Search Vacation Homes in Southold

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Vacation Homes in Southold

Terrace/patio
Beautifully farmhouse

Beautifully farmhouse

Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
$1,028 nightly
The price is $1,175
Nov 10 - Nov 11
Total with taxes and fees
Beautifully farmhouse
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

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

Old Lyme
10.0 out of 10, Exceptional, (3)
"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!"
United States
Hemie J.
$356 nightly
The price is $403
Nov 10 - Nov 11
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
Cozy quiet gem, private & fenced in backyard

Cozy quiet gem, private & fenced in backyard

East Hampton
9.4 out of 10, Exceptional, (3)
"Just hubby & I. Great fireplace and deck with very clean bubbly hot tub. Comfy king-sized bed. Kitchen was clean & functional with basics. Backyard appeared larger in pictures. Rental could use extra couch in living room to comfortably fit eight ppl. The living room couch is just for sitting, appears larger in pictures. Couch is"
United States
STEPHANIE C.
$771 nightly
The price is $881
Nov 10 - Nov 11
Total with taxes and fees
Cozy quiet gem, private & fenced in backyard
Beach nearby
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
$234 nightly
The price is $265
Nov 30 - Dec 1
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Terrace/patio
Year-Round Private Jacuzzi / Peaceful Fenced Yard

Year-Round Private Jacuzzi / Peaceful Fenced Yard

Hampon Bays
9.6 out of 10, Exceptional, (22)
"What a great place for a family gathering! The backyard is to die for and the host was very helpful throughout the stay. We’ll be back!!"
United States
Lisa w.
$1,113 nightly
The price is $1,272
Nov 16 - Nov 17
Total with taxes and fees
Year-Round Private Jacuzzi / Peaceful Fenced Yard
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Water Mill
10.0 out of 10, Exceptional, (6)
"Our family / extended family was in town for over a week for the Hampton Classic horse show. We all enjoyed or stay at this wonderful home: beautiful newly renovated open space, outstanding kitchens (indoors and outdoors), numerous areas to have separate down time, excellent in suite bedroom / bathrooms including three bedrooms suites with king beds, fabulous backyard with a private pool, and exceptionally clean with all amenities needed. The owners were also incredible; extremely responsive,...
United States
Kristin C.
$4,797 nightly
The price is $5,481
Nov 10 - Nov 11
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green

2.0 star property
Westbrook
$405 nightly
The price is $458
Nov 11 - Nov 12
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio
Private beach on a fenced in property sunset views

Private beach on a fenced in property sunset views

Hampton Bays
10.0 out of 10, Exceptional, (12)
"Beautiful sunrise, sunsets and scenery. Beautiful property"
United States
Elaine P.
$1,170 nightly
The price is $1,337
Nov 10 - Nov 11
Total with taxes and fees
Private beach on a fenced in property sunset views
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$245 nightly
The price is $280
Nov 10 - Nov 11
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Saybrook Manor
9.6 out of 10, Exceptional, (133)
"We thoroughly enjoyed our stay...the historic home was a perfect New England getaway for our group of women."
United States
Shari M.
$448 nightly
The price is $508
Nov 10 - Nov 11
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
Calverton
8.6 out of 10, Excellent, (8)
"A fantastic location, and would certainly stay again! The bed was a bit hard but we all like something different. "
United States
Ethan L.
$582 nightly
The price is $665
Nov 10 - Nov 11
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Terrace/patio
Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!

Hampton Bays
10.0 out of 10, Exceptional, (5)
"Highly recommend. Very close to the beach. Cute updated little home. We loved it!"
United States
Gail R.
$563 nightly
The price is $643
Nov 10 - Nov 11
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Fridge, microwave, oven, stovetop
Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass

Guilford
9.2 out of 10, Wonderful, (90)
"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."
United States
Jennifer D.
$384 nightly
The price is $435
Nov 25 - Nov 26
Total with taxes and fees
Historic New England home ,Reunions Beach pass
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.

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

Sag Harbor
$5,642 nightly
The price is $6,446
Nov 14 - Nov 15
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated

Greenport
9.6 out of 10, Exceptional, (9)
"Very clean and walking distance to all a great vacation space i would recommend to anyone looking to experience the east end."
United States
Dana G.
Northfork Townhouse- walk to all/ newly renovated
Property grounds
Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island
10.0 out of 10, Exceptional, (52)
"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "
United States
moshe A.
$1,165 nightly
The price is $1,331
Nov 11 - Nov 12
Total with taxes and fees
Work and Play Special! Extended Stay Discount
A heated pool
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Southampton
10.0 out of 10, Exceptional, (15)
"The house was great! Super spacious and clean and looks even better than the pictures. Lots of amenities like a washer and dryer, umbrellas for the pool, dishes and some stocked items in the fridge. I connected with Anne and she was incredible and super flexible, as well as responsive to all of our questions and requests. The area is also super pretty and peaceful."
United States
Tina
$2,028 nightly
The price is $2,108
Nov 10 - Nov 11
Total with taxes and fees
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Fridge, microwave, oven, stovetop
Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom

Southampton
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
$971 nightly
The price is $1,109
Nov 11 - Nov 12
Total with taxes and fees
Minutes from the beach, brand new 4 bedroom
5 bedrooms, iron/ironing board, WiFi, bed sheets
Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town

Bay Point
$5,594 nightly
The price is $6,391
Nov 12 - Nov 13
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Outdoor dining
Gorgeous 5-Bedroom House in East Hampton

Gorgeous 5-Bedroom House in East Hampton

East Hampton
$3,748 nightly
The price is $4,282
Nov 17 - Nov 18
Total with taxes and fees
Gorgeous 5-Bedroom House in East Hampton
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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"From the front desk receptionist to checking out, everything was perfect. "
Eileen 1-night trip
Posted 19 hours ago
The Bentley Hotel Southampton

Find out more about Southold

Southold Vacation Homes information

Number of reviews
303
Accommodation
1800 Vacation Homes
Lowest Price
$265
Highest Price
$6,446

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