Resort-Style Southold Retreat with Private Pool, Guest House, and Chic. | House in Southold

Please note that a reservation for this property needs to be approved before it is confirmed.
The Southold Escape
Resort-Style Southold Retreat with Private Pool, Guest House, and Chic Indoor-Outdoor Living
4BR/2.5BA: office, private pool, pool house, outdoor dining, gas bbq, fire pit, stylish interiors, moments to beaches & wine country
Tucked away in the heart of Southolds wine country, this chic, modern retreat offers a resort-style escape that feels worlds away from the everyday. Thoughtfully designed for the discerning traveler, this property is more than just a vacation rental its an experience. From the moment guests arrive, theyre greeted with the refined sophistication of a designer home paired with the relaxed charm of the North Fork. With 4 bedrooms, 2.5 bathrooms, and a stand-alone guest house, this home comfortably accommodates up to seven guests, offering luxurious comfort and privacy for families, friends, or couples traveling together. Sun-drenched interiors, curated art, and open-concept indoor-outdoor living make this destination truly unforgettable.
Step into the expansive, fully fenced backyard and discover a personal paradise where every detail invites relaxation and connection. Lush landscaping creates a private oasis that wraps around the heated pool and built-in pool house, providing total seclusion. Guests can bask in the sun on chaise loungers atop the spacious sundeck or gather around the outdoor dining table for al fresco meals beneath the stars. The outdoor gas grill sets the stage for summer barbecues, while the paved firepit area promises cozy evenings with cocktails and conversation. Multiple seating areas, both covered and open-air, make it easy to entertain or retreat into solitude. Its a setting that evokes the atmosphere of a private resort, with all the comforts of home and plenty of free parking makes arriving and departing effortless.
Inside, the home welcomes guests with a warm, earthy elegance that combines modern lines with rustic, elevated touches. Natural light pours in through large windows, highlighting the homes stylish dcor and thoughtfully curated art. The main level flows seamlessly between the formal living room, dining room, and chefs kitchen a perfect layout for entertaining or relaxing. The living room is anchored by plush sofas and sweeping views of the pool and backyard, while the adjoining dining room features a striking table that seats eight comfortably. The kitchen is a dream for anyone who loves to cook or host, outfitted with top-of-the-line appliances, a spacious island, and all the tools and tableware needed for memorable meals. A wet bar on the main level adds to the homes social appeal, while a private office with a desk and sofa provides a quiet place to work or read. Additional amenities include central AC, high-speed WiFi, and a washer/dryer, making longer stays comfortable and convenient.
Each of the four bedrooms has been designed with serenity in mind, offering stylish, restful retreats outfitted with fresh linens and high-quality finishes. The primary suite, located on the second level, is a showstopper a vaulted ceiling and rustic wood paneling create an elevated yet cozy vibe. The adjacent spa-like bathroom features a luxurious walk-in shower and a freestanding soaking tub for the ultimate indulgence. Also on the second level is a guest room with a full bed, perfect for couples or solo travelers. A third bedroom, located on the main floor, offers a charming bunk bed setup ideal for children or close friends, with a stylish full bathroom just steps away. The fourth bedroom is housed in a beautifully designed guest cottage with wood-paneled walls and ceilings, a king-sized bed, a half bath, and its own kitchenette perfect for added privacy or a quiet escape.
Just minutes from the home, guests can explore the best of the North Fork. Southolds charming downtown is close by, where boutique shops, locally-owned restaurants, and art galleries provide plenty to see and do. Spend the day browsing unique antiques or sampling gourmet fare at one of the areas celebrated eateries. For wine lovers, the regions famed vineyards are just a short drive away, offering tastings, tours, and unforgettable views. Beaches dot the coastline within a few minutes reach, perfect for a morning walk, an afternoon swim, or a sunset picnic. Whether strolling through local farmers markets or enjoying fresh oysters by the water, guests will find that everything they need is nearby yet the peace and privacy of the home always feel a world apart.
Designed for travelers who appreciate style, space, and serenity, this Southold gem offers more than just a place to stay. Its a destination in its own right a refined, welcoming home where every detail is curated for connection, celebration, and escape.
This property has a max occupancy of 7
Bedrooms
Bedroom 1 - Bunk Bed: One Bunk Bed, First Floor/Main Floor, Air Conditioning, Standard Closet
Bedroom 2 - Guest: One Double/Full Bed, 2nd Floor, Air Conditioning, Standard Closet
Bedroom 3 - Primary: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Standard Closet
Bedroom 4 - Guest House: One Queen Bed, Guest House First Floor/Main Floor, Half Ensuite Bathroom, Standard Closet
Bathrooms
Bathroom 1 - Guest: Full Bath, First Floor/Main Floor, Shower
Bathroom 2 - Primary: Full Bath, 2nd Floor, Shower, Tub
Bathroom 3 - Powder: Half Bath, Guest House First Floor/Main Floor, Ensuite
Outdoors & Pool/Spas
Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture, Grill (Gas), Fire Pit (Wood), Private Pool (Outdoor)
Amenities
Bed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning, Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Coffee (Pot), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Private Entrance, Parking, Smoke Detector, Essentials
Location
Nearby Beaches:
Horton Lane Beach
Nearby Grocery Stores:
Wayside Market
Southold IGA
Nearby Restaurants and Bars:
Bedell Cellars
Pindar Vineyards
Duck Walk Vineyards
North Fork Table & Inn
La Cascada
Other Location Information:
Founders Landing Park
Horton Point Lighthouse Nautical Museum
Suitability: Not handicap accessible. Not suitable for unrelated guests.
Primary renter must be at least 28 years old.
Pet Policy: Pets are strictly prohibited at this property.
Utility Disclaimer:
Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $100.00 per night of the reservation.
Cleaning Disclaimer: One light cleaning per every seven days and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense.
Additional Guests: No additional guests beyond the max occupancy of this listing are permitted.
Events Policy: Events are prohibited unless express approval is provided.
Pool Disclaimer: Due to the climate of the northeastern U.S outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.
Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.
Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.
Note: All payments must be made prior to check-in
Payment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.
Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $5,000 of damage protection. Coverage details are provided in the booking agreement.
The guest experience for this property is managed by StayMarquis, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property.
Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Resort-Style Southold Retreat with Private Pool, Guest House, and Chic is located in Southold. Resort-Style Southold Retreat with Private Pool, Guest House, and Chic provides accommodation, featuring Security/Safety, Bedding/Linens, Ocean View, among other amenities. This House features Security/Safety, Bedding/Linens, Ocean View, to make your stay a comfortable one.

Resort-Style Southold Retreat with Private Pool, Guest House, and Chic has 4 Bedrooms , 2 Bathrooms, and max occupancy of 7 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Southold has interesting places to visit. If you want to learn more about the House in Southold, such as places to visit and things to do nearby, you can check below to learn more.