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Our top choices for Southold apartments

"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"

CA $359 total

includes taxes & fees

Aug 31 - Sep 1

"The week went by fast and we enjoyed our time there. Beautiful home and landscaping to enjoy as well as great location to Hamptons."

CA $405 total

includes taxes & fees

Sep 21 - Sep 22

"Very much enjoyed our stay!"

CA $494 total

includes taxes & fees

Sep 1 - Sep 2

"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "

CA $261 total

includes taxes & fees

Sep 4 - Sep 5

"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "

CA $239 total

includes taxes & fees

Sep 3 - Sep 4

"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"

CA $274 total

includes taxes & fees

Sep 3 - Sep 4

"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "

CA $257 total

includes taxes & fees

Sep 3 - Sep 4

"Very nice, clean and convienent place to stay. Very comfortable."

"The accommodations were excellent and we enjoyed our stay "

"Great stay in Greenport. The hosts, accommodations are location are wonderful. Look forward to another visit."

"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."

CA $816 total

includes taxes & fees

Aug 29 - Aug 30

"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."

CA $347 total

includes taxes & fees

Sep 3 - Sep 4

"The location is perfect, just a few houses from the beach. The unit has a great view, very clean and new. The owners/managers were very prompt and communicative. I was VERY hesitant to book a place without reviews- but this was an excellent choice. The beach is clean and private, people are friendly. I will happily stay again!"

CA $317 total

includes taxes & fees

Sep 3 - Sep 4