Town of Southampton Holiday Rentals: Short-Term Accommodations for Rent

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

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Our top choices for Town of Southampton holiday rentals

A beach with footprints leading to the water, a sunset in the background, and a clear sky.

1. 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

HK$3,395 total

includes taxes & fees

11 Oct - 12 Oct

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,

Flanders

James W.

HK$2,502 total

includes taxes & fees

12 Oct - 13 Oct

A modern building with large windows overlooking a beach.

3. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

HK$9,679 total

includes taxes & fees

13 Oct - 14 Oct

A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

4. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

HK$13,074 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Southampton

Justin

HK$4,689 total

includes taxes & fees

11 Oct - 12 Oct

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

HK$3,972 total

includes taxes & fees

12 Oct - 13 Oct

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

7. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

HK$4,510 total

includes taxes & fees

11 Oct - 12 Oct

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

Westhampton Beach

Chris J.

HK$5,891 total

includes taxes & fees

19 Oct - 20 Oct

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

Robert R.

HK$4,609 total

includes taxes & fees

1 Nov - 2 Nov

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

10. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

HK$8,401 total

includes taxes & fees

12 Oct - 13 Oct

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

11. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

HK$8,894 total

includes taxes & fees

2 Nov - 3 Nov

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

Hampton Bays

Judith M.

HK$7,684 total

includes taxes & fees

12 Oct - 13 Oct

A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

13. Amazing Southampton Home with Private Heated Pool

Southampton

Serina R.

HK$10,718 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Sag Harbor

maria m.

HK$8,742 total

includes taxes & fees

12 Oct - 13 Oct

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

15. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

Westhampton Beach

Matthew M.

HK$21,285 total

includes taxes & fees

13 Oct - 14 Oct

A wooden house with a front porch, white railings, and a double door.

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

Southampton

Melissa

HK$22,677 total

includes taxes & fees

11 Oct - 12 Oct

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!

Hampton Bays

Taylor H.

HK$12,292 total

includes taxes & fees

11 Oct - 12 Oct

18. VACATION HOME ON THE BAY

Hampton Bays

A wooden gate partially covered by lush green ivy.

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

Southampton

Deborah V.

HK$22,662 total

includes taxes & fees

12 Oct - 13 Oct

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

20. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

HK$22,123 total

includes taxes & fees

11 Oct - 12 Oct

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Top Town of Southampton Hotel Reviews

Canoe Place Inn and Cottages

10/10 Excellent

"Fantastic venue. Excellent service. Old school. Loved it"

Faraway Sag Harbor

10/10 Excellent

"We were pleased with the excellent location to Sag Harbor's Main Street and the Zagaya restaurant *upstairs. It was superb! The staff was very friendly and helpful. The rooms were small and the baths particularly small so just a heads up on that although the toiletries were really nice. The hotel has a great vibe at night with live music in the bar area on Thursday evenings. The weather was cool...absolutely gorgeous for early October so we didn't use the pool/cabanas (although it was heated). I did peek in the fitness room and it was very nice. Not enough time to check out the spa but there's always next time!"

Seven Beach Lane

10/10 Excellent

"My stay was absolutely incredible! From the moment I arrived, Jen made me feel so welcome. After an early travel day, her warmth and kindness immediately made me feel comfortable and at home. She gave me so many great recommendations and was incredibly attentive, making everything over the last two days feel completely seamless and enjoyable. As a solo traveler, I also felt incredibly safe on the property, which was so important to me. The location is amazing and within easy walking distance of town, and the property itself is extremely clean, modern, and beautiful. I absolutely loved the sauna and cold plunge, and I already can’t wait to come back. I would 100% recommend staying here to anyone visiting the area. Such a wonderful experience from beginning to end!"

Hampton Bays Hotel on Main

10/10 Excellent

"This hotel was clean, comfy and reasonably priced. Everything worked out well virtually checking in and was perfect for our one night stay. Parking was a little nerve racking since there was no parking on the premise but the street parking worked out well reading the street signs and moving the car when necessary."

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Town of Southampton holiday rentals

1. Steps to the beach | Seabreeze Cottage #3

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

3. Beachfront Jacuzzi All Year - Black Swan Home

4. Jacuzzi year-round - Villa Luz Private Home

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

6. Charming Accommodations in the Hamptons

7. Immaculate Waterfront 2 bedroom!

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

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

10. Minutes from the beach, brand new 4 bedroom

11. Minutes from the beach, brand new 3 bedroom

12. Elegant 5-Bedroom Hamptons Home with Private Pool

13. Amazing Southampton Home with Private Heated Pool

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

15. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

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

17. Cozy Hamptons Escape 3BR Minutes From Beach!

18. VACATION HOME ON THE BAY

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

20. Newly Renovated Pristine Southampton Colonial

Find holiday rentals that suit your style

Top Town of Southampton Hotel Reviews

Canoe Place Inn and Cottages

Hamlet Inn

Faraway Sag Harbor

Seven Beach Lane

Hampton Bays Hotel on Main

Southampton Inn

Budget Host East End

Topping Rose House

Ocean View Terrace Inn