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  3. >United States
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  5. >Suffolk
  6. >Southold

Hotels with Outdoor Pool in Southold

200+ HOTELS IN AND AROUND SOUTHOLDRanking can be influenced by the commissions we receive.
Cedar-shake Cottage, Heated pool and Gardens main photo
Cedar-shake Cottage, Heated pool and Gardens
Vacation Home in Southold NYUS flag
$
+6
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Dog Friendly
Vine & Sand--Southold NY's Newest B&B main photo
Vine & Sand--Southold NY's Newest B&B
Bed & Breakfast in Southold NYUS flag
9.4
Excellent
From $540
$
+8
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Free Wi-Fi
18 more hotels nearby!
The Pridwin Hotel main photo
The Pridwin Hotel
2.8 mi from Southold
Hotel in Shelter Island NYUS flag
8.5
Very Good
From $697
$
+8
Outdoor Pool
Questionnaire
Answers last updated by The Pridwin Hotel
Location of the pool:Outdoor pool
Sandpoint by Rove Travel - 6BR Family Home with Pool main photo
Sandpoint by Rove Travel - 6BR Family Home with Pool
3.0 mi from Southold
Vacation Home in Shelter Island NYUS flag
10
Excellent
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Sound View Greenport main photo
Sound View Greenport
3.4 mi from Southold
Hotel in Greenport NYUS flag
8.2
Very Good
From $241
$
+8
Outdoor Pool
AI-generatedFeatures a seasonal outdoor pool with sun loungers and pool umbrellas. Guests have direct access to a private beach and can enjoy a poolside bar.
Shelter Island House main photo
Shelter Island House
3.5 mi from Southold
Hotel in Shelter Island Heights NYUS flag
9.2
Excellent
From $230
$
+7
Outdoor Pool
AI-generatedFeatures a seasonal outdoor swimming pool set within a garden. Guests can also access a shared lounge, restaurant, and snack bar on the property.
Questionnaire
Answers last updated by Shelter Island House
Seven Resort Style Inn near Beach main photo
Seven Resort Style Inn near Beach
3.6 mi from Southold
Bed & Breakfast in Shelter Island Heights NYUS flag
9.8
Excellent
From $379
$
+11
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
4 Star
The Cliffside Resort Condominiums main photo
The Cliffside Resort Condominiums
3.7 mi from Southold
Apartments in Greenport NYUS flag
9.2
Excellent
From $302
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Hotel Moraine main photo
Hotel Moraine
3.8 mi from Southold
Hotel in Greenport NYUS flag
9.4
Excellent
From $416
$
+11
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Golf
North Fork Resort main photo
North Fork Resort
4.0 mi from Southold
Campground in Greenport NYUS flag
9.2
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Harbor Knoll Bed and Breakfast main photo
Harbor Knoll Bed and Breakfast
4.5 mi from Southold
Bed & Breakfast in Greenport NYUS flag
10
Excellent
From $495
$
+5
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Free Wi-Fi
Cozy Greenport Cottage main photo
Cozy Greenport Cottage
4.5 mi from Southold
Vacation Home in Greenport NYUS flag
9.0
Excellent
From $575
$
+5
Info
Categories
Outdoor Pool
Pool
Heated Pool
Private Pool
Outdoor Pool
Free Wi-Fi
Dering Harbor Inn main photo
Dering Harbor Inn
4.5 mi from Southold
Hotel in Shelter Island Heights NYUS flag
From $8
$
+7
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Honeymoon
Oyster Estate main photo
Oyster Estate
4.5 mi from Southold
Hotel in Greenport NYUS flag
8.8
Excellent
From $343
$
+11
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Parking
EV charging stations
The Harbor Front Inn main photo
The Harbor Front Inn
4.7 mi from Southold
Hotel in Greenport NYUS flag
8.7
Very Good
From $188
$
+6
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Golf
Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces main photo
Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces
5.4 mi from Southold
Vacation Home in Sag Harbor NYUS flag
Currently inactive on our platform.
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Meadowood Manor by Rove Travel - 6BR Outdoor Spaces main photo
Meadowood Manor by Rove Travel - 6BR Outdoor Spaces
5.7 mi from Southold
Vacation Home in Sag Harbor NYUS flag
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Respite Ranch Pool, Hot Tub & North Fork main photo
Respite Ranch Pool, Hot Tub & North Fork
6.0 mi from Southold
Vacation Home in Mattituck NYUS flag
9.0
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Private Pool
Outdoor Pool
Dog Friendly
Villa Sapphire Bay main photo
Villa Sapphire Bay
6.0 mi from Southold
Villa in Sag Harbor NYUS flag
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Villa Zainip - Luxury with pool main photo
Villa Zainip - Luxury with pool
6.1 mi from Southold
Villa in Sag Harbor NYUS flag
10
Excellent
From $2,927
$
+5
Info
Categories
Outdoor Pool
Pool
Private Pool
Outdoor Pool
Luxury
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 200+ hotels in and around Southold
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