A man carrying a woman in front of a pool with two American flags, surrounded by greenery and a monument.

Town of Southampton Holiday Rentals

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Our top choices for Town of Southampton holiday rentals

A spacious living room with a large sofa, a round coffee table, and a television. A kitchen with a refrigerator and cabinets is visible in the background.

1. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is HK$675
HK$3,648 total
includes taxes & fees
13 Oct - 14 Oct
Steps to the beach | Seabreeze Cottage #3
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

2. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is HK$1,130
HK$2,501 total
includes taxes & fees
6 Oct - 7 Oct
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

3. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is HK$879
HK$13,170 total
includes taxes & fees
5 Oct - 6 Oct
Jacuzzi year-round - Villa Luz Private Home
A modern building with large windows overlooking a beach.

4. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is HK$1,106
HK$9,678 total
includes taxes & fees
4 Oct - 5 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

5. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is HK$1,765
HK$3,971 total
includes taxes & fees
27 Oct - 28 Oct
Charming Accommodations in the Hamptons
Roger’s Beach

6. Prime location, walk to all, cozy cottage Westhampton Beach

Prime location, walk to all, cozy cottage Westhampton Beach
Westhampton Beach
10.0 out of 10, Exceptional, (3 reviews)
"Erica was very communicative and helpful. Very cozy with a great location."
United States
Chris J.
The price is HK$3,139
HK$5,639 total
includes taxes & fees
19 Oct - 20 Oct
Prime location, walk to all, cozy cottage Westhampton Beach
A covered patio with a table and chairs, large windows, and a view of greenery.

7. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (10 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
The price is HK$2,746
HK$4,608 total
includes taxes & fees
4 Oct - 5 Oct
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

8. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is HK$2,118
HK$4,509 total
includes taxes & fees
13 Oct - 14 Oct
Immaculate Waterfront 2 bedroom!
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

9. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is HK$2,354
HK$4,769 total
includes taxes & fees
1 Nov - 2 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

10. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is HK$3,531
HK$7,494 total
includes taxes & fees
21 Oct - 22 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

11. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is HK$3,531
HK$8,704 total
includes taxes & fees
6 Oct - 7 Oct
Minutes from the beach, brand new 4 bedroom
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

12. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is HK$3,531
HK$7,566 total
includes taxes & fees
13 Oct - 14 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is HK$4,449
HK$8,741 total
includes taxes & fees
2 Oct - 3 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern living room with a grey sofa, round coffee table, and a white fireplace.

14. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (6 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is HK$13,151
HK$21,721 total
includes taxes & fees
4 Oct - 5 Oct
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A wooden house with a front porch, white railings, and a double door.

15. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is HK$16,774
HK$22,673 total
includes taxes & fees
13 Oct - 14 Oct
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

16. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is HK$6,897
HK$12,949 total
includes taxes & fees
26 Oct - 27 Oct
Amazing Southampton Home with Private Heated Pool
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

17. Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (7 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is HK$9,415
HK$12,021 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Hamptons Escape 3BR Minutes From Beach!
A wooden gate partially covered by lush green ivy.

18. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (16 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is HK$16,740
HK$22,031 total
includes taxes & fees
1 Nov - 2 Nov
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

19. Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is HK$15,811
HK$23,496 total
includes taxes & fees
3 Oct - 4 Oct
Newly Renovated Pristine Southampton Colonial
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

20. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is HK$12,005
HK$17,463 total
includes taxes & fees
2 Oct - 3 Oct
Lovely & Spacious Sag Harbor escape with heated pool
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

Bayview Resort

Bayview Resort

8/10 Good
"Staff is amazing, very helpful and friendly. First time traveling with our dog, they were very accommodating. I just love the serenity of this place in particular in the morning hours by the water, blissful and calming. Very centrally located across all major towns."
Meltem 4-night trip
Posted 12 hours ago
Bayview Resort