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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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 🏖
Outdoor dining

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, (81)
"It was a very nice stay. Sound of the ocean was calming. We would go back. "
Waterfront House with picture-perfect views from all 3 levels.
Stunning New Designer Renovation
View from property

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, (169)
"This property overall is as stated in the description. 6 bedrooms, 5 bathrooms on a quiet cul-de-sac. The home is equipped to accommodate a large party of people, including things to keep little children busy.The master bedroom suite is huge and all the other rooms are a good size & comfortable.There are a few things to take note of, because this is a rental the sofas on the main floor and lower level were stained ( both are beige), I took sheets and covered them prior to sitting.Some of the...
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
Sprawling Southampton Home: Private Pool
Beach nearby

Sprawling Southampton Home: Private Pool

9.0 out of 10, Wonderful, (44)
"My family and I had a wonderful stay at this property. The house was well-situated in a quiet neighborhood - very private, surrounded by trees and a few wild turkeys. There were many amenities that made our stay enjoyable from the large patio and pool, 3 full baths in the main house, one of which had an amazing shower system with body spray, and a designated work area for those that can’t leave work behind. Communication with the property manager was easy and Debbie was very helpful and...
Sprawling Southampton Home: Private Pool
Cozy Westbrook Vacation Rental - Walk to Beach!
Aerial view

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (13)
"My college friends and I try to get away a few times a year and our latest weekend trip was to Westbrook. I love the Connecticut shore any time of year but off season is my favorite (very affordable hahaha). I was so happy when I walked into this house - sooooo clean, it had everything we needed in the kitchen, comfortable beds, and a very responsive host (thank you Wendy!). Even though it was March we were lucky enough to bundle up and enjoy coffee out on the patio! I can’t say enough about...
Cozy Westbrook Vacation Rental - Walk to Beach!
New Madison beach house - Ocean front- Great views- booking Summer 2025
Exterior

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

10.0 out of 10, Exceptional, (56)
"Great location "
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
Sun loungers

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, (66)
"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
Beach nearby, sun loungers, beach towels

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

9.0 out of 10, Wonderful, (88)
"Everything was just fine - nothing spectacular but good enough for a short stay. Extremely safe feeling location"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach House
Beach nearby, sun loungers, beach towels

Beach House

9.8 out of 10, Exceptional, (50)
"Wonderful location. Cozy space we had a wonderful time"
Beach House
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge
Fridge, microwave, oven, stovetop

Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

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 spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge
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 AED 1,653
AED 2,920 total
includes taxes & fees
31 Mar - 1 Apr
Magic Place
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
Beach nearby

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
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Great cozy place"
The price is AED 484
AED 633 total
includes taxes & fees
31 Mar - 1 Apr
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

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 AED 636
AED 887 total
includes taxes & fees
13 Apr - 14 Apr
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.