Southold

Boutique Hotels in Southold

Enter your dates to find boutique hotels in Southold that offer unique style and charm.

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Top Boutique Hotels Southold

Discover the best boutique hotels in Southold, celebrated for their unique style and personality.
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“Paradise Found” - Walk to Private Beach & in-Ground Pool!
“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!
23
Hotels in Southold
Featured facilities: Pool
Outstanding
5 reviews
10.0/10
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Lovely Cottage in the Heart of Long Island Wine country
Lovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine country
21
Hotels in Southold
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.
Outstanding
18 reviews
9.8/10
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Water Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large Deck
Water Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large Deck
37
Hotels in Southold
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.
Outstanding
5 reviews
9.8/10
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Southold
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Country BEACH home!
Country BEACH home!Country BEACH home!Country BEACH home!Country BEACH home!Country BEACH home!Country BEACH home!
27
Hotels in Southold
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.
Outstanding
9.8/10
Check Availability
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