Southold Hotels with Swimming Pool

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Check availability on Southold Hotels with Swimming Pools

Tonight
31 Jul - 1 Aug
Tomorrow
1 Aug - 2 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Top Southold Hotels with Swimming Pools

Clinton Motel
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (261)
"For the money this reservation was a real win Clean lovely pool area convenient to everything"
The price is RM335
RM385 total
includes taxes & fees
31 Aug - 1 Sept
Clinton Motel
Econo Lodge Inn & Suites Old Saybrook Westbrook
Surrounded by lush greenery, a serene pond with a central fountain offers a peaceful escape.

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (439)
"Room was very comfortable. I would definitely use again."
The price is RM341
RM392 total
includes taxes & fees
6 Aug - 7 Aug
Econo Lodge Inn & Suites Old Saybrook Westbrook
Quality Inn Old Saybrook - Westbrook
Relax by the oval-shaped pool surrounded by lounge chairs and a high ceiling with a grid-like pattern.

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1001)
"Great location and pool, close to a wonderful restaurant "
The price is RM468
RM538 total
includes taxes & fees
10 Aug - 11 Aug
Quality Inn Old Saybrook - Westbrook
Wainscott Woods Retreat
Exterior

Wainscott Woods Retreat

2.0 star property
10.0 out of 10, Exceptional, (1)
"HIDDEN GEM IN THE HEART OF HAMPTONS! What a special place to stay in the Hamptons! I am so happy we found this wonderful gem! This hotel is clean, quiet and well managed. The pool is beautiful the rooms are modern, sleek and clean! The grounds are beautifully manicured. The location is perfect! This new hotel has the charm of a bed and breakfast. The hotel is a short car ride from either East Hampton or Southampton which is perfect if you chose to explore all the little towns the Hampton's has...
The price is RM4,965
RM5,672 total
includes taxes & fees
10 Aug - 11 Aug
Wainscott Woods Retreat
Greenporter Hotel
Relax by the fire pit surrounded by comfortable seating and a serene pool view.

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (148)
"Great place "
Greenporter Hotel
Hampton's Vacation Inn
Relax by the pool with lounge chairs and a shaded seating area nearby.

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (293)
"Great place highly recommended. Quiet and cozy atmosphere. Pool, tennis court, volleyball court and onsite parking made the stay that much better. Amazing staff and super professional. "
The price is RM1,012
RM1,156 total
includes taxes & fees
3 Aug - 4 Aug
Hampton's Vacation Inn
The Bentley Hotel Southampton
Relax by the pool surrounded by a scenic view and lounge in style on the tiled deck.

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (300)
"Great place!"
The price is RM1,205
RM1,498 total
includes taxes & fees
19 Aug - 20 Aug
The Bentley Hotel Southampton
Budget Host East End Hotel in Riverhead
Relax by the rectangular pool surrounded by a tiled deck and lounge chairs.

Budget Host East End Hotel in Riverhead

2.0 star property
6.6 out of 10, (728)
"Nice place"
The price is RM439
RM502 total
includes taxes & fees
10 Aug - 11 Aug
Budget Host East End Hotel in Riverhead
Canoe Place Inn and Cottages
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (48)
"Wonderful stay! "
Canoe Place Inn and Cottages
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.

Top Southold Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Staff all very friendly and helpful"
Cynthia 1-night trip
Posted 16 hours ago
Hyatt Place Long Island East End

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 6 places to stay with pools. During your visit, you can explore sights such as Sparkling Pointe and Croteaux Vineyards, and then kick back and relax poolside at one of the accommodation options in Southold that guests like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Offers buffet, an indoor pool and free self parking. Quality Inn Old Saybrook - Westbrook: Offers 2 outdoor swimming pools, an indoor pool and a full-service spa. Greenview Inn Riverhead: Offers 2 outdoor tennis courts, a seasonal outdoor pool and continental. Pier Blue Inn Old Saybrook - Essex: Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Saybrook Point Resort & Marina: Hotel, 2-minute walk from The Hamptons Beaches. Features spa services, a seasonal outdoor pool and a snack bar/deli.
How many pool hotels are there in Southold?
Expedia has 6 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, Croteaux Vineyards and Osprey's Dominion 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.