Holiday Homes in Town of Southampton

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Top Cities in Town of Southampton

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Riverhead

Riverhead
Ponquogue Beach
Holiday HomesHoliday Homes

Hampton Bays

Hampton Bays

Featured Holiday Homes in Town of Southampton

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

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

10.0 out of 10, Exceptional, (10)
"Great property for two people right next to the downtown. Our stay was comfortable and clean!"
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Hamptons Retreat
Terrace/patio

Hamptons Retreat

Hamptons Retreat
Southampton Newly-renovated Home / Heated Pool!
A heated pool

Southampton Newly-renovated Home / Heated Pool!

10.0 out of 10, Exceptional, (29)
"We’ll kept - great layout, great backyard would love to go bakc"
Southampton Newly-renovated Home / Heated Pool!
Private completely fenced in property. Near beach
Terrace/patio

Private completely fenced in property. Near beach

9.6 out of 10, Exceptional, (22)
"The place is in nice neighborhood and private entrance. It has all the amenities for a good staying. Definitely will stay again in the future."
The price is AU$2,933
includes taxes & fees
2 Sept - 3 Sept
Private completely fenced in property. Near beach
Luxury Beach House, Heated Pool, Dune Rd beaches, pets yes
Outdoor pool, a heated pool

Luxury Beach House, Heated Pool, Dune Rd beaches, pets yes

10.0 out of 10, Exceptional, (11)
"An absolute perfect home for a family looking to enjoy"
Luxury Beach House, Heated Pool, Dune Rd beaches, pets yes
Relax in Hampton Bays...
Sun-loungers, beach towels

Relax in Hampton Bays...

9.8 out of 10, Exceptional, (72)
"We had a wonderful weekend at this lovely home near the bay. The house was beautifully maintained and thoughtfully equipped with everything we needed — we especially loved the great outdoor shower. The surrounding area was great for biking, and we played pickleball at Red Creek Park just three miles away — eight courts and it was empty when we went at noon. Both the nearby ocean beach and Roger’s Beach in Westhampton were convenient and beautiful. The location is close to Quogue and Westhampton....
Relax in Hampton Bays...
2 Bedroom Hamptons Waterfront Cottage Rental
Outdoor dining

2 Bedroom Hamptons Waterfront Cottage Rental

10.0 out of 10, Exceptional, (13)
"Renovated cabin on the Great Peconic Bay, couldn’t ask for a better setting."
2 Bedroom Hamptons Waterfront Cottage Rental
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (11)
"Great place! Great communication with property owner!"
The price is AU$972
includes taxes & fees
5 Aug - 6 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (184)
"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

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

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Charming Village home in the heart of Southampton
Smart TV

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (22)
"Great location, clean, easy checkin, slept 7 comfortably"
Charming Village home in the heart of Southampton
Spacious & Newly Renovated Hamptons Home with Movie Theater, Pool, Gameroom, Gym
Terrace/patio

Spacious & Newly Renovated Hamptons Home with Movie Theater, Pool, Gameroom, Gym

10.0 out of 10, Exceptional, (1)
"Truly couldn’t recommend The Benchmark enough! The house was clean and beautiful, with every detail carefully thought out to help maximize our stay. The pool/backyard was the best part and really made our stay. The entire house is very spacious and perfect for large groups! "
Spacious & Newly Renovated Hamptons Home with Movie Theater, Pool, Gameroom, Gym
Westhampton Beach Town and Country
Outdoor spa tub

Westhampton Beach Town and Country

9.8 out of 10, Exceptional, (37)
"Outdoor space was wonderful. The house was well stocked with supplies."
Westhampton Beach Town and Country
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
A heated pool

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

10.0 out of 10, Exceptional, (32)
"This home fit everyone perfectly. The great room was a stunner and the bay views awesome! "
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Smart TV, fireplace, computer monitors, printers

5 Bedrooms! 4 Min to the Beach! HEATED POOL!

10.0 out of 10, Exceptional, (1)
"Communication with the property manager was an A. Highly recommend this home! "
The price is AU$4,368
includes taxes & fees
18 Aug - 19 Aug
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool

Gorgeous private Hamptons house with pool and volleyball court

7.8 out of 10, Good, (22)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court
Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.
Terrace/patio

Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.

9.8 out of 10, Exceptional, (59)
"House was very clean! Owner was attentive. Highly recommend for a family vacation! Kids were never bored! "
Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.
The Sandbox! Completely renovated in-town 3br, 2+ bath with pool & poolhouse.
Pool

The Sandbox! Completely renovated in-town 3br, 2+ bath with pool & poolhouse.

2.0 star property
10.0 out of 10, Exceptional, (1)
"My family just returned from a beautiful weekend in Bridgehampton. We go every year to celebrate my mom's birthday, and this may be the best rental we've ever had! Dan was friendly and very responsive, and the listing was better than described! It was a perfect space for my family and my mom- clean, new, bright and everything you would need to have a lovely stay. It would be even more fabulous in summer, given the beautiful pool, poolhouse and outdoor shower we did not use because of the time of...
The Sandbox! Completely renovated in-town 3br, 2+ bath with pool & poolhouse.
Cove View Manor of Sag Harbor
A heated pool

Cove View Manor of Sag Harbor

10.0 out of 10, Exceptional, (70)
"Wonderful time will be coming back next year for 3 years in a row"
Cove View Manor of Sag Harbor
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (68)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
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 Town of Southampton Hotel Reviews

The Hampton Maid

The Hampton Maid

10/10 Excellent
"This property was amazing! I took my wife here recently for her birthday. The property was immaculate our room was inside the WINDMILL. We ate at the restaurant R’Aire amazing food and Chef was very hospitable, welcoming, just really down to earth warm person. We, will definitely make this place a destination location on a regular bases. "
Reginald 2-night trip
Posted 2 days ago
The Hampton Maid