- Entire Place
- Listings where you have the whole place to yourself.
- Private Room
- Listings where you have your own room but share some common spaces.
- Shared Room
- Listings where you'll share your room or your room may be a common space.
- Room Type
- Social Connections
- Employee Host
- Instant Book
- Property Type
- Host Language
1000+ Rentals · Southold
1000+ Rentals · Southold
Welcome to my incredibly cozy Southold cottage. Located steps to the Peconic Bay, village of Southold and a short lovely bike ride to the beach. This 2 bedroom 1 bathroom home has all you need for a memorable vacation. Learn More
Located off a private gravel road overlooking the Peconic Bay, tucked away on 1.5 acres providing ultimate privacy. The large outdoor screened furnished porch provides the ultimate relaxation while enjoying the sunset. The spacious furnished backyard is ideal for grilling, playing sports, lounging on the hammock or listening to the birds. Guests have access to 2 bicycles, charcoal grill, fully stocked kitchen, fresh linens, cable TV, wireless internet, CD/Ipod player and books. Washer / D...
Clean, bright 3 bd/1 bth. 5 minutes to vineyards and the historic seaport town of Greenport. Walk to Kenny's Beach-- we have beach chairs, towels and a wagon to haul your cooler. Bicycles included! Learn More
This is our pretty three-bedroom ranch-style cottage, fully equipped, one block from Kenney's Beach; spend the day in the sand or visit the vineyards, Greenport, Shelter Island--this house is central to everything. A short walk to the beach, bike or drive to vineyards. Bike into Greenport and take the ferry to Shelter Island! Newly furnished and freshly painted, this home is immaculate. Wifi with booster, landline telephone, television with DVD player, washer and dryer, dishwasher, mi...
Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse has complete privacy. Hammocks, outdoor fireplace, bikes, and kayak available. A bird lovers' paradise. Learn More
Idyllic writers retreat- quiet, peaceful, no car needed. Our renovated farmhouse is nestled in the woods off the Main Rd, so you get the country feeling and a lot of privacy, but can walk to restaurants, shops, grocery store. Bike to wineries and beach (Long Island Sound or Peconic Bay). From NYC you can take an express bus or train and walk to the house! After a brisk walk or bike ride sit in front of the roaring fireplace. Talk to us about a monthly or seasonal winter rental at a reduce...
In the heart of Long Island wine country and beautiful beaches we have an Historic Inn built in the 1830's that has been carefully renovated to retain its old time feel Each cottage/unit has 2 bedrooms each with a double bed and patio. Come enjoy! Learn More
Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of town In the heart of the North Fork Wine Country and beautiful beaches. We have a 1840's home with a furnished attached cottage available for weekend's, week or month rental. Cottage has small eat in kitchen, bath, living room and 2 bedrooms. One bedroom has a queen size bed and the other a full size bed. Separate entrance wi...
Located just across a small street from a private beach in beautiful Southold, on the northeastern end of Long Island, NY, this wine country condo can be found on a huge private sandy beach. It is on the second floor of a condo complex which includes 42 units. Visitors from NYC, PA, Connecticut and Massachusetts can reach us in about 2 to 3 hours. The condo has 3 rooms and accommodates 6 people comfortably. The first room has a full size bed with table and chairs, Directv cable television,...
Our studio waterfront escape provides the perfect sunny setting for a weekend retreat all year round or a lingering vacation. Nestled on a lake like bay setting with beautiful lawn, yet with access to long island sound a block away. Learn More
Enjoy sun year round and beautiful flowers in seaon while you are surrounded by nature in our waterfront private studio cottage with new full bathroom, kitchen and flooring and cathedral ceilings. Cozy furnishings and fully stocked kitchen. Original mosaic mirrors and local artwork on display. Outdoor area with beautiful view over pristine Ashamamoque Pond to private preserve. Enjoy the idyllic setting with sightings of osprey, egrets and swans. Fishing in the bay and access to private...
2 private upstairs bedrooms with microwave, fridge and shared bathroom. 4 beds. Views, A/C, heating and Internet with TV access. 5 min. walk to beach. Quiet street. Deck/bbq access. 10 min. to wineries and Greenport. 20 min. to/from Orient Ferry. Learn More
Exclusive use of the upstairs area--2 bedrooms, with 2 beds in each. Private. Views front and back. Weekends April thru November are 2 night minimum stay. We will consider single night stays depending on availability. Deck with BBQ, garden, living room and kitchen. Hosts will be present on property during your stay. Join us for coffee and a chat or find a private place to enjoy the morning. We have two Golden Retrievers and a cat. Quiet, tree lined streets and it's walking distance to a...
Spacious 4 bedroom, 3 bathroom home in the heart of Wine Country on Long Island’s North Fork. Just steps to bay beach. Short drive to Southold & Greenport. All seasons incl Winter Wine wknd, girls' getaway or bachelorette & wedding parties. Learn More
LOCATION: •Southold, North Fork of Long Island. •Antiquing, fishing, kayaking, bike riding, golfing or just lounging on the beach. •Just minutes from Greenport Village •Short drive to Tanger Outlets and Splish Splash Water Park DETAILS: FIRST FLOOR •Bedroom 1 – Queen-sized bed with en-suite Bathroom 1 with tub, also sitting room with skylight •Bedroom 2 – Two twin beds, bay window. •Bathroom 2 – Full bathroom ...
