Holiday Rentals Town of Southold Town from ₹12,391: Find Short-Term Rentals & Holiday Accommodations

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A pebbled beach at sunset with the sun setting over the horizon.

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Our top choices for Town of Southold Town holiday rentals

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

1. Cliffside Resort Condominiums

Greenport

William

₹31,073 total

includes taxes & fees

26 Nov - 27 Nov

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

2. North Fork Resort

Greenport

Altynai

₹33,141 total

includes taxes & fees

15 Nov - 16 Nov

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

3. Montauk Manor

Montauk

barbara

₹16,732 total

includes taxes & fees

30 Nov - 1 Dec

4. Windward Shores Ocean Resort

Napeague

Banessa

₹16,713 total

includes taxes & fees

15 Nov - 16 Nov

5. Montauk Oceanside Suites

Downtown Montauk

Mitchell

₹15,643 total

includes taxes & fees

15 Nov - 16 Nov

6. The Surf Club

Montauk

na

A modern living room with a sofa, a coffee table, and a view of the outdoors through large glass doors.

7. Offshore Spa & Residences

Downtown Montauk

"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...

Frank

₹32,848 total

includes taxes & fees

15 Dec - 16 Dec

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

8. Groton Home < 1 Mi to Beach on Long Island Sound!

Groton

₹75,960 total

includes taxes & fees

22 Nov - 23 Nov

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Top Town of Southold Town Hotel Reviews

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

James

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.

Home2 Suites by Hilton East Haven New Haven

The Centre

10/10 Excellent

Chris

A blue door, a small table with a potted plant, and a green chair on a porch.

Marina Bay Cottages

Waterford

10/10 Excellent

Lorna

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

The Shoals Suites and Slips

Southold

10/10 Excellent

Paul

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

We had a lovely 3 night stay at this beautiful traditional family owned property (2 rooms/cabins). It was a perfect reset after 5 nights spent in NYC, the surroundings were so peaceful and well maintained as were the rooms. Great to see some local wildlife on the grounds at times too. Staff were friendly and helpful, parking is conveniently located beside each room, making it easy for luggage etc. Daily maid service, rooms were immaculately clean. We had breakfast at the property on one of the...

Sharon

A restaurant with wooden beams, large windows, and blue chairs. Tables are set with wine glasses and cutlery.

The Whaler's Inn

Mystic

10/10 Excellent

This hotel has one of the best, if not the best, sites in Mystic. Our room had a great view of the river and swing bridge. Whilst there's no elevator and we were on the top floor help with our baggage on arrival and departure were readily and quickly available. Room was clean and comfortable and the bed provided a great night's sleep. Only slight let down was the included "continental" breakfast. But if you want a more varied or larger meal there are plenty of places nearby. Recommended.

David

A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.

Hotel Marcel New Haven, Tapestry Collection By Hilton

Long Wharf

10/10 Excellent

Iain

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

Top cities in Town of Southold Town

Greenport

Check prices for these dates

Our top choices for Town of Southold Town holiday rentals

1. Cliffside Resort Condominiums

2. North Fork Resort

3. Montauk Manor

4. Windward Shores Ocean Resort

5. Montauk Oceanside Suites

6. The Surf Club

7. Offshore Spa & Residences

8. Groton Home < 1 Mi to Beach on Long Island Sound!

Find holiday rentals that suit your style

Top Town of Southold Town Hotel Reviews

The Bentley Hotel Southampton

10/10 Excellent

Find out more about Town of Southold Town

Holiday Apartments in Town of Southold Town