Holiday Rentals Town of Southold Town from £227: Find Short-Term Rentals & Holiday Accommodations

A white colonial-style house with a green roof and a lighthouse tower.

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Town of Southold Town Accommodation: Most Popular Cities to Stay

A calm lake with a forest in the background during sunset.

Our top choices for Town of Southold Town holiday rentals

1. Cliffside Resort Condominiums

Greenport

Christine

includes taxes & fees

25 Oct - 26 Oct

A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

Greenport

Harold

includes taxes & fees

26 Oct - 27 Oct

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

3. The SandPiper

Pipes Cove

Julian V.

includes taxes & fees

18 Oct - 19 Oct

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

4. Beach Block Hideaway

Pipes Cove

Teresa C.

includes taxes & fees

4 Oct - 5 Oct

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

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

Pipes Cove

Callie E.

includes taxes & fees

28 Sept - 29 Sept

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

6. Beachfront Greenport Villa

Greenport

Kate R.

includes taxes & fees

20 Oct - 21 Oct

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

7. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

includes taxes & fees

4 Oct - 5 Oct

A restaurant with wicker furniture and large windows overlooking the ocean at sunset.

8. North Fork Fall Escape - Vineyards visits - Wineries • Apple Picking • Greenport

Mattituck

Glenn F.

includes taxes & fees

24 Oct - 25 Oct

A beach with people relaxing on chairs and sunbathing.

9. Harbor Heights

Pipes Cove

Steven R.

includes taxes & fees

5 Oct - 6 Oct

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

10. Northfork Townhouse walk to all

Greenport

Beth R.

includes taxes & fees

26 Oct - 27 Oct

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

11. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

includes taxes & fees

6 Oct - 7 Oct

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.

12. Renovated Townhouse walk to all

Greenport

Melissa A.

includes taxes & fees

20 Oct - 21 Oct

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

13. Aqua Vista

Pipes Cove

Kerri L.

includes taxes & fees

7 Oct - 8 Oct

An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

14. American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

includes taxes & fees

1 Oct - 2 Oct

A spacious hallway with high ceilings, arched columns, and chandeliers.

15. Montauk Manor

Montauk

Maria

includes taxes & fees

12 Oct - 13 Oct

16. Driftwood Resort

Montauk

William

includes taxes & fees

4 Oct - 5 Oct

17. Windward Shores Ocean Resort

Napeague

Gaurang J

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

18. Adorable Cottage, 5 min walk to water & town

Westbrook Center

Donovan V.

includes taxes & fees

28 Sept - 29 Sept

A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

19. Elegant 5-Bedroom Hamptons Home with Private Pool

Hampton Bays

Sarah A.

includes taxes & fees

29 Sept - 30 Sept

A living room with a dark grey sofa, two wooden chairs, a small table with a tray, and a large window with a view of the sea.

20. Direct waterfront renovated cottage.

Madison Center

Russell A.

includes taxes & fees

28 Sept - 29 Sept

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Top Town of Southold Town Hotel Reviews

Zey Hotel

8/10 Good

"We got off the Orient Point ferry late in evening and were welcomed so warmly by the host! Its like stepping back to a lovely time with the cozy living room on 2 floors and elegant furnishings. The complimentary coffee and lemon water. We loved the cozy feel of the living room that we just picked up muffins from a bakery and ate them with the coffee there. The ONLY reason we gave 4 stars, not 5 is the room had no sound barrier abd we heard next door t.v. on til almost midnight. We loved our stay other than that.0"

Cliffside Resort Condominiums

10/10 Excellent

"We had a great stay - the condo was just right for a family of four, comfortable and with beautiful views. The private beach was lovely for a short walk. While the walls were a little thin and we could hear noise from the neighbors on the balcony beside our bedroom one night, it’s to be expected in close quarters and everyone was quiet by 11:30. Check in was easy and location was great for many area attractions. We hope to return!"

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

10/10 Excellent

"This property is conveniently located to downtown Greenport and Mitchell Park. There are restaurants and shops within walking distance. The property itself is comfortable, with a cabana available on the property that is quite spacious."

Find out more about Town of Southold Town

Holiday Apartments in Town of Southold Town

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Change your mind

Treat yourself

Be picky

Town of Southold Town Accommodation: Most Popular Cities to Stay

Southold

Our top choices for Town of Southold Town holiday rentals

1. Cliffside Resort Condominiums

2. North Fork Resort

3. The SandPiper

4. Beach Block Hideaway

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

6. Beachfront Greenport Villa

7. American Beech in Greenport - Petite King Room 7

8. North Fork Fall Escape - Vineyards visits - Wineries • Apple Picking • Greenport

9. Harbor Heights

10. Northfork Townhouse walk to all

11. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

12. Renovated Townhouse walk to all

13. Aqua Vista

14. American Beech in Greenport - Deluxe King 6

15. Montauk Manor

16. Driftwood Resort

17. Windward Shores Ocean Resort

18. Adorable Cottage, 5 min walk to water & town

19. Elegant 5-Bedroom Hamptons Home with Private Pool

20. Direct waterfront renovated cottage.

Find holiday rentals that suit your style

Top Town of Southold Town Hotel Reviews

Zey Hotel

Find out more about Town of Southold Town

Holiday Apartments in Town of Southold Town

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