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Search Vacation Homes in Southold

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Southold vacation homes

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

Vacation Home in Old Lyme

10.0 out of 10, Exceptional, (4)
"Communication was excellent. "
United States
Katy C.
$358 nightly
The price is $404
Dec 11 - Dec 12
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

2.0 star property
9.0 out of 10, Wonderful, (4)
"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)."
United States
Sarah G.
$325 nightly
The price is $367
Dec 10 - Dec 11
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Vacation Home in Water Mill

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,353 nightly
The price is $7,259
Dec 10 - Dec 11
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Fridge, microwave, oven, stovetop
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins

Vacation Home in Clinton

2.0 star property
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
$451 nightly
The price is $510
Dec 14 - Dec 15
Total with taxes and fees
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
$771 nightly
The price is $881
Dec 15 - Dec 16
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in Hampon Bays

9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,113 nightly
The price is $1,272
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$463 nightly
The price is $523
Dec 16 - Dec 17
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop
Adorable Cottage, 5 min walk to water & town

Vacation Home in Westbrook Center

9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$368 nightly
The price is $416
Dec 10 - Dec 11
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.

Vacation Home in Sag Harbor

$5,642 nightly
The price is $6,446
Dec 14 - Dec 15
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Private kitchen
Stylish Modern Stay Steps from the Ocean

Vacation Home in Clinton

10.0 out of 10, Exceptional, (1)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
$298 nightly
The price is $337
Dec 11 - Dec 12
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
Terrace/patio
American Beech in Greenport - Petite King Room 7

Vacation Home in Greenport

9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$242 nightly
The price is $277
Dec 10 - Dec 11
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
5 bedrooms, iron/ironing board, WiFi, bed sheets
Sag Harbor Water View w Dock 1.5ml from town

Vacation Home in Bay Point

$5,596 nightly
The price is $6,393
Dec 12 - Dec 13
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Vacation Home in Saybrook Manor

9.6 out of 10, Exceptional, (133)
"Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back. "
United States
Rob C.
$512 nightly
The price is $580
Dec 10 - Dec 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

Vacation Home in Calverton

2.0 star property
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
$582 nightly
The price is $665
Dec 10 - Dec 11
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Fridge, microwave, oven, stovetop
4-bedroom beach house minutes from Hamptons

Vacation Home in Calverton

2.0 star property
$583 nightly
The price is $666
Dec 14 - Dec 15
Total with taxes and fees
4-bedroom beach house minutes from Hamptons
Microwave, oven, stovetop, dishwasher
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR

Vacation Home in Clinton

2.0 star property
$181 nightly
The price is $205
Dec 10 - Dec 11
Total with taxes and fees
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR
Fridge, microwave, oven, stovetop
Charming Northfork Townhouse- walk to all

Vacation Home in Greenport

10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
$594 nightly
The price is $679
Dec 10 - Dec 11
Total with taxes and fees
Charming Northfork Townhouse- walk to all
Terrace/patio
Immaculate Waterfront 2 bedroom!

Vacation Home in Hampton Bays

10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
$562 nightly
The price is $642
Dec 10 - Dec 11
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Fridge, oven, stovetop, dishwasher
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Vacation Home in East Hampton

9.4 out of 10, Exceptional, (3)
"Wonderful property. Lisette was a fantastic host and her home updated and modern. "
United States
Joanna D.
$1,085 nightly
The price is $1,240
Dec 31 - Jan 1, 2026
Total with taxes and fees
Upscale Hamptons Home: 1 Mi to Sammys Beach!
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated

Vacation Home in Greenport

9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
$629 nightly
The price is $719
Dec 10 - Dec 11
Total with taxes and fees
Northfork Townhouse- walk to all/ newly renovated
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 Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"Great sta"
Brandon 2-night trip
Posted 21 hours ago
The Shoals Suites and Slips

Find out more about Southold

Southold Vacation Homes information

Number of reviews
165
Accommodation
1733 Vacation Homes
Lowest Price
$277
Highest Price
$7,259

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