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Browse Select Southold Holiday Homes

Our top choices for Southold holiday homes

"Great place! Great communication with property owner!"

includes taxes & fees

21 Aug - 22 Aug

"Loved our stay and will be back"

"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "

includes taxes & fees

1 Sept - 2 Sept

"We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. "

"Perfect location."

"Amazing property! Had all the things we needed "

"The is great!!! Very convenient location and plenty to do."

Beach nearby, sun-loungers, beach towels

"Very clean well kept property near beach - host very welcoming and receptive. Enjoyed our stay!"

"Nice property, conveniently located, great host!"

"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "

"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."

"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"

includes taxes & fees

14 Sept - 15 Sept

"Perfect property to hangout and stay entertained for hours"

"Great location, clean, easy checkin, slept 7 comfortably"

"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."

"Great job "

includes taxes & fees

28 Aug - 29 Aug

"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...

"This home fit everyone perfectly. The great room was a stunner and the bay views awesome! "

"This place is an absolute gem. Four big bedrooms, a brand new kitchen and washer/dryer, lovely renovated interior, and huge fluffy towels in excess! A huge backyard with plenty of toys for little ones and a big patio table and chairs to enjoy amazing grilled dinners from the new gas BBQ grill was a huge plus. Also lots of beach chairs, beach towels, umbrella available for use! The owner was extremely communicative, thoughtful, and an excellent host. This house is on a QUIET street in busy Sag...