Southold, NY Vacation Homes from AED 348

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Our top choices for Southold vacation homes

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

1. The SandPiper

Pipes Cove

Manuela C.

AED 848 total

includes taxes & fees

30 Nov - 1 Dec

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

2. Aqua Vista

Pipes Cove

Kerri L.

AED 890 total

includes taxes & fees

9 Nov - 10 Nov

A beach with people relaxing, a pier extending into the water, and a clear sky.

3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

AED 1,278 total

includes taxes & fees

9 Nov - 10 Nov

A wooden pathway leading to a beach with scattered rocks and greenery.

4. Beach Block Hideaway

Pipes Cove

Teresa C.

AED 1,574 total

includes taxes & fees

18 Nov - 19 Nov

An outdoor dining area with hanging lights, palm trees, and a bar.

5. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

AED 1,066 total

includes taxes & fees

18 Nov - 19 Nov

A modern dining area with a wooden table, white chairs, and a chandelier.

6. Northfork Townhouse walk to all

Greenport

Beth R.

AED 2,092 total

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

7. Beachfront Greenport Villa

Greenport

Kate R.

AED 3,294 total

includes taxes & fees

18 Nov - 19 Nov

A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

8. Renovated Townhouse walk to all

Greenport

Liz H.

AED 1,966 total

includes taxes & fees

1 Dec - 2 Dec

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

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

Southampton

Justin

Vaulted living room with statement chandelier and cozy sectional

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

Sag Harbor

maria m.

AED 3,800 total

includes taxes & fees

9 Nov - 10 Nov

A dining area with a round table, six chairs, and a chandelier.

11. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

AED 5,080 total

includes taxes & fees

9 Nov - 10 Nov

A room with a black sofa with a checkered cushion, a white shelf with towels, and a window with blue blinds.

12. American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

AED 1,204 total

includes taxes & fees

9 Nov - 10 Nov

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

13. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

AED 6,046 total

includes taxes & fees

9 Nov - 10 Nov

A wooden interior with a staircase, a blue sofa, and a fireplace.

14. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Mattituck

Frank T.

AED 4,799 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Bridgehampton

Katie B.

AED 1,956 total

includes taxes & fees

8 Nov - 9 Nov

A modern building with large windows overlooking a beach.

16. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

John M.

AED 4,710 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Southampton

Melissa

AED 9,716 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

18. Lovely & Spacious Sag Harbor escape with heated pool

Sag Harbor

AED 7,768 total

includes taxes & fees

9 Nov - 10 Nov

A cozy living room with a sofa, a coffee table, and a dining area with chairs.

19. NEW private studio 1.1 miles to beach in East Lyme

East Lyme

AED 500 total

includes taxes & fees

9 Nov - 10 Nov

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

20. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

AED 3,873 total

includes taxes & fees

5 Nov - 6 Nov

View all properties

Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

See all hotels in Southold

A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top reviews in Southold

A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.

Silver Sands Motel & Beach Bungalows

Greenport

10/10 Excellent

Nicole

A two-story house with a balcony, outdoor seating area, and a variety of plants.

Zey Hotel

Greenport

10/10 Excellent

Jennifer

The Harbor Front Inn

Greenport

10/10 Excellent

Maureen

A spacious room with wicker furniture, large windows, and a view of the sea.

Sound View Greenport

Greenport

10/10 Excellent

Marilyn

A serene landscape with a calm body of water reflecting trees with autumn foliage.

House on Chase Creek

The Heights

10/10 Excellent

Damon

A balcony with a view of the ocean, a lawn, and a house in the background.

Cliffside Resort Condominiums

Greenport

10/10 Excellent

Jeannine

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

The Menhaden

Greenport

10/10 Excellent

Anonymous traveler

A waterfront property with a large house, multiple boats docked, and lush greenery.

Sag Harbor Inn

Sag Harbor

10/10 Excellent

Anonymous traveler

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

The Bentley Hotel Southampton

Southampton

10/10 Excellent

Jennifer

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

The Hampton Maid

Hampton Bays

10/10 Excellent

Such a beautiful property, lots of trees, lovely landscaping. They keep Crassula in pots on all of the porches as long as weather permits. The room I stayed in (double queen) was very spacious. Wood beamed ceiling with a ceiling fan, walk in shower. Loved the restaurant that was open for breakfast daily. Open for dinner Tuesday - Saturday while I was there. It's still family owned and run after 69 years. Great dining options all around, and lots to see and do on the island - although you...

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