Town of Southampton Vacation Rentals from CA $730: Short-Term Rentals for 2026

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

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Top Cities in Town of Southampton

A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Our top choices for Town of Southampton vacation rentals

A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

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

Flanders

Sherri K.

CA $438 total

includes taxes & fees

Nov 11 - Nov 12

A spacious living area with a white sofa, a white armchair, and a dining table. There is a staircase leading to an upper level.

2. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"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...

Lydia

CA $644 total

includes taxes & fees

Nov 1 - Nov 2

A modern building with large windows overlooking a beach.

3. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

CA $1,792 total

includes taxes & fees

Nov 2 - Nov 3

A compact kitchen with a dining table, chairs, a refrigerator, a stove, and a hanging light fixture.

4. Cozy Cottage by the beach - Seabreeze #1

Hampton Bays

CA $644 total

includes taxes & fees

Nov 5 - Nov 6

A hot tub with a checkered roof structure and surrounding greenery.

5. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

CA $2,449 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

6. Charming Accommodations in the Hamptons

Sag Harbor

CA $730 total

includes taxes & fees

Nov 2 - Nov 3

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

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

Southampton

Justin

CA $750 total

includes taxes & fees

Nov 1 - Nov 2

8. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hampton Bays

CA $540 total

includes taxes & fees

Nov 8 - Nov 9

A cozy room with a white sofa, a small table, and a window with blinds.

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

Westhampton Beach

Matt S.

CA $690 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

10. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

CA $763 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

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

Bridgehampton

Katie B.

CA $821 total

includes taxes & fees

Nov 8 - Nov 9

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

12. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

CA $1,461 total

includes taxes & fees

Nov 1 - Nov 2

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Sag Harbor

maria m.

CA $1,503 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a sofa, armchairs, a coffee table, and a TV.

14. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

CA $1,620 total

includes taxes & fees

Nov 2 - Nov 3

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...

Southampton

Melissa

CA $3,877 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

16. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

CA $2,044 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a stone fireplace, two sofas, a coffee table, and a chandelier.

17. Elegant 5-Bedroom Hamptons Home with Private Pool

Hampton Bays

Judith M.

CA $2,392 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a grey sofa, round coffee table, and a white fireplace.

18. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

Westhampton Beach

Matthew M.

CA $3,868 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

19. Cozy Hamptons Escape 3BR Minutes From Beach!

Hampton Bays

Taylor H.

CA $2,080 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with a round table and chairs, surrounded by bookshelves filled with books and decorative items.

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

Southampton

Sarah

CA $3,826 total

includes taxes & fees

Nov 1 - Nov 2

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Top Town of Southampton Hotel Reviews

The Atlantic Hotel

10/10 Excellent

"I traveled several hours and arrived early the young lady at the front desk was extremely helpful and got me in a room immediately. I was able to shower and dress before my event. Hotel was clean and very comfortable I slept well. I will definitely stay here again."

Canoe Place Inn and Cottages

10/10 Excellent

"From the moment we drove up, we were blown over by the staff, the decor, the amenities. We had a beautiful suite; I would like to hire the interior design firm. Loved the colors, the fabrics, the furniture, all the little nooks and crannies that most hotels simply don’t have. Please know that the tiny extra touches made all the difference. Excellence all the way around."

Hampton's Vacation Inn

8/10 Good

"We stayed in the two bedroom cottage. The space was very clean and organized nicely but the furniture in the living area was a little out dated and the kitchen area could use some upgrades. Also there was no TV in the bedroom which was a bummer. I found the staff to be lovely and responsive. Might want to consider adding a workout facility in the future for those who come up for the big marathon weekend or offer free passes to the local gym. Expected a little more luxury for close to $400 dollars a night. Minus and a list of local restaurants and shops would be a bonus. Close to everything and served its purpose. Would definitely stay again with some upgrades. We liked how it was private and tucked away."

Find out more about Town of Southampton

Everything you need to know about Town of Southampton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Southampton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Southampton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Town of Southampton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Southampton. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Town of Southampton vacation rentals we have selected for you start as low as CA $730 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Southampton rentals

At Expedia, we put the best Town of Southampton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Town of Southampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Southampton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Southampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Town of Southampton Vacation Rentals

Change your mind

Treat yourself

Be picky

Top Cities in Town of Southampton

Sag Harbor

Our top choices for Town of Southampton vacation rentals

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

2. Steps to the beach | Seabreeze Cottage #3

3. Beachfront Jacuzzi All Year - Black Swan Home

4. Cozy Cottage by the beach - Seabreeze #1

5. Jacuzzi year-round - Villa Luz Private Home

6. Charming Accommodations in the Hamptons

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

8. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

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

10. Immaculate Waterfront 2 bedroom!

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

12. Minutes from the beach, brand new 4 bedroom

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

14. Minutes from the beach, brand new 3 bedroom

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

16. Newly Renovated Pristine Southampton Colonial

17. Elegant 5-Bedroom Hamptons Home with Private Pool

18. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

19. Cozy Hamptons Escape 3BR Minutes From Beach!

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

Find vacation rentals that suit your style

Top Town of Southampton Hotel Reviews

The Atlantic Hotel

Find out more about Town of Southampton