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Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Vacation Homes in Southold

Our top choices for Southold vacation homes

Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (2)
"good experience"
The price is ￥88,434
￥173,110 total
includes taxes & fees
Aug 25 - Aug 26
Beautifully farmhouse
Stunning Southampton Village Modern Home
Living area

Stunning Southampton Village Modern Home

The price is ￥1,989,765
￥2,433,618 total
includes taxes & fees
Aug 23 - Aug 24
Stunning Southampton Village Modern Home
Sag Harbor Water View w Dock 1.5ml from town
5 bedrooms, iron/ironing board, WiFi, bed sheets

Sag Harbor Water View w Dock 1.5ml from town

The price is ￥810,645
￥1,134,633 total
includes taxes & fees
Sep 10 - Sep 11
Sag Harbor Water View w Dock 1.5ml from town
Rogers Lake House (87) · CT College+Beach+USCGA
Property grounds

Rogers Lake House (87) · CT College+Beach+USCGA

10.0 out of 10, Exceptional, (2)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
The price is ￥29,633
￥80,628 total
includes taxes & fees
Sep 9 - Sep 10
Rogers Lake House (87) · CT College+Beach+USCGA
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Beach nearby, sun loungers, beach towels

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.8 out of 10, Exceptional, (6)
"We were here to attend a family member’s wedding. The Check-in process was quite simple as was the checkout. Quiet neighborhood. Would book this property for other events."
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Spacious 5-bedroom house with water views and 2 houses from the bay.
Beach

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is ￥589,560
￥950,918 total
includes taxes & fees
Aug 26 - Aug 27
Spacious 5-bedroom house with water views and 2 houses from the bay.
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
9.0 out of 10, Wonderful, (2)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
The price is ￥27,733
￥67,250 total
includes taxes & fees
Aug 27 - Aug 28
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Shoreline Oasis
Exterior

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is ￥26,383
￥38,852 total
includes taxes & fees
Sep 4 - Sep 5
Shoreline Oasis
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Terrace/patio

Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
The price is ￥397,953
￥807,783 total
includes taxes & fees
Sep 3 - Sep 4
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Aqua by American Beech - Rooftop Suite
Terrace/patio

Aqua by American Beech - Rooftop Suite

10.0 out of 10, Exceptional, (1)
"Quick stay after a day at the wineries. Location is is set in a beautiful quiet area and the view is just amazing. The staff could truly not be any better, any request or issue was dealt with in literally a minute. Room was perfect, clean and made you feel at home with anything you needed. Will definitely be back!"
The price is ￥58,219
￥82,515 total
includes taxes & fees
Sep 9 - Sep 10
Aqua by American Beech - Rooftop Suite
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Great place! Great communication with property owner!"
The price is ￥44,836
￥84,571 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
9.0 out of 10, Wonderful, (4)
"Large open first floor for a large family stay. Great back patio with a nice view of the river. Don't miss the morning swans. "
The price is ￥73,548
￥133,536 total
includes taxes & fees
Sep 1 - Sep 2
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Huge Island Getaway Pool Hot Tub Walk To Beach
Beach nearby

Huge Island Getaway Pool Hot Tub Walk To Beach

10.0 out of 10, Exceptional, (7)
"Property great. Beautiful home with great amenities"
The price is ￥294,633
￥404,144 total
includes taxes & fees
Sep 1 - Sep 2
Huge Island Getaway Pool Hot Tub Walk To Beach
adorable ranch in beach community
Beach nearby

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is ￥32,426
￥70,526 total
includes taxes & fees
Sep 15 - Sep 16
adorable ranch in beach community
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Outdoor pool, a heated pool

6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

10.0 out of 10, Exceptional, (42)
"the property was lovely and well equipped with all amenties. Comfortable and located in an area which is accessible for all towns in the Hamptons"
The price is ￥406,944
￥656,061 total
includes taxes & fees
Sep 16 - Sep 17
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Cozy quiet gem, private & fenced in backyard
Fridge, microwave, oven, stovetop

Cozy quiet gem, private & fenced in backyard

9.4 out of 10, Exceptional, (3)
"good times"
The price is ￥88,287
￥230,701 total
includes taxes & fees
Aug 24 - Aug 25
Cozy quiet gem, private & fenced in backyard
Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is ￥118,664
￥213,023 total
includes taxes & fees
Sep 14 - Sep 15
Work and Play Special! Extended Stay Discount
Private beach on a fenced in property sunset views
Terrace/patio

Private beach on a fenced in property sunset views

10.0 out of 10, Exceptional, (10)
"Beautiful sunrise, sunsets and scenery. Beautiful property"
The price is ￥294,633
￥492,886 total
includes taxes & fees
Aug 24 - Aug 25
Private beach on a fenced in property sunset views
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
Outdoor pool, a heated pool

Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons

10.0 out of 10, Exceptional, (56)
"We had a very nice stay at Stan's house. We spent the majority of our time relaxing in the beautiful backyard. The pool is amazing!"
The price is ￥151,297
￥325,037 total
includes taxes & fees
Aug 25 - Aug 26
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is ￥35,226
￥52,709 total
includes taxes & fees
Sep 1 - Sep 2
American Beech in Greenport - Petite King Room 7
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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Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"The staff was excellent. Very friendly and accommodating. And the room was comfortable and clean."
Brian 1-night trip
Posted 10 hours ago
Pier Blue Inn Old Saybrook - Essex