Search Vacation Homes in Village of Southampton

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Vacation Homes in Village of Southampton

A heated pool
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Vacation Home in 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.
$1,604 nightly
The price is $1,707
Jan 1 - Jan 2, 2026
Total with taxes and fees
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Pool
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Vacation Home in 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.
$718 nightly
The price is $820
Dec 3 - Dec 4
Total with taxes and fees
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Fridge, microwave, oven, stovetop
Minutes from the beach, brand new 4 bedroom

Vacation Home in Southampton

10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
$971 nightly
The price is $1,109
Dec 4 - Dec 5
Total with taxes and fees
Minutes from the beach, brand new 4 bedroom
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 3 - Dec 4
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
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 7 - Dec 8
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
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.
$1,142 nightly
The price is $1,305
Dec 20 - Dec 21
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

10.0 out of 10, Exceptional, (12)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,085 nightly
The price is $1,240
Dec 7 - Dec 8
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
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 5 - Dec 6
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
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 3 - Dec 4
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Terrace/patio
American Beech in Greenport - Petite King Room 7

Vacation Home in Greenport

9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
$243 nightly
The price is $278
Dec 7 - Dec 8
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
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 3 - Dec 4
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
$540 nightly
The price is $617
Dec 3 - Dec 4
Total with taxes and fees
4-bedroom beach house minutes from Hamptons
Private kitchen
Cozy 5 Bedroom With Wi-fi And Air Condition

Vacation Home in Wainscott

$1,699 nightly
The price is $1,941
Dec 3 - Dec 4
Total with taxes and fees
Cozy 5 Bedroom With Wi-fi And Air Condition
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 3 - Dec 4
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
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.
Charming Northfork Townhouse- walk to all
Property grounds
Beachfront Greenport Villa

Vacation Home in Greenport

9.6 out of 10, Exceptional, (10)
"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"
United States
Melissa F.
Beachfront Greenport Villa
Property grounds
Work and Play Special! Extended Stay Discount

Vacation Home in Shelter Island

10.0 out of 10, Exceptional, (53)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
Work and Play Special! Extended Stay Discount
Terrace/patio
Beautifully farmhouse

Vacation Home in Southold

10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
$1,027 nightly
The price is $1,173
Dec 3 - Dec 4
Total with taxes and fees
Beautifully farmhouse
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.
Northfork Townhouse- walk to all/ newly renovated
Smart TV, fireplace, foosball, table tennis
Cozy Hamptons Escape 3BR Minutes From Beach!

Vacation Home in Hampton Bays

9.2 out of 10, Wonderful, (5)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
$792 nightly
The price is $905
Dec 3 - Dec 4
Total with taxes and fees
Cozy Hamptons Escape 3BR Minutes From Beach!
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 Village of Southampton Hotel Reviews

Southampton Inn

Southampton Inn

10/10 Excellent
"Very clean and nice room"
Elie 2-night trip
Posted 8 days ago
Southampton Inn

Find out more about Village of Southampton

Village of Southampton Vacation Homes information

Number of reviews
152
Accommodation
1712 Vacation Homes
Lowest Price
$278
Highest Price
$7,259

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