Southold Vacation Homes

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

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Our top choices for Southold holiday homes

Adorable Cottage, 5 min walk to water & town

Westbrook Center

Donovan V.

HK$3,749 total

includes taxes & fees

28 Jun - 29 Jun

Rogers Lake House (87) · CT College+Beach+USCGA

Old Lyme

Cheryl H.

HK$3,753 total

includes taxes & fees

28 Jun - 29 Jun

Black Swan Beachfront Home with Jacuzzi year round

Hampton Bays

Ana B.

HK$10,435 total

includes taxes & fees

30 Jun - 1 Jul

The Bay Cottage · Rocky Neck Park, Beach & Niantic

East Lyme

Sarah G.

HK$3,822 total

includes taxes & fees

29 Jun - 30 Jun

BlackBerry Private home with jacuzzi yearlong

East Hampton

Suzanne R.

HK$7,971 total

includes taxes & fees

28 Jun - 29 Jun

Villa Luz Family Home w/ heated pool & jacuzzi

Hampon Bays

Annie B.

HK$13,163 total

includes taxes & fees

30 Jun - 1 Jul

American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

HK$3,118 total

includes taxes & fees

29 Jun - 30 Jun

NEW Coastal Cottage 2 Miles to Beach + Lake Access

Clinton

HK$2,468 total

includes taxes & fees

30 Jun - 1 Jul

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Top Southold Hotel Reviews

The Hampton Maid

10/10 Excellent

"Our stay at the Hampton maid was absolute perfection from start to finish. The representative at the front desk, went above and beyond to make us feel welcome, ensuring a seamless check-in and offering incredible personalized recommendations for the area. When we opened the door to our room, we could not believe the features that were offered to us for our stay. Refrigerator was filled with cold beverages for purchase also snacks, and other amenities located on the table near the window. The bathroom products they offered were top notch with incredible fragrances. The linens were crisp and clean, and the comforter was amazing. The pool was clean and inviting while the lounge chairs were comfortable, and they also offered pool towels that were extremely large and thirsty. Our first night we dined in the hotel restaurant and took advantage of the happy hour menu, which was extensive and reasonably priced . The presentation of each item that we ordered was flavorful and delicious. The bartender had extensive knowledge of the wine list and suggestions were also offered by the head chef. Upon the completion of our dinner we return to our room and sat outside on our deck. It felt like we were sitting in a mountain like setting as we enjoyed the serenity of the surroundings. We could not have picked a better spot and amore enjoyable two night retreat. This place is worth every penny"

North Fork Resort

10/10 Excellent

"We loved our stay at the North Fork Resort. We would definitely recommend. Family & pet friendly to the max! Any hiccups we had with our stay were resolved without hesitation or annoyance by the staff. They were incredibly accommodating. The pool area was spacious and clean but the pool itself was a little chilly. It's a nice property to walk around with your family and/or pets. They have at least two doggy poop bag stations (that I noticed) located around the property in case you run out. They've seem to think of almost everything you could need. The only thing I could think of that would make the space better was a large garbage can outside of all the cabins. I noticed some had them but ours didn't. An overall wonderful experience!"

The Pridwin Hotel

8/10 Good

"We were at the Pridwin because of a family wedding on Shelter Island. What an absolutely beautiful hotel! The location is fabulous, right across from the bay and the hotel is designed to really take advantage of the views. Our compliments and thanks to the outstanding staff, they were so warm and helpful! I would go back again in a heartbeat."

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