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Compare 9 Resorts in Southold with updated reviews, rates, and availability.

Water's Edge Resort & Spa
Exterior

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1000)
"Breathtaking property with fabulous service"
The price is SAR 748
SAR 924 total
includes taxes & fees
1 Jan - 2 January 2025
Water's Edge Resort & Spa
Ocean Colony Beach and Tennis Club
Terrace/patio

Ocean Colony Beach and Tennis Club

2.0 star property
Ocean Colony Beach and Tennis Club
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Available July 21-28, 2023
Pool

Available July 21-28, 2023

8.8 out of 10, Excellent, (3)
"This rental was absolutely perfect. Room was exactly as described and very clean and well maintained. Very short walk to beach and pool. Water’s Edge staff was extremely courteous and attentive. The grounds are gorgeous and well maintained. The pool and beach combo was perfect for a family with kids. The owner of this rental was very easy to communicate with and responded quickly. We have zero complaints. We will absolutely be back again!"
Available July 21-28, 2023
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

8.0 out of 10, Very Good, (1)
"Comfortable space for a small family. We liked the flexibility of having a small beach on property and our own kitchen. The owner was easy to contact too."
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

10.0 out of 10, Exceptional, (1)
"Had a great stay for a long weekend getaway! The unit was in great shape, and we really enjoyed ourselves!"
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4
Pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4
Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)
Pool

Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)

Water's Edge Resort & Spa (May 17, 2024 - May 24, 2024)
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, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is SAR 474
SAR 623 total
includes taxes & fees
5 Jan - 6 January 2025
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Room

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"
Cliffside Resort Condominiums
Gorgeous private Hamptons house with pool and volleyball court
Exterior

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very Good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court
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.

Frequently asked questions

What can I expect from a resort vacation in Southold?
You deserve some time off, and a resort is the perfect place to find all the services and amenities you need for a relaxing time in Southold. One of the comfortable resort hotels in the surrounding area could be just what you’re searching for, whether you want an amazing pool, blissful spa treatments, or nightly entertainment options.
What's a favorite resort for my stay in Southold?
Here are our top-rated resorts near Southold: Water’s Edge Resort & Spa - Beach resort. 15 mi (24.1 km) from Southold. Features 3 restaurants, a private beach, and a full-service spa. Highly rated for its great beach location. Ocean Colony Beach and Tennis Club - Beach resort. 20.2 mi (32.5 km) from Southold. Has a seasonal outdoor pool, a garden, and free self parking. Water’s Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6 - Beach resort. 14.9 mi (24 km) from Southold. Enjoy the sauna, fitness center, and beach sun loungers. Available July 21-28, 2023 - Family-friendly resort. 14.9 mi (24 km) from Southold. Amenities include a sauna, a fitness center, and concierge services. Water’s Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6 - Beach resort. 14.9 mi (24 km) from Southold. Access to a sauna, a fitness center, and beach sun loungers.
What can I do in Southold?
Sparkling Pointe, Croteaux Vineyards, and Horton Lane Beach are a few of the interesting sights to visit. Corey Creek Winery and Sannino’s Bella Vita Vineyard are a few additional attractions in the area that you might like.
What's the seasonal weather like in Southold?
The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.
What's the best way to get to and around Southold?
Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) from the heart of the city. You can also search for flights into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. If you want to venture outside of the area, hop aboard a train at Southold Station.