Best Southold Hotels

This property is a newly renovated historical Victorian House built in the late 1800's. Each room is furnished with hand-selected unique antiques to immerse you into the 19th century. Staying here feels like experiencing the past, but with all the benefits of modern life!Excellent location for Bachellorretes, Weddings, Family gatherings. The house has plenty of space for up to 14 people to sleep comfortably and large dining tables to fit a family.Fully loaded with a pantry and full sized kitchen. A patio is available to you if you choose to do outdoor BBQ. There is grass space for your children to run around as well!This property is in the heart of the NORTHFORK wine country.The nearby locations of this area are outstanding!- You can walk to plenty of wineries and vineyards in just minutes.- The Greenport Harbor Brewery is just a 5 minute walk.- You can travel to this location with the HAMPTON JITNEY since the bus station is also just a short walk.If you have a car available to you then: - You can drive in 5 minutes to nice beaches.- You can drive to Southold & Greenport town and explore the plethora of options available to you, including playgrounds, restaurants, and stores to shop in.Come by and enjoy fishing, boating, hiking, golfing, tennis, bird watching and anything else there is to offer!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Adults only.About customRules:Owner sometimes lives in own quarters. Uses a separate discreet entrance. Will not interfere with guests..In case of small groups, not all rooms may be available. Please note , rates are for 6 people additional adults are subject to additional fees.,No Large Gatherings NO PROMS or PARTIES/EVENTS No additional guests allowed beyond what was stated in booking..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.UNLESS DISCUSSED WITH OWNER.

Take it easy at this brand new unique retreat. Walking to distance to the beach and winery. Less than a 2 minute drive to the famed Halyard Restaurant. 5 minutes from countless additional wineries and more restaurants and shops. Relax on the oversized back patio or in front of the firepit. Enjoy all the North Fork has to offer including world famous wines and food. Don't forget to save room for the pies! PICTURES OF FULL SIZED BUNK BEDS COMING SHORTLY! Please message me with any questionsAbout pets:Pets allowed: limit 2 total.About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.About checkIn:Check in after 1:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Take in the extensive views from this lovely Goose Creek Front waterfront vacation home, with private deck and beach. Top rated Southold beach destination just across the street and close to the Southold Yacht Club on the bay. Explore the North Fork from a different vantage point; rent a boat from Strong's Marina dock it at the house, or take to the lagoon on our one of two kayaks. Enjoy the fire pit with family/friends on our private beach.The main level bedrooms, on second floor, feature a King ensuite master bedroom and the second bedroom contains a King size bed. Also, there are two full bathrooms on this floor. The main living area offers a modern kitchen, living room, and dining with 180 degrees views of the water (via an outside balcony). Take advantage of the flow onto the shaded deck with picture perfect views. Entertaining spaces inside and out!The first floor offers two bedrooms, one with a bunk bed of 3 full-size beds and the second room with a Queen size bed, as well. Also, the is a full bathroom, living room, and updated bar area.The attic offers 2 queen size beds. It is equipped with a TV, an additional AC unit and a sun-window.About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.Smoking is permitted in outside areas..About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

This charming Southold village house sits on a half acre with a back deck overlooking a sweeping backyard. Newly furnished and freshly painted, it is centrally located to wineries, bay and sound beaches and is a short walk to shops. Enjoy the sunset on the deck or in the hammock and maybe get a glimpse of a deer family that often walk by. Come enjoy all that the wonderful North Fork has to offer! Taxes: as of 2023, Suffolk County is requiring us to charge 5.5% tax per booking, please note this is in addition to State of New York sales tax of 8.625%, hence the total taxes due are bundled together for a total of 14.125%....About pets:No pets allowed.No.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Yes.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.No.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.No.

Steps from Peconic Bay and Cedar beach. Stay in our Southold home in the heart of North Fork and enjoy the best the North Fork has to offer! The location is ideal with Cedar beach/Peconic Bay just a block away and all the beach essentials, kayaks included, with your stay. Our 3 bedroom, 1.5 bathroom home is surrounded by award winning vineyards & farm stands. Southold town center is an 8min ride where you'll find restaurants, local shops, and a grocery store. For more restaurants, shopping or the ferry to Shelter Island/ South Fork, Greenport village is just a 12min drive away.We have 2 single kayaks (with wheels) for use. You can launch directly into the Peconic Bay off of Cedar Beach, (short walk from the house). There are also beach chairs, beach towels, and a folding wagon to carry equipment to the beach. Sleeps 6 people comfortably. 2 bedrooms with 1 queen bed in each and a 3rd bedroom with two twin beds. If you have 7 people, there is also a pull out queen sofa for use with sheets and pillows in the living room. If you have a little one, we have a crib with sheets and a highchair available for use as well. Additionally there is one full bath, one half bath and a enclosed outdoor shower. There are window A/Cs in the dining room, master bedroom, and guest room. The children's room has a ceiling fan and a floor fan.House is fully equipped. Includes washer/dryer, fully stocked kitchen, sheets, towels, shampoo, soap etc. It has Wi-Fi and even a desk with a high definition monitor if you need a place to work. There is also YouTube TV (40+) channels. As mentioned, beach equipment is included (towels, beach umbrella, chairs, etc). There is also a record player and selection of records for your use. There is a bright & beautiful dining area with a door that leads to an outdoor patio. The patio has a full sized table and 6 chairs in case you prefer to eat in the fresh air. There are folding chairs for extra guests. There is a grill & fire pit for use as well. Take a glass of wine out to the back yard or a cup of coffee down to the water to overlook the sound. Use the grill to cook up fresh fish from Southold Fish Market or just sit by the fire-pit to chat with friends & family. We also have a handful of yard games for your enjoyment!We look forward to hosting you and your family for a well deserved relaxing & fun vacation on the Fork! ** indoor fireplace is not in working orderAbout pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Must use yellow trash bags provided for trash per town rules.Dishes should be washed upon checkout.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 24.About events:No events allowed.

