Find & Book the Best Hotels in Town of Southold Town for 2025

Top Cities in Town of Southold Town

Beautiful spot on the #longisland sound surfing

Compare 572 hotels in Town of Southold Town with room rates, reviews, and availability. Most hotels are fully refundable.

Seasonal outdoor pool, pool umbrellas, sun loungers

"We had an overall great stay and will be back. Especially loved nights out on the beach!"

₩740,800 total

includes taxes & fees

Jul 20 - Jul 21

"The best thing about this hotel is the location. "

₩454,841 total

includes taxes & fees

Jul 1 - Jul 2

"We love this hotel "

"Wonderful location and hotel "

"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "

₩407,259 total

includes taxes & fees

Jul 6 - Jul 7

Garden Suite King | 1 bedroom, premium bedding, down comforters, individually decorated

"Great stay! Room was very spacious and clean! Loved the outdoor space with the picnic tables and food truck. Such a great weekend, staff was very kind. "

₩483,458 total

includes taxes & fees

Jun 29 - Jun 30

"This hotel is clean, trendy and very welcoming "

₩647,924 total

includes taxes & fees

Jun 29 - Jun 30

Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas

"A weekend celebration. We love the hospitality, location and amenities of this luxurious place. "

₩1,201,266 total

includes taxes & fees

Jul 7 - Jul 8

"Beautiful hotel , attentive staff and close to everything. Great food and cocktails "

₩457,197 total

includes taxes & fees

Jun 30 - Jul 1

"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "

"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "

"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"

"Lovely B&B run by a lovely couple"

"Two mid age couples just had a good and relaxing time with great hospitality. "

"Mark and Mona were great hosts. The house and grounds were beautiful. Southold is a great town to explore and the house is close to the beach and the town. We loved the use of the bicycles which made our trip much more fun. We could ride to the beach, the town, and the wineries. Mona even pumped my bike tires before we went to explore. Thanks for a great time and we hope to be back again next year !"

"This was the perfect, in town place to stay for the two of us. Located on a quiet street of well-maintained homes, and with parking right outside, it was a short 1-1/2 block walk to all the shops, restaurants, ferry, docks, etc. The apt is small, but clean and tidy, sun-filled and air-conditioned. We loved staying here and will again in the future."

Apartment (2 Bedrooms) | Front of property

"extra clean brand new rooms. bathroom door did lock by itself and the small hole on the plate outside did unlock it when depressed otherwise perfect. we had 2 under 3 kids and the way it was set up was safe and fun"