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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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)
"Spa was fantastic, rooms are nothing extravagant but clean and well maintained. Everyone was polite, great stay"
The price is AED 768
AED 946 total
includes taxes & fees
14 May - 15 May
Water's Edge Resort & Spa
Ocean Colony Beach and Tennis Club
Cozy Pad 2BR Beachside Home | TennisPoolFreePKG Unit 721 | Terrace/patio

Ocean Colony Beach and Tennis Club

2.0 star property
Ocean Colony Beach and Tennis Club
Available July 21-28, 2023
Indoor pool, a heated 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
Indoor pool, a heated 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
Indoor pool, outdoor 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 4
Indoor pool, a heated 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 and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Indoor pool, a heated 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
Indoor pool, outdoor 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 & Spa May 23, 2025 - May 30, 2025
Pool

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025
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)
"Nice property, extremely helpful Owner. Great kitchen"
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, (284)
"Love the ocean view from the balcony"
The price is AED 565
AED 725 total
includes taxes & fees
15 May - 16 May
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (215)
"Great place. "
The price is AED 769
AED 1,038 total
includes taxes & fees
26 May - 27 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.

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?
Our top-rated resort 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.
What can I do in Southold?
Sparkling Pointe, Croteaux Vineyards, and Horton Lane Beach are a few of the interesting sights to visit. Osprey’s Dominion 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.