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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 4 Houseboats in Southold with updated reviews, rates, and availability.

Peconic River Boatel
Outdoor dining

Peconic River Boatel

10.0 out of 10, Exceptional, (10)
"My wife and I just finished our wedding weekend in Riverhead, I was lucky enough to stay at the Boatel the night before my wedding, and it was the perfect way to kick off such a special occasion. Katy was incredibly responsive and provided great information about the area. She even surprised us with a bottle of champagne to celebrate! The surfboard and nautical theme creates a modern, comforting aesthetic that's perfect for a waterfront stay. Perfect for everyone. It's also within walking...
Peconic River Boatel
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Dining

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (9)
"Super cozy stay with the aquarium close by. Clean and very unique. Had a great time with my girlfriend definitely recommend "
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Spend Your Summer on a Prestige 500 55ft. Yacht in Beautiful Sag Harbor
Room

Spend Your Summer on a Prestige 500 55ft. Yacht in Beautiful Sag Harbor

Spend Your Summer on a Prestige 500 55ft. Yacht in Beautiful Sag Harbor
Gorgeous Vintage Yacht in Wine Country NY
Exterior

Gorgeous Vintage Yacht in Wine Country NY

Gorgeous Vintage Yacht in Wine Country NY
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Southold

Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (273)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great "
The price is AED 484
AED 632 total
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort
Stunning Hampton Holiday Family Fantasy for your Team
Safety gates, privet-enclosed, private pool, spa, and pool house.

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team
10 Bedroom Hampton House with a regulation size Pickleball
Pool

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.