A calm lake with a forest in the background during sunset.

Search Hotels with Pool in Southold

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Southold Hotels with Pool

Tonight
14 Aug - 15 Aug
Tomorrow
15 Aug - 16 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Southold hotels with a pool

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
Rp5.024.330
Rp7.272.177 total
includes taxes & fees
9 Sept - 10 Sept
Sound View Greenport

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
Rp4.938.521
Rp6.561.315 total
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn

3. North Fork Resort

North Fork Resort
Greenport
Rp5.743.880
Rp6.562.382 total
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
Rp5.479.122
Rp7.853.724 total
includes taxes & fees
7 Sept - 8 Sept
Cliffside Resort Condominiums

5. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
Rp9.551.328
Rp12.003.605 total
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel

6. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
Rp5.653.601
Rp6.459.318 total
includes taxes & fees
17 Aug - 18 Aug
Shelter Island House

7. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
Rp3.021.213
Rp3.898.660 total
includes taxes & fees
7 Sept - 8 Sept
The Bentley Hotel Southampton

8. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
Rp5.818.963
Rp7.331.603 total
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate

9. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
Rp5.604.440
Rp6.403.184 total
includes taxes & fees
17 Aug - 18 Aug
West Neck Guesthouse

10. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
Rp1.412.283
Rp1.624.125 total
includes taxes & fees
2 Sept - 3 Sept
Clinton Motel
View all properties

Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Rooms were clean staff helpful would definitely go back"
Frank 2-night trip
Posted less than an hour ago
Saybrook Point Resort & Marina
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Booking process was very simple and easy"
Roberto 3-night trip
Posted 3 hours ago
The Atlantic Hotel
 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Perfect little spot in Hamptons Bay!"
Jessica 2-night trip
Posted 5 hours ago
Hampton's Vacation Inn
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Nice resort, very convenient. However, a little pricey and every time you turned around there was a gratuity. Food was ok, not great for the price paid though."
Russell 2-night trip
Posted 7 hours ago
Water's Edge Resort & Spa
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Place was charming and overall beautiful .. everything was wonderful.. definitely will stay again"
Mary 1-night trip
Posted 22 hours ago
The Hampton Maid
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Great vibe and decor. Super Cozy and elegant. Best Hamptons stay! Can’t wait to come back next year."
Joseph 1-night trip
Posted 1 day ago
Faraway Sag Harbor

Frequently asked questions

What's it like visiting Southold?
If laying by the pool is your idea of the perfect getaway, you may want to consider family-friendly Southold, which offers 5 places to stay with pools. During your visit, you can explore sights such as The Hamptons Beaches, and then kick back and relax poolside at one of the accommodation options in Southold that travellers like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Offers buffet, a seasonal outdoor pool and free self parking. Vine & Sand: Features a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Sound View Greenport: Features a seasonal outdoor pool, an indoor pool and a private beach. The Atlantic Hotel: Offers a private beach, a seasonal outdoor pool and a full-service spa.
How many pool hotels are there in Southold?
Expedia has 5 hotels in Southold for your poolside break.
What is there to see and do in Southold?
Enjoy a stroll along the shore at McCabe's Beach and Horton Lane Beach. Discover sights such as Sparkling Pointe, Mattebella Vineyards and Croteaux Vineyards during your stay.
When is the best time to book a hotel with a pool in Southold?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Southold in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or March, when the average temp is 3°C.
What's the best way to travel around Southold?
Knowing the transportation options in Southold can help you enjoy the area beyond your hotel pool. To see more of the larger area, hop on a train at Southold Station. Southold may not have many public transport options to choose from, so consider renting a car to explore more.

Explore a world of travel with Expedia