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Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

Compare 1861 Vacation Homes in Southold with updated reviews, rates, and availability.

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
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Terrace/patio

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Waterfront House with picture-perfect views from all 3 levels.
Interior

Waterfront House with picture-perfect views from all 3 levels.

9.8 out of 10, Exceptional, (82)
"We had an amazing weekend celebrating my husbands birthday. The house was perfect. The view was priceless. The beach was amazing. It was the first time we were able to travel with our dog, and he had the best time at the beach. We will be returning for another vacation for sure. "
Waterfront House with picture-perfect views from all 3 levels.
Stunning New Designer Renovation
Terrace/patio

Stunning New Designer Renovation

9.4 out of 10, Exceptional, (21)
"We had a wonderful stay at this home! The yard is the most spectacular thing ever- pictures don't do it justice! And the location is wonderful. Great for our growing family :)"
Stunning New Designer Renovation
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (176)
"We were a large group of friends who all spent the weekend here. We had plenty of space (everyone had their own bed) and tons of bathrooms which makes it great for a large group of adults. We also enjoyed that it was walkable to town and in a very central location to many activities within the area. Mark was extremely responsive and helpful before and during our visit, and we already are looking forward to being able to coming back in the future! "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (129)
"We came to enjoy a nice relaxing weekend with friends and were overwhelmed with how amazing the beach house was! Completely set in the perfect spot! We loved the space and all the games! Thank you for creating such a fun home! We will be back "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Large Charming Historic House close to Beaches
Fridge, microwave, oven, dishwasher

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (23)
"This was the BEST decision for our family. The house was very cozy, old charm feel with some modern updates. The downstairs bathroom had a Spa vibe. We loved the 6 bedrooms & spacious kitchen & dining room. Loved how close it was to food & entertainment. The walk to the beach was only 10 minutes & very safe. We are use to blinds and/or shades, so just having light curtains for the windows was"
Large Charming Historic House close to Beaches
Cozy Westbrook Vacation Rental - Walk to Beach!
Fridge, microwave, stovetop, dishwasher

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (14)
"Perfect off season weekend for us with easy access to walks on the beach and lots of relaxing!"
Cozy Westbrook Vacation Rental - Walk to Beach!
New Madison beach house - Ocean front- Great views- booking Summer 2025
Fridge, microwave, oven, stovetop

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (57)
"The house really sits on its beach with a rock surrounded natural pool at high tide. The weather was CRAZY with rain and wind. The house held the temperature and was comfortable as the temps dropped below freezing! FYI the 4th bedroom with the trundle bed hasn’t a door so hence not a lot of privacy. But we were all good friends;) it was a comfortable space for 5 women who were good friends"
New Madison beach house - Ocean front- Great views- booking Summer 2025
Charming Village home in the heart of Southampton
Smart TV

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (20)
"We loved our stay! The location was perfect for our family, so easy to walk to town, close to the beach and easy to get to other towns. House was perfect as well, we didn’t get to enjoy the outdoors due to rain but loved the indoor space. Plenty of places to hang and enjoy/relax. Hoping to visit again soo!"
Charming Village home in the heart of Southampton
Waterfront Beach House
Terrace/patio

Waterfront Beach House

9.6 out of 10, Exceptional, (42)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House
Cozy House less than two miles from Ocean Beaches
Terrace/patio

Cozy House less than two miles from Ocean Beaches

10.0 out of 10, Exceptional, (5)
"The house was everything we needed for a weekend away! The house was very clean and cute esthetics. The back yard was great for the dogs. Claudea gave us great recommendations for places to eat. We would def rebook this house! "
Cozy House less than two miles from Ocean Beaches
Stunning Hampton Holiday Family Fantasy for your Team
TV, fireplace, video library, stereo

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (67)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (19)
"Perfect spot for a girls weekend! Property/house as advertised, and the house was fully stocked with all amenities. Thanks for a wonderful stay!! "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Fridge, microwave, oven, stovetop

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (89)
"Tuvimos un finde increíble en la casa, súper cómoda y bonita "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach House
Exterior

Beach House

9.8 out of 10, Exceptional, (51)
"We had such a great experience here! Joseph was so gracious and responsive and went above and beyond to make our stay great. His place is so cute with a mix of whimsical and really convenient touches. Our dog loved the yard, too! The neighborhood is gorgeous, too. We wished we had more time to explore the area and to take advantage of all the house has to offer. "
Beach House
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort
Fridge, microwave, oven, stovetop

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (55)
"Lovely, spacious and clean. We spent our Christmas holiday together with our family and the house was spacious and spotless. We had 5 adults with 2 small children in house. We hosted Christmas dinner for us and local family. Great space. Would love to rent in summer months to utilize outdoor space"
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
3 bedrooms, WiFi, bed sheets

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
Magic Place
Smart TV, video games

Magic Place

The price is SAR 1,689
SAR 3,410 total
includes taxes & fees
14 Apr - 15 Apr
Magic Place
Charming and Spacious Wainscott Home close to Town and Beaches, Great for...
A heated pool

Charming and Spacious Wainscott Home close to Town and Beaches, Great for...

Charming and Spacious Wainscott Home close to Town and Beaches, Great for...
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

North Fork 7 Bedroom Farmhouse Escape
Terrace/patio

North Fork 7 Bedroom Farmhouse Escape

3.0 star property
9.4 out of 10, Exceptional, (3)
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could walk to the beach, but be aware that it’s down the busy road as someone else mentioned. It wasn’t luxurious, but everything was clean and comfortable. I appreciated that towels and linens were provided...
North Fork 7 Bedroom Farmhouse Escape
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"Condo was great, family of 5 , clean, no hassle"
The price is SAR 536
SAR 694 total
includes taxes & fees
13 Apr - 14 Apr
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Condo | 2 bedrooms, iron/ironing board, free WiFi

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is SAR 541
SAR 781 total
includes taxes & fees
30 Apr - 1 May
Cliffside Resort Condominiums
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.