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

Vacation Rentals in Town of Southampton

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Top Cities in Town of Southampton

A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.
Vacation RentalsVacation Rentals

Southampton

Southampton

Our top choices for Town of Southampton vacation 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
$406 nightly
The price is $432
Oct 5 - Oct 6
Total with taxes and fees
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.
$279 nightly
The price is $319
Oct 6 - Oct 7
Total with taxes and fees
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.
$1,584 nightly
The price is $1,679
Oct 4 - Oct 5
Total with taxes and fees
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.
$1,161 nightly
The price is $1,233
Oct 4 - Oct 5
Total with taxes and fees
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
$446 nightly
The price is $510
Oct 5 - Oct 6
Total with taxes and fees
Charming Accommodations in the Hamptons
Roger’s Beach

6. Prime location, walk to all, cozy cottage WHB

Prime location, walk to all, cozy cottage WHB
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.
$629 nightly
The price is $719
Oct 19 - Oct 20
Total with taxes and fees
Prime location, walk to all, cozy cottage WHB
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.
$514 nightly
The price is $587
Oct 4 - Oct 5
Total with taxes and fees
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.
$503 nightly
The price is $575
Oct 8 - Oct 9
Total with taxes and fees
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.
$514 nightly
The price is $587
Nov 1 - Nov 2
Total with taxes and fees
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
$836 nightly
The price is $955
Oct 21 - Oct 22
Total with taxes and fees
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.
$971 nightly
The price is $1,109
Oct 4 - Oct 5
Total with taxes and fees
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.
$857 nightly
The price is $979
Oct 4 - Oct 5
Total with taxes and fees
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.
$975 nightly
The price is $1,114
Oct 3 - Oct 4
Total with taxes and fees
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.
$2,423 nightly
The price is $2,768
Oct 4 - Oct 5
Total with taxes and fees
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
$2,570 nightly
The price is $2,921
Oct 4 - Oct 5
Total with taxes and fees
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.
$1,223 nightly
The price is $1,375
Oct 20 - Oct 21
Total with taxes and fees
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.
$1,371 nightly
The price is $1,566
Oct 3 - Oct 4
Total with taxes and fees
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.
$2,584 nightly
The price is $2,827
Nov 1 - Nov 2
Total with taxes and fees
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.
$2,621 nightly
The price is $2,995
Oct 3 - Oct 4
Total with taxes and fees
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
$1,948 nightly
The price is $2,226
Oct 3 - Oct 4
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Town of Southampton Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Kind of expected to be disappointed. However, really delighted. Room was lovely, clean and thoughtful appointments. Location was OK, but doable."
Randi 2-night trip
Posted less than an hour ago
The Bentley Hotel Southampton

Find out more about Town of Southampton

Discover your perfect Town of Southampton vacation rental with Expedia

How many vacation rentals are available in Town of Southampton?


Expedia has plenty of vacation rentals to choose from in and around  Town of Southampton, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Town of Southampton?


The selection of Town of Southampton vacation rentals we have selected for you start as low as $1,109 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Town of Southampton?


Vacation rentals in Town of Southampton come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Town of Southampton vacation rentals to suit everyone. 


Why should I choose a vacation rental in Town of Southampton?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Town of Southampton vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Town of Southampton?


Find vacation rentals in Town of Southampton by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Town of Southampton.  


What amenities are available in a vacation rental in Town of Southampton?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Town of Southampton vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Town of Southampton?   


Everytime is a great time to head to Town of Southampton! Staying in a Town of Southampton vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Town of Southampton. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Town of Southampton vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Town of Southampton, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Town of Southampton vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.