Holiday Homes in Southampton

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Southampton holiday homes

Terrace/patio

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton
9.8 out of 10, Exceptional, (21 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is €730
includes taxes & fees
3 Jun - 4 Jun
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Living area

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
The price is €1,147
includes taxes & fees
4 Jun - 5 Jun
Minutes from the beach, brand new 3 bedroom
Outdoor pool, a heated pool

US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.

US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.
Southampton
10.0 out of 10, Exceptional, (23 reviews)
"Great property as advertised!!"
United States
robert b.
The price is €3,166
includes taxes & fees
20 Jun - 21 Jun
US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.
Exterior

Gorgeously Renovated SH Village 5 bd w/ Large Pool

Gorgeously Renovated SH Village 5 bd w/ Large Pool
Southampton
8.8 out of 10, Excellent, (6 reviews)
"Spacious and great location. Cleanliness and "
United States
Harry D.
The price is €4,964
includes taxes & fees
17 Jun - 18 Jun
Gorgeously Renovated SH Village 5 bd w/ Large Pool
Terrace/patio

Tennis & Sea Escape - Hydrangeas in the Hamptons

Tennis & Sea Escape - Hydrangeas in the Hamptons
Westhampton Beach
The price is €331
includes taxes & fees
15 Jun - 16 Jun
Tennis & Sea Escape - Hydrangeas in the Hamptons
Outdoor dining

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
The price is €546
includes taxes & fees
4 Jun - 5 Jun
Hampton Bays Townhouse - Pool, Beach Access
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
Westhampton Beach
10.0 out of 10, Exceptional, (210 reviews)
"Great host, everything that we needed for our trip was available, ample room for the 9 of us."
United States
matthew p.
The price is €819
includes taxes & fees
4 Jun - 5 Jun
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"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 €1,077
includes taxes & fees
9 Jun - 10 Jun
BlackBerry Private home with jacuzzi yearlong
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €448
includes taxes & fees
7 Jun - 8 Jun
American Beech in Greenport - Petite King Room 7
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"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 €585
includes taxes & fees
2 Jun - 3 Jun
Northfork Townhouse walk to all
Interior

Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
8.0 out of 10, Very good, (2 reviews)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is €727
includes taxes & fees
9 Jun - 10 Jun
Cozy beach hose minutes from Hamptons
Outdoor pool, a heated pool

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is €948
includes taxes & fees
2 Jun - 3 Jun
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"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 €656
includes taxes & fees
4 Jun - 5 Jun
Renovated Townhouse walk to all
Smart TV, fireplace, ping pong, books

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is €3,827
includes taxes & fees
9 Jun - 10 Jun
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Dining

“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”

“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”
Mattituck
9.2 out of 10, Wonderful, (5 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is €1,181
includes taxes & fees
2 Jun - 3 Jun
“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is €1,240
includes taxes & fees
8 Jun - 9 Jun
Black Swan Beachfront Home with Jacuzzi year round
On the beach, sun-loungers, beach towels

🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊

🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊
Westhampton Beach
9.4 out of 10, Exceptional, (55 reviews)
"Great house, location, pet friendly and great host!"
United States
Daniel E.
The price is €934
includes taxes & fees
8 Jun - 9 Jun
🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is €934
includes taxes & fees
2 Jun - 3 Jun
Beachfront Greenport Villa
Outdoor pool, a heated pool

Hamptons Tiana Bay Oasis

Hamptons Tiana Bay Oasis
Hampton Bays
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed this newly renovated home and had a wonderful time. Beautiful pool and grounds. "
United States
Anonymous traveller
The price is €1,182
includes taxes & fees
15 Jun - 16 Jun
Hamptons Tiana Bay Oasis
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is €1,663
includes taxes & fees
2 Jun - 3 Jun
Cozy 5 Bedroom With Wi-fi And Air Condition
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 Southampton Hotel Reviews

Harpoon House

Harpoon House

8/10 Good
"Very clean"
Carol 1-night trip
Posted 4 hours ago
Harpoon House

Find out more about Southampton

Southampton Holiday Homes information

Number of reviews
326
Accommodation
269 Holiday Homes
Lowest Price
€331
Highest Price
€4,964