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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Vacation Homes in Southold

Terrace/patio
Beautifully farmhouse

Beautifully farmhouse

Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
The price is SAR 2,252
SAR 4,409 total
includes taxes & fees
11 Dec - 12 Dec
Beautifully farmhouse
Dining
Designer East Hampton Farmhouse

Designer East Hampton Farmhouse

East Hampton North
The price is SAR 901
SAR 3,041 total
includes taxes & fees
7 Dec - 8 Dec
Designer East Hampton Farmhouse
Living area
4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi

4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi

East Hampton
The price is SAR 3,941
SAR 6,369 total
includes taxes & fees
31 Dec - 1 January 2026
4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round

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.
The price is SAR 282
SAR 3,307 total
includes taxes & fees
15 Dec - 16 Dec
Blackberry: Private home with jacuzzi year-round
Fridge, microwave, oven, stovetop
Gorgeous 5-Bedroom House in East Hampton

Gorgeous 5-Bedroom House in East Hampton

East Hampton
The price is SAR 8,258
SAR 16,108 total
includes taxes & fees
10 Dec - 11 Dec
Gorgeous 5-Bedroom House in East Hampton
Fridge, oven, stovetop, dishwasher
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Upscale Hamptons Home: 1 Mi to Sammys Beach!

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.
The price is SAR 2,628
SAR 4,653 total
includes taxes & fees
31 Dec - 1 January 2026
Upscale Hamptons Home: 1 Mi to Sammys Beach!
Private kitchen
Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition

Wainscott
The price is SAR 5,608
SAR 7,299 total
includes taxes & fees
5 Dec - 6 Dec
Cozy 5 Bedroom With Wi-fi And Air Condition
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
The price is SAR 16,892
SAR 24,000 total
includes taxes & fees
6 Dec - 7 Dec
Sag Harbor Water View w Dock 1.5ml from town
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
The price is SAR 15,011
SAR 23,187 total
includes taxes & fees
2 Jan - 3 January 2026
Spacious 5-bedroom house with water views and 2 houses from the bay.
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
East Lyme
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.
The price is SAR 440
SAR 1,370 total
includes taxes & fees
7 Dec - 8 Dec
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

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

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.
The price is SAR 15,325
SAR 27,248 total
includes taxes & fees
8 Dec - 9 Dec
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Pool
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Southampton
9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
The price is SAR 1,267
SAR 3,077 total
includes taxes & fees
5 Dec - 6 Dec
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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)
"Just finished a 5 day stay. Best house rental ever! Great and thoughtful hosts. Super relaxing and extremely luxurious! Highly recommend!"
United States
William H.
The price is SAR 4,328
SAR 6,039 total
includes taxes & fees
4 Jan - 5 January 2026
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.
The price is SAR 1,689
SAR 4,164 total
includes taxes & fees
5 Dec - 6 Dec
Minutes from the beach, brand new 4 bedroom
Property grounds
American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6

Greenport
2.0 out of 10, (1)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is SAR 859
SAR 1,278 total
includes taxes & fees
4 Jan - 5 January 2026
American Beech in Greenport - Deluxe King 6
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)
"Great job "
United States
emilio
The price is SAR 672
SAR 1,029 total
includes taxes & fees
4 Jan - 5 January 2026
American Beech in Greenport - Petite King Room 7
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, (4)
"Communication was excellent. "
United States
Katy C.
The price is SAR 324
SAR 1,512 total
includes taxes & fees
7 Dec - 8 Dec
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all

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.
The price is SAR 1,239
SAR 2,500 total
includes taxes & fees
7 Dec - 8 Dec
Charming Northfork Townhouse- walk to all
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)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is SAR 1,408
SAR 2,719 total
includes taxes & fees
7 Dec - 8 Dec
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

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Staff was courteous and the room was spotless. Food service is very good as well. "
Efrem 1-night trip
Posted 3 days ago
Hilton Garden Inn Riverhead