Ground floor master suite with private bath and separate entrance off a beautiful patio and large country backyard. Amenities such as WiFi, flat screen TV, A/C, Jacuzzi and use of private pool make this an ideal get-away spot! Learn More
Guests have access to nearby bay beaches, minutes from quaint towns and wineries galore. Interaction will vary- hosts will not always be available depending on schedule. The neighborhood is very quiet surrounded by several acres of nature preserves- close to town and beautiful bay beaches. A car is necessary, although beach is within walking distance. We have three wonderful cats.
What I love most about my house is the closeness of nature around you. In the morning you are greeted by the sounds of all different kinds of birds and looking out of the kitchen windows toward the lake you will often see deer and other wildlife. Learn More
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Barbecue and dine in the spacious backyard with a sunset view of the lake. Stargaze with no interfering city street lights. House has two bedrooms and a queen size sofa bed a...
Our peaceful, cozy home, built in 1910 with modern updates, is centrally located near vineyards, beaches and Southold town. Enjoy multiple patios, picturesque yard, large kitchen and family-friendly amenities. 1 mile from Goose Creek beach. Learn More
Sunny, charming 3 BR home with cozy character, ideal for entertaining and families. Hardwood floors, bright rooms, plentiful outdoor space. Bike ride to beach (1 mile), Southold town (1 mile) and creek access (1/2 mile). Less than 5 mins from some of North Fork's finest wineries and farms. Upstairs are 3 bedrooms, with 4 beds and room to sleep 7 comfortably, and full bath with glass block walk-in shower and vintage pedestal bathtub. Spacious downstairs with 2 sun-drenched living areas (inc...
Well laid out beach bungalow just a few yards from the water, and a 5 min walk to the town beach. Large yard, spacious living room, large master bedroom (14x18) with two smaller bedrooms. Very functional kitchen, screened in porch and second full bth Learn More
Don't miss out on this cozy bright renovated waterfront North Fork home, surrounded by nature. Spend the off season with us. Relax by the fireplace and enjoy the privacy. And book now for summer. Filling up fast! Learn More
Enjoy sunshine year round and abundant flowers in season. Join us at our three bedroom one bath renovated house. Private waterfront. Stone fireplace and central AC. Beautiful hardwood floors and custom light fixtures. Open and airy. Fully stocked kitchen with 5 burner stove, stainless steel appliances and custom built island. Large deck and great outdoor furniture. Nice selection of book and games. Access to both dock and pond and LI Sound, block away. Semi private Golf Course clo...
Our comfortable house on the North Fork of Long Island has three bedrooms and 2 (website hidden) is located in a quiet neighborhood in Southold with a private beach looking out to Shelter Island.We have a water view from the deck.Has central air conditioning. Learn More
The home is very cozy and tranquil, in a great location. The home is open concept with a great room, including living room, kitchen and dining room. There is a cathedral ceiling in the great room. Guests will have access to bicycles, a kayak, wagon, fishing equipment, towels, linens, kitchen utensils, barbecue, wifi, 3 flat screen TV's, I pod/CD dock, a guest handbook and much more. The owner will greet the guest upon arrival. The neighborhood is very quiet and relaxed, with the historic...
Lovely 3 bedroom 2 bath beach house on private road.Creek views a short walk to long sand bay beach. Perfect getaway for couples, families on 1/2 acre deer fenced property. Near bay and sound beaches, wineries, kayaking,hiking,bicycling,farm stands Learn More
A short walk to beach. we have kayaks and bikes if you want. Property entirely deer fenced, very safe for children to play outside. Kitchen fully equipped for cooking. Grill by patio. Outside shower hot and cold water Great restaurants, near all wineries, many beaches on bay and Long Island sound. Guest beach car pass extra cost, if wanted. If walking no pass necessary for our bay beach. Sorry none, we will give guests local contact information who will meet guests, show house and give ke...
1 month $8300. 1 week $2500. $500/night. Private pool area, cathedral ceilings, indoor/outdoor living on 3/4 of an acre. Less than a mile to village and beaches. Charming One Woman winery down the quiet street. Learn More
Please inquire for weekly or monthly rental. Spacious, private, quiet, has a pool and huge deck, and is 1 mile from the Bay and the Sound. This is a three bedroom, 3/1/2 bath with cathedral ceilings on the most beautiful street in Southold. 1 mile from Southold village and 3 miles from Greenport village. Jitney/LIRR stops in Southold. Large kitchen with island. Counter flows into great room, pool area and upper deck off kitchen. Lots of windows and french doors. Bottom floor separate...
Lovely 3 bedroom house across street from water in Southold, Long Island. Enjoy the tranquility of the country and a view of Hashamomock (Arshamonaque) Pond - an inlet of the Bay. Located on a peaceful dead end street, a short walk (2 houses down and across street) from the public boat access of Hashamomock Pond - great swimming, wildlife viewing, fishing, and boating. We are walking distance from Farmer Joe's Farm Stand, a 5 minute drive from Southold's Sound Beach, and less than 10 minutes ...
Beautiful home on gorgeous tree-lined street on the North Fork of Long Island. Near to Greenport, Mattituck, Cutchogue, Orient, vineyards, beaches, farm stands and golf courses, although sparkling pool and sprawling front porch may keep you at home! Learn More
A very spacious house, 4 bedrooms, 4 bathrooms, dining room, sitting room, large kitchen, large and gracious front porch, swimming pool, large family room with ceiling fans, two fireplaces. Bedrooms on second floor are air conditioned. Very simply and tastefully furnished. Walking distance to charming town of Southold, 5 miles to Greenport with its quirky shops, movie theatre and carousel for kids, many farm stands nearby, famous Long Island vineyards, much more. We are available at all t...
Book without waiting for your reservation to be accepted