Compare best Airbnb in Southold, NY from 100+ providers!

Apartment to rent for 8 guests with an excellent rating of 100% based on 36 reviews. You will be located in Greenport.
Facilities and services: a wheelchair friendly access, a business center and a dish washer. This apartment in Greenport also has air conditioning!

Cliffside Resort Condominiums in Greenport offer direct beach access. Within 3 miles from major Greenport attractions, this aparthotel has very good user ratings and excellent location ratings.
The 550 square feet apartments have kitchenettes and multiple bathrooms, and furnished balconies. Amenities include a swimming pool, a garden, and barbecue grills. Guests can enjoy free WiFi and change of towels available on request.

Apartment to rent for 2 people with an excellent rating of 94% based on 55 reviews. Your accommodation will be based in Cutchogue.
Facilities and services: a washing machine, a kitchen and a fridge.

This 5-bedroom vacation home in Shelter Island Heights is a perfect getaway for families and groups. It's just a short walk from Crescent Beach and within easy reach of Shelter Island Country Club and Shell Beach. The house has received excellent user ratings, and it's easy to see why.
The house has 7 bathrooms, a fully equipped kitchen, and a private pool. It also has a fireplace, a washing machine, and barbecue grills. Guests can enjoy the outdoors on the patio, or relax in the air-conditioned living room. The house can accommodate up to 10 guests, and it's pet-friendly.

Cottage rental for up to 7 people with an excellent rating of 99% based on 54 reviews. Your accommodation will be located in Greenport.
Facilities and services: a fridge, a coffee place and free parking. Take advantage of the garden in this accommodation!

This renovated wine country home is located in New Suffolk, within walking or biking distance of the beach and waterfront. It has excellent user, location, and cleanliness ratings.
The apartment has a spacious layout with beautiful wood floors and sleeps 8 comfortably. It boasts a floor area of 1700 square feet and has 2 bathrooms. Amenities include a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a garden, a spa, parking, and games and recreational amenities such as bikes and bocce.

This waterfront cottage in Southold offers a unique retreat in the heart of wine country, just a 5-minute walk from the sandy beach of Long Island Sound. With excellent user ratings, this recently remodeled cottage provides a comfortable and convenient stay for up to 5 guests in its 1500 square feet of space, featuring 3 bedrooms, 1 bathroom, and a full-sized bedroom loft.
The cottage boasts modern amenities such as a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as access to a range of outdoor activities including kayaking, snorkeling, cycling, and horse riding.

Vacation rental listing for up to 6 guests with an excellent rating of 99% based on 401 reviews. This accommodation is based in Greenport.
Services and facilities: an iron, a washing machine and a child space. Take advantage of the terrace in this apartment in Greenport.

Apartment for 8 guests with an excellent rating of 98% based on 175 reviews. You will be based in Greenport.
Services and facilities: air conditioning, a washing machine and an iron. This is a pet-friendly apartment!

Vacation rental listing for 6 guests with an excellent rating of 98% based on 399 reviews. You will be in Greenport.
Services and facilities: air conditioning, a kitchen and a garden. This apartment in Greenport is ideal for families.

House rental for 8 guests with an excellent rating of 98% based on 68 reviews. You will be based in Greenport.
Services and facilities: a barbecue, a garden and a terrace.

House with an excellent rating of 96% based on 5 reviews. This accommodation is located in Greenport.
Services and facilities include free parking, an iron and a fitness center. This is a pet-friendly house!

Apartment rental from $606 for 10 guests with an excellent rating of 85% based on 4 reviews. This accommodation is based in Peconic.
Facilities and services include air conditioning, a kitchen and a jacuzzi. This apartment also has a garden!

Apartment for up to 2 guests. This accommodation is located in Greenport.
Facilities and services include a fridge, air conditioning and a fitness center. Take a dip in the pool of this apartment in Greenport!

Vacation rental listing for up to 6 guests. This accommodation is located in Greenport.
Services and facilities: a swimming pool, air conditioning and a barbecue. Enjoy free parking with this accommodation in Greenport!

Accommodation for up to 4 people with an excellent rating of 98% based on 46 reviews. This accommodation is located in Southold.
Facilities and services include a dish washer, a fridge and air conditioning. Take advantage of the gym in this apartment in Southold.

Apartment rental listing for 4 people with an excellent rating of 100% based on 23 reviews. You will stay in Greenport.
Services and facilities include free parking, a washing machine and a fridge. Take advantage of the air conditioning in this apartment!

Vacation rental listing for up to 6 people with an excellent rating of 100% based on 36 reviews. Your accommodation will be located in Greenport.
Services and facilities: a fridge, a terrace and a dish washer. This house in Greenport also has a garden!

The Chequit Hotel is situated in the tranquil surroundings of Shelter Island Heights, within easy reach of the Shelter Island Country Club and the historic Sylvester Manor.
The hotel offers 35 cozy guestrooms with blackout drapes for privacy, as well as a range of amenities including an on-site restaurant, coffee shop, free Wi-Fi and self-parking.

Farm rental from $958 per night for 6 people. You will stay in Southold.
Facilities and services: a barbecue, a garden and a dish washer.

Accommodation for 10 people with an excellent rating of 97% based on 7 reviews. You will be in Southold.
Services and facilities: a barbecue, a kitchen and a fridge. Take advantage of the terrace in this house!

Cottage for up to 6 guests with an excellent rating of 100% based on 4 reviews. Your accommodation will be located in Cutchogue.
Facilities and services: free parking, a kitchen and a freeze. You can bring your favorite pets this accommodation!