8 guests
-
5 bedrooms, 6 beds
3 bathrooms
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
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
Brainstorm your novel while gazing out at the moody sea
Get lost in a book in the shade of a hundred-year-old tree
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
Washing machine
Dryer
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
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
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
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
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
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
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
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
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
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
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
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
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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- Rated ‘Excellent’ on Trustpilot, delivering exceptional service before, during and after your stay.