Holiday Rentals in Town of Southampton
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Featured Town of Southampton Holiday Rentals

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property

Bridgehampton

9.6 out of 10, Exceptional, (15)

9.6/10

Exceptional

(15)

"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "

James S.

The price is HK$1,231

HK$1,231

HK$2,977 total

includes taxes & fees

27 Oct - 28 Oct

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

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

Westhampton Beach

10.0 out of 10, Exceptional, (192)

10/10

Exceptional

(192)

"House was more then I can imagine , host was great , house literally have anything you forgot at home . "

Isiah L.

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

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

Hampton Bays

9.6 out of 10, Exceptional, (140)

9.6/10

Exceptional

(140)

"Perfect property to hangout and stay entertained for hours"

Ryder I.

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

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

Southampton

9.8 out of 10, Exceptional, (32)

9.8/10

Exceptional

(32)

"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."

Patricia Fox M.

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

Relax in Hampton Bays...

Hampton Bays

9.8 out of 10, Exceptional, (76)

9.8/10

Exceptional

(76)

"We stayed for a weekend while out east for a wedding. The property was lovely and exactly as pictured."

Jennifer P.

Relax in Hampton Bays...

1 bedroom, iron/ironing board, free WiFi, bed sheets

Fairy Tale Guest Cottage in Magic Garden by Pool

Bridgehampton

10.0 out of 10, Exceptional, (76)

10/10

Exceptional

(76)

"It was a beautiful cottage on a gorgeous property with gracious hosts. I recommend it!!!!"

Lisa

Fairy Tale Guest Cottage in Magic Garden by Pool

Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

Westhampton Beach

10.0 out of 10, Exceptional, (91)

10/10

Exceptional

(91)

"The house was exactly as described, with lots of space and fully stocked. The pool was amazing. The location was perfect and within walking distance of Westhampton Beach. Colleen was an excellent host and extremely communicative throughout our stay. Highly recommend :)"

Max S.

Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

6 bedrooms, iron/ironing board, Internet, bed sheets

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

Southampton

9.8 out of 10, Exceptional, (17)

9.8/10

Exceptional

(17)

"Had an amazing stay here and would definitely recommend to others!! Only issue was the heat did not work in certain areas. House and backyard / pool area was spacious and beautiful. Perfect for large groups. Would definitely stay again."

shelby h.

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

Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

Southampton

9.6 out of 10, Exceptional, (7)

9.6/10

Exceptional

(7)

"Loved it! "

debra sue k.

Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

3 bedrooms, in-room safe, iron/ironing board, free WiFi

Canoe Place Waterfront Residences

4.0 star property

Hampton Bays

10.0 out of 10, Exceptional, (1)

10/10

Exceptional

(1)

Canoe Place Waterfront Residences

Smart TV, fireplace, DVD player, table football

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor

10.0 out of 10, Exceptional, (89)

10/10

Exceptional

(89)

"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"

Kilee B.

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

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

Hampton Bays

9.4 out of 10, Exceptional, (73)

9.4/10

Exceptional

(73)

"As always everything was excellent, This is our third stay at this property and we are booked for 2026"

Michael R.

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

Private Bridgehampton home with Pool.

Sag Harbor

10.0 out of 10, Exceptional, (4)

10/10

Exceptional

(4)

"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!"

Heather M.

Private Bridgehampton home with Pool.

Microwave, oven, stovetop, coffee/tea maker

Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...

Sag Harbor

9.0 out of 10, Wonderful, (2)

9.0/10

Wonderful

(2)

"Great location and comfortable stay, amazing sheets.Ended up buying for my home. "

David Y.

Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...

Summer getaway

East Quogue

9.0 out of 10, Wonderful, (14)

9.0/10

Wonderful

(14)

"Perfect location for a family holiday "

Olaf U.

Summer getaway

3 bedrooms, iron/ironing board, WiFi, bed sheets

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Hampton Bays

9.8 out of 10, Exceptional, (18)

9.8/10

Exceptional

(18)

"We had a wonderful stay here with our family. Great location, right on the beach, looking forward to returning!"

Kyle D.

