10 guests
-
5 bedrooms, 6 beds
4 bathrooms
Ask the host anything
Do you have a question about this home or the local area?
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.
The Plum Promise
- No time for average – We reject thousands of homes worldwide, so you don't have to.
- Hosts we know – With track records of high-quality hosting.
- Rated ‘Excellent’ on Trustpilot – Exceptional service before, during and after your stay.
Ask the host anything
Do you have a question about this home or the local area?
What to expect
Highlights
Explore Wooley Pond and the area beyond from this beautiful home
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
Enjoy a spa day with the master suite's private sauna and jacuzzi
Wake up to the stunning views from the master suite
Start your morning with a workout in the gym
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
Dryer
Swimming pool
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
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
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
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
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
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
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
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
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
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
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.
Property classified as: common.undefined.propertyTypes.non-hotel.name
This home is nominated for the Plum Guide Award.
- Great hosts, not just great homes – We reject homes managed by hosts who don’t meet our standards of excellence.
The Plum Promise
- Every home scrutinised by experts, they have to meet our standards.
- Hosts we knowHigh-quality hosting, with track records of high-quality hosting.
- Impeccably clean, well maintained homes.
- Peace of mind in the rare event your host cancels.
- Rated ‘Excellent’ on Trustpilot, delivering exceptional service before, during and after your stay.