Southold Cottages

A calm lake with a forest in the background during sunset.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Southold cottages

1. North Fork Resort

Greenport

Lisa

P37,060 total

includes taxes & fees

Aug 18 - Aug 19

2. Hamptons Vacation Rental w/ Saltwater Pool

Hampton Bays

P105,163 total

includes taxes & fees

Aug 5 - Aug 6

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Kind and helpful staff. Didn't have a place to refill our water bottles but she gave us some complimentary water bottles. The room was comfortable and clean. There was a smell in the room and I couldn't tell if it was from cleaning supplies or the AC or what. I'm usually very sensitive to smells but thankfully whatever it was we got used to it and it didn't bother me. Appreciated the affordable price."

Water's Edge Resort & Spa

8/10 Good

"My husband and I chose this resort for a quiet and relaxing time away and the resort did not disappoint. The grounds are beautiful and meticulously maintained, including the beach and pool area. The room was spacious and very clean as was the whole resort. We got massages at the spa and it was amazing. The only small issue we had was at the restaurants. The food was delicious but they were short staffed on servers which made for delays on taking orders and receiving our food. We did find some great local restaurants though. We really enjoyed our stay and would definitely go back."

Sound View Greenport

10/10 Excellent

"My family and I recently stayed at the Sound View Hotel and had a wonderful experience all thanks to their front desk staffer named Adrianne. While our trip was off to a rough start regarding the initial room we were assigned, the moment I voiced my complaints to Adrianne she stepped in and went above and beyond to ensure we were more than happy with our room, and our overall stay at the hotel. If you want a wonderful getaway in Greenport, look no further!...Adrianne, thank you again for all that you did to make our trip so special. We are so grateful!"

Find out more about Southold