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  • 10 guests

  • 5 bedrooms

  • 4 bathrooms

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Artists have long been drawn to Wooley Pond. The painter Nicolai Cikovsky had a cottage in the area – one look at the landscape and you’ll understand why. This elegant home has an acre of gardens and sits right on the waterfront. Budding artists can set up an easel and paint the landscape from the beautifully manicured lawns, or you can make the most of the private dock and take your boat out for a day on the water. If that all sounds too energetic, sun loungers by the heated pool are perfect for a lazy afternoon, and you’ve got a sauna and jacuzzi inside to fully immerse you into relaxation mode. The glass-enclosed dining area and picture windows in the living room mean you don’t have to leave the view behind when you head inside, and as you sink into the sofas there’s a glorious vaulted wood beam ceiling and tiled fireplace to admire as well. You’ll find characterful touches thrown in the mix too – from the artwork, to a piano, to colourful pendant lights and a wet bar in the expansive master suite. At every turn, this home is sure to delight.


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What to expect


Highlights

Explore Wooley Pond and the area beyond from this beautiful home

Explore Wooley Pond and the area beyond from this beautiful home

Dive into the heated pool or admire the views from the poolside loungers

Dive into the heated pool or admire the views from the poolside loungers

Admire the vaulted wood beam ceiling and tiled fireplace as you relax in the living room

Admire the vaulted wood beam ceiling and tiled fireplace as you relax in the living room

Enjoy a spa day with the master suite's private sauna and jacuzzi

Enjoy a spa day with the master suite's private sauna and jacuzzi

Wake up to the stunning views from the master suite

Wake up to the stunning views from the master suite

Start your morning with a workout in the gym

Start your morning with a workout in the gym

Play a game of tennis at the private community tennis courts nearby

Play a game of tennis at the private community tennis courts nearby

Like what you see? Explore more of this home

Home truths

    The home has a private dock that can accommodate one large and one small boat

    The gym, jacuzzi, sauna and a private office are located in the master suite

    The host will consider allowing pets in the home – please ask when you're booking

    The home is in a private community and there are also tennis courts nearby that you'll be able to use

    Due to the climate of the northeastern U.S., outdoor pools will typically only be available for use from Memorial Day to Labor Day – if you are staying outside of this period and would like to use the pool, please check with the host before booking

    If you are planning to stay for longer than a week, there will be mandatory weekly cleaning for an additional charge

About this stay


Amenities

Gym

Sauna

Wi-fi

Air conditioning

Pets allowed

Washing machine

Bedrooms & bathrooms

5 bedrooms, 6 beds

4 bathrooms

Extras


VIP services

Airport pick up

Daily cleaning

Fridge fills

Additional fees

  • There may be some extra fees to pay here, such as charges for utilities, final cleaning fees, city tax and security deposits – all of which you may need to pay in cash to the homeowner. Please reach out during the booking process to confirm.

Additional fees subject to a 3.5% handling charge.

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

Local guide


About Southampton

The most well-known and established town of this luxurious city escape, chances are, when you imagine the iconic Hamptons, you’re imagining something pretty close to Southampton. Stately homes dating back centuries, rolling lawns, rosé all-day, celebrities and manicured hedges – Southampton is the postcard image for the glamorous folklore surrounding the infamous South Fork of Long Island. Explore the estates of Gin Lane and Meadow Lane, nicknamed Billionaire Row, and...

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.

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.

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.

Explore Bridge Gardens

Explore Bridge Gardens

A local gem, Bridge Gardens offers a peaceful and beautiful place to walk around. Enjoy the stunning gardens, cool artwork, and the opportunity to spot growing produce. Plenty of space for everyone!

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!

Indulge in Homemade Treats at Bridgehampton Candy Kitchen

Indulge in Homemade Treats at Bridgehampton Candy Kitchen

Step into this old-fashioned luncheonette and enjoy delicious homemade ice cream, classic desserts, and comforting comfort food. With a nostalgic coffee shop vibe, it's the perfect place to create lasting family memories in Bridgehampton.

Stay at Baron's Cove

Stay at Baron's Cove

Chic waterfront getaway with cozy fires, live music, delicious food, and stunning sunset views. Highly recommended for a relaxing stay in Sag Harbor. Kid-friendly grounds and top-notch service make it a perfect choice for families.

Dine at Tutto il Giorno Sag

Dine at Tutto il Giorno Sag

Experience the incredible flavors of Italian cuisine at this year-round restaurant. Enjoy a romantic and homey ambiance, friendly staff, and flavorful dishes like the Risotto and Tortelli.

Explore the Historic Charm of Sag Harbor

Explore the Historic Charm of Sag Harbor

Immerse yourself in the rich history and quaint charm of Sag Harbor. This locality, known for its political significance, offers a unique experience filled with historical landmarks and a vibrant community.

Enjoy Wine and Scenic Views at Wölffer Estate Vineyard

Enjoy Wine and Scenic Views at Wölffer Estate Vineyard

Indulge in delicious food and wine while taking in the beautiful vineyard views. With indoor and outdoor seating options, this stylish winery is a must-visit for wine enthusiasts and those seeking a memorable experience.

Booking policies


House Rules

Infants welcome (under 12 months)

Children welcome (1-12 years)

Pets welcome

No parties or events

No smoking

Good to know

Arrival from 15:00

Departure before 11:00

Air con

Wifi

Cancellation policy

  • Up until

    60

    days

    Cancel at least 60 days before your check-in date for a 50% refund.

  • Not eligible for a refund once your check-in date is under 60 days away.

Host


This home is managed by Bryan

This home is managed directly by a business. A member of their staff will be your point of contact before and during your stay. Bryan and his team are vacation experts, especially when it comes to The Hamptons and surrounding towns. With years of experience, they’re with you every step of the vacation rental process – and they take pride in giving their guests a personalised experience to remember.

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This home is nominated for the Plum Guide Award.

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