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

7 bedrooms, iron/ironing board, travel cot, free WiFi

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Southampton

9.8 out of 10, Exceptional, (54)

9.8/10

Exceptional

(54)

"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."

Mary B.

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Minutes from the beach, brand new 4 bedroom

Southampton

10.0 out of 10, Exceptional, (3)

10/10

Exceptional

(3)

"perfect for families"

Okito H.

The price is HK$3,496

HK$3,496

HK$8,512 total

includes taxes & fees

21 Oct - 22 Oct

Minutes from the beach, brand new 4 bedroom

Chic Southampton Getaway with Heated Pool & Seamless Indoor-Outdoor Living

Southampton

10.0 out of 10, Exceptional, (1)

10/10

Exceptional

(1)

"Great"

Sophia C.

Chic Southampton Getaway with Heated Pool & Seamless Indoor-Outdoor Living

5 bedrooms, desk, iron/ironing board, travel cot

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

Westhampton Beach

10.0 out of 10, Exceptional, (101)

10/10

Exceptional

(101)

"Peaceful and lovely home. Our family of 4 including 2 teens enjoyed the pool and outdoor area. The gameroom was a bonus. Plenty of space, great kitchen and the living room has seating for everyone. Extremely clean with all the amenities. "

Courtney K.

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers 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 Town of Southampton Hotel Reviews

The Bentley Hotel Southampton

10/10 Excellent

"It was very spacious!"

Donna 1-night trip

Posted 2 days ago

The Bentley Hotel Southampton

Hampton Bays Hotel on Main

10/10 Excellent

"Loved the 2 bar options on the property."

Jennifer 1-night trip

Posted 3 days ago

Hampton Bays Hotel on Main

Hampton's Vacation Inn

10/10 Excellent

"Lovely property. Convenient location. Will stay again. "

Camille 2-night trip

Posted 4 days ago

Hampton's Vacation Inn

Hamlet Inn

10/10 Excellent

"This was the perfect place to stay right down the street from Stony Brook University. We like that this hotel was small and we parked right outside of our room. Everything was clean and neatly organized. Plenty of towels and toiletries. It was the perfect hotel for one night so that I didn't have to drive to my conference at SBU in the morning. It would be a nice place for a weekend as well. The staff was very pleasant and welcoming. "

Madeline 1-night trip

Posted 6 days ago

Hamlet Inn

The Atlantic Hotel

10/10 Excellent

"Great stay overall. Only suggestion would be to put a light on the side of the building. "

Christopher 2-night trip

Posted 6 days ago

The Atlantic Hotel

Bayview Resort

10/10 Excellent

"We love this place. We immediately felt home. Accommodating and helpful. What else can we ask for. :) Though Expedia should do better as a 3rd party by communicating to customers specific conditions and amenities. We are so lucky that Bayview Resort help us a lot. :) Grateful that this weekend was restful and safe. "

April 2-night trip

Posted 7 days ago

Bayview Resort

Southampton Inn

10/10 Excellent

"Such a great location!"

Elizabeth 1-night trip

Posted 8 days ago

Southampton Inn

The Hampton Maid

10/10 Excellent

"Property was very welcoming thanx for having me"

Jemaine 2-night trip

Posted 10 days ago

The Hampton Maid

A Room At The Beach

10/10 Excellent

"Stylish, greets walkable location, loved the grounds and the snacks and wine "

Karin 1-night trip

Posted 2 weeks ago

A Room At The Beach

Unlock instant savings with Member Prices

Town of Southampton Holiday Rentals

Change your mind

Treat yourself

Be picky

Featured Town of Southampton Holiday Rentals

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

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

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

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

Relax in Hampton Bays...

Fairy Tale Guest Cottage in Magic Garden by Pool

Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

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

Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

Canoe Place Waterfront Residences

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

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

Private Bridgehampton home with Pool.

Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...

Summer getaway

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Minutes from the beach, brand new 4 bedroom

Chic Southampton Getaway with Heated Pool & Seamless Indoor-Outdoor Living

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

Top Town of Southampton Hotel Reviews

The Bentley Hotel Southampton