Holiday Homes in Town of Southampton

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Town of Southampton

Our top choices for Town of Southampton holiday homes

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Hampton Bays
9.6 out of 10, Exceptional, (147 reviews)
"Weekend getaway "
United States
Eric S.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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, (200 reviews)
"Great host, everything that we needed for our trip was available, ample room for the 9 of us."
United States
matthew p.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Southampton
9.8 out of 10, Exceptional, (33 reviews)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️
Southampton
10.0 out of 10, Exceptional, (109 reviews)
"Great location. "
United States
Lauren H.
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

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
10.0 out of 10, Exceptional, (16 reviews)
"Great host & location. Would stay again"
United States
Chris H.
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Hamptons Modern Retreat NEW CONS

Hamptons Modern Retreat NEW CONS
Southampton
10.0 out of 10, Exceptional, (14 reviews)
"Property was was everything and more than described!"
United States
Dennis T.
Hamptons Modern Retreat NEW CONS

Gorgeous private Hamptons house with pool and volleyball court

Gorgeous private Hamptons house with pool and volleyball court
Hampton bays
7.0 out of 10, Good, (29 reviews)
"Great location "
United States
samantha l.
Gorgeous private Hamptons house with pool and volleyball court

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Eastport
9.6 out of 10, Exceptional, (35 reviews)
"We had a amazing stay and plan to come back next July again"
United States
Gina G.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Water Mill
9.0 out of 10, Wonderful, (4 reviews)
"The property was perfect for our large group. Exactly as described and in a very convenient location with fantastic sunsets. Romita is an incredibly responsive and helpful host!"
United States
Michael S.
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Private 2.1 acre gated home with heated pool and tennis & pickleball court

Private 2.1 acre gated home with heated pool and tennis & pickleball court
Southampton
10.0 out of 10, Exceptional, (21 reviews)
"Perfect house for our stay. Had a wonderful time!"
United States
Tom C.
Private 2.1 acre gated home with heated pool and tennis & pickleball court

A Quiet Place in the Hamptons

A Quiet Place in the Hamptons
East Quogue
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic house for the extended family ! We loved the pool , enjoyed bbq grilling and hanging out together! "
United States
Anonymous traveller
A Quiet Place in the Hamptons

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger
Westhampton
9.6 out of 10, Exceptional, (110 reviews)
"Great place. We enjoyed our stay."
United States
Hitesh S.
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Westhampton Beach
10.0 out of 10, Exceptional, (101 reviews)
"Very responsive host (Esther was amazing!) and the whole family really enjoyed the property - inside and out!"
United States
Christine H.
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!

Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!
Hampton Bays
9.4 out of 10, Exceptional, (10 reviews)
"Great property with ease of access! Plenty of amenities and very kind host!"
United States
Travis A.
Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!

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

Beautifully renovated historic home in Sag Harbor Village. Walk to Everything.

Beautifully renovated historic home in Sag Harbor Village. Walk to Everything.
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"The perfect house !Great location - walk to town! "
United States
JODI S.
Beautifully renovated historic home in Sag Harbor Village. Walk to Everything.

Central Private Bridgehampton home

Central Private Bridgehampton home
Sag Harbor
10.0 out of 10, Exceptional, (4 reviews)
"The house and property were so nice. We have a 10 and 11 year old. They played outside or were swimming in the pool the entire time. It's close to great shopping and beaches. It was a very relaxing and enjoyable long weekend. Everything was perfect!"
United States
Heather M.
Central Private Bridgehampton home

10 Bedroom Hampton House with a regulation size Pickleball court

10 Bedroom Hampton House with a regulation size Pickleball court
Hampton Bays
10.0 out of 10, Exceptional, (32 reviews)
"Location of this property is impeccable."
United States
Stephen M.
10 Bedroom Hampton House with a regulation size Pickleball court

Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
west hampton beach
10.0 out of 10, Exceptional, (83 reviews)
"Perfect location and pristine beach access. The best end of summer vacation for our family of 4. "
United States
Adrianna R.
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Southampton
9.8 out of 10, Exceptional, (19 reviews)
"Beautiful home and grounds, perfect for our extended family gathering over Thanksgiving! "
United States
Charrita E.
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Town of Southampton Hotel Reviews

Find out more about Town of Southampton

Town of Southampton Holiday Homes information

Number of reviews
855
Accommodation
821 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia