Merritt Chase. Free parking and easy access make it a must-visit on Long Island.

Paddle through Shelter Island with Venture Out

Paddle through Shelter Island with Venture Out

Venture Out Paddle Board Rentals offers an unforgettable experience exploring Shelter Island's waters. With knowledgeable guides, top-notch equipment, and excellent service, it's the perfect way to stay active and have fun on your holiday.

Dine at Bell & Anchor

Dine at Bell & Anchor

Upscale, seafood-centric New American cooking served in a bustling, nautical setting with bay views. Enjoy delicious drinks, incredible oysters, and stunning entrees. A great restaurant to explore in Southampton and Sag Harbor.

Stay at Shelter Island House

Stay at Shelter Island House

Quaint country inn with casual-chic rooms, outdoor lounge, bakery, pool, and friendly staff. Enjoy private beaches, biking, and good food nearby. A lovely weekend getaway.

Sail the Stunning Bays with Sag Harbor Sailing

Sail the Stunning Bays with Sag Harbor Sailing

Sag Harbor Sailing Inc. is a passionate team of experienced sailors offering boat rentals, sailing lessons, and overnight charters. With well-maintained boats and knowledgeable instructors, this is the perfect activity to explore the Hamptons from a new perspective.

Dine at Calissa Hamptons

Dine at Calissa Hamptons

Experience chic coastal dining with exceptional Mediterranean cuisine, fine wine, and craft cocktails. Enjoy the beautiful ambience and accommodating service at this amazing restaurant.

Dine at Noah's

Dine at Noah's

Experience the best of New American cuisine with a focus on local ingredients at this modern restaurant and bar. Indulge in incredible seafood dishes, from lobster rolls to tuna poké bowls, and enjoy generous portions and stellar service.

Savour the Scenic Views at Kontokosta Winery

Savour the Scenic Views at Kontokosta Winery

Indulge in a delightful experience at Kontokosta Winery, offering breathtaking views of the sound. Sip on exquisite wines and relish delectable snacks amidst the stunning surroundings of this charming establishment.

Explore Mitchell Park & Marina

Explore Mitchell Park & Marina

A perfect beach for families with little kids, featuring a delightful carousel ride and a picturesque boardwalk. Enjoy the vibrant atmosphere with concerts and dancing, or simply take a leisurely walk around the beautiful marina.

Savour Fresh Oysters at Little Creek Oyster Farm & Market

Savour Fresh Oysters at Little Creek Oyster Farm & Market

Shucked oysters & local beers served in a snug harborside cottage with a market & outdoor seating. Great atmosphere, delicious drinks, and an A+ waterfront location.

Explore the Rich Political History of Shelter Island

Explore the Rich Political History of Shelter Island

Immerse yourself in the fascinating political history of Shelter Island, a locality known for its significant role in shaping the region's governance. Discover historical landmarks and gain a deeper understanding of the area's past.

Enjoy Foster Memorial Beach

Enjoy Foster Memorial Beach

With its beautiful beach, calm and clear water, Foster Memorial Beach is perfect for small sail sports or simply relaxing with a walk or run. It's a great option for a swim without turning into an ice cube and offers wide space to enjoy the beach without feeling crowded. Don't miss the stunning sunsets!

Booking policies


House Rules

Children welcome (1-12 years)

Infants welcome (under 12 months)

No pets

No parties or events

No smoking

Good to know

Arrival from 14:00

Departure before 13:00

Air con

Wifi

Cancellation policy

  • Up until

    5

    days

    Cancel at least 5 days before your check-in date for a full refund.

  • Not eligible for a refund once your check-in date is under 5 days away.

Host


This home is managed by Jonathan

This home is managed directly by its owner who will be your point of contact before and during your stay. Jonathan is always up for a little adventure. However, he values the home comforts and is on hand to make your trip to New York as stress-free and easy as possible.

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This home is nominated for the Plum Guide Award.

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  • Every home scrutinised by experts, they have to meet our standards.
  • Hosts we knowHigh-quality hosting, with track records of high-quality hosting.
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  • Rated ‘Excellent’ on Trustpilot, delivering exceptional service before, during and after your stay.