Escape to paradise with this stunning north fork home, where relaxation and adventure meet! A quick walk to the beach, this beautifully designed 3-bedroom, 2-bathroom retreat is the ultimate getaway for families or groups seeking a beachside escape with updated amenities and plenty of space. Serene backyard includes large outdoor dining, fire pit and pool. This property offers a combination of tranquility and excitement. Get ready to explore all of what Southold has to offer!Key Features:Beach Location: 5 minute walk to beach with private access. Wagon, beach chairs, umbrellas, coolers, kayaks & lifejackets available. Updated Kitchen & Living Space: Living room features wood burning fire h place, large screened in porch with dining, cozy TV room with pull-out queen couch. Semi open floor plan with great entertaining flow. Gourmet Kitchen: Fully equipped with high-end appliances, sleek countertops, and all the cookware you'll need to prepare gourmet meals. Large island with seating for 8. Gas grill with propane. Spacious Bedrooms: Master suite hosts a king-sized bed, with en-suite bathroom. Additional bedrooms sleep 2 adults, each. Entertainment: High-speed Wi-Fi, TVs in main living areas. Bikes for adults and children. Outdoor Oasis: The oversized deck is perfect for dining al fresco or lounging with friends and family by large pool. The property also includes a fire pit for those cozy evening gatherings.Ideal Location: Located in a quiet, upscale neighborhood, perfect for those who want to escape the hustle and bustle while being close to everything the north fork has to offer. Local wineries, breweries, restaurants, shopping, and attractions. Enjoy the best of both worlds – peaceful beach days and easy access to nearby activities.Book Your Stay Today!This beach house is the perfect place to unwind and create lasting memories. Don’t miss out on your chance to stay at this North Fork dream getaway! Here is a link for a video walkthrough : https://youtu.be/nQPoGqOaQ3MAbout pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:Events allowed: family gatherings and birthday parties.Maximum event attendees: 15.

Peaceful pondfront cottage with two bedrooms , 1 1/2 baths, pull out couch in Living room can sleep two more , and lovely screened in front porch to enjoy the beautiful pond view-watch ospreys fly over, or enjoy the pond by using kayaks, paddle boats or canoe that comes with the rental. 10 minute walk to beautiful sound beach around the corner-minutes to wineries, Southold village, and Greenport. About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.

In the picturesque seaside village of Greenport, this ocean-view three-bedroom retreat provides a peaceful and refreshing getaway. As you step inside, you'll be greeted by a fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the necessary appliances to satisfy your culinary cravings. Unwind in the cozy living room, where you can enjoy the smart TV with satellite/cable channels or simply gaze out at the breathtaking ocean views from the balcony. Indulge in the convenience of a washing machine and dryer, ensuring you can pack light and enjoy your stay to the fullest. Explore the nearby Kontokosta Winery, just a 3-minute drive away, or venture to the picturesque 67 Steps Beach, only a 4-minute drive from your doorstep. For a more extensive wine tasting experience, Raphael Winery is just a 9-minute drive away.Relax on the beach towels, soak up the sun, and enjoy the outdoor furniture and fire pit, creating the perfect setting for memorable gatherings. With air conditioning, linens, and essential toiletries provided, you can truly immerse yourself in the comfort and tranquility of this beachfront haven.About pets:Pets allowed: dogs (limit 1 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Perfection!!Amazing, centrally 🌊 located getaway in the middle of EVERYTHING that the North🍷Fork has to offer. BEAUTIFULLY designed with architectural details throughout. Open floor plan, INDOOR SHUFFLEBOARD, large 🔥 fireplace. Huge Chefs 👩‍🍳 kitchen is AMAZING!! Minutes to Wine 🍷Country, farms, shoppes, and restaurants. So much to do or just relax 💤 and enjoy the beautiful tranquilpatio, new Weber BBQ, 🍗 and landscaped 🌹 yard. Beach gear, PADDLE BOARD, bicycles, 10 beach chairs, 4 🍺 coolers, 4 beach 🏖️ umbrellas, beach toys/games for you. About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.

When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella Vineyards. This hotel is 2.6 mi (4.2 km) from Custer Institute and Observatory and 3 mi (4.8 km) from Railroad Museum of Long Island. Make use of convenient amenities such as concierge services, shopping on site, and wedding services. Additional features at this hotel include a communal living room, a picnic area, and a ballroom. Enjoy a meal at the restaurant or snacks in the hotel's coffee shop/cafe. Wrap up your day with a drink at the bar/lounge. Featured amenities include a business center, luggage storage, and a safe deposit box at the front desk. Make yourself at home in one of the 20 individually decorated guestrooms, featuring espresso makers and flat-screen televisions. Your bed comes with down comforters and premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access is available to keep you connected. Bathrooms feature showers with rainfall showerheads and hair dryers.