Southold Vacation Rentals, Homes, & More

7 Rentals

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1 / 16

Southold Home
3 Bedrooms / 2 Bathrooms / Sleeps 4

from

$167

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:4
Type:Home
Per night:$167
Per week:$1,167
Pets allowed:No
Internet:Yes

Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv,...

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1 / 5

Southold Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$400

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$400 - $500
Per week:$2,000 - $2,250
Pets allowed:No
Internet:Yes

This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The...

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GREAT RENTAL HOUSE

“ Excellent ”
September 16, 2014
The house is large and well kept. It was clean and had many amenities like wi-fi, many tv channels, air conditioning, and a security system. It is on a lake, and there were 2 canoes which we enjoyed using. It is in a great location on eastern Long Island. The owner was very helpful and communitcative.
Carol Melchner Reed, Coral Springs, FL

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Our own piece of Paradise, Paradise Shores beach just a short walk away
1 / 11

Southold Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$295

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$295 - $475
Per month:$8,850 - $14,250
Pets allowed:Yes
Internet:Yes

Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide ...

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2 bed cottage to the left, detached studio in the foreground
1 / 10

Southold Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$295

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$295 - $575
Per month:$8,850 - $17,250
Pets allowed:Yes
Internet:Yes

Newly renovated waterfront cottage with detached studio This property consists of two separate buildings, a two bedroom house and a detached studio cottage . From September through June only the studio (sleeps 2) is available for rent. In July and August both the 2 bedroom cottage...

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Great property

“ Excellent ”
September 4, 2014
We definitely enjoyed staying in this cottage and studio. It was very nicely decorated, clean and in a very quiet area. The beach is 1 min walk. All the nice villages are close by.
dorota huret, France

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Southold New York Vacation Rentals - Home
1 / 8

Southold Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 8

from

$499

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$499 - $599
Per month:$14,970 - $17,970
Pets allowed:Yes
Internet:Yes

Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and enlarged to double the footprint this winter with new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque inlet...

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Water view from deck
1 / 12

Southold Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

“ Excellent ”3 Reviews

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$250 - $365
Per month:$7,500 - $10,950
Pets allowed:No
Internet:Yes

Our immaculate waterview beach house is located in a beach and boating community in Southold, New York, only a mile from the historic village of Greenport. It's the perfect place to relax and take in the North Fork's pristine beaches, award- winning wineries, antique shops,...

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A Perfect Vacation

“ Excellent ”
July 7, 2010
This was one of the best vacations we ever had. The home was warm, inviting, and immaculate. We were greeted with a bountiful welcome basket of fruit, vegetables and bread. The house has everything you can think of and is very comfortable. The street is tree-lined and quiet and the little beach is a tranquil peace of heaven. Loved it! Loved it!
The Kenny Family, Hawthorne, New York

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1 / 8

Southold Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$200

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$200 - $285
Per week:$1,200 - $1,800
Pets allowed:Yes
Internet:No

This charming summer cottage is unique in the sense that it is located in the private community of Reydon Shores, and is just walking distance to a private beach and marina. The special feature is its wrap around enclosed porch with a view of the Peconic Bay. If you enjoy the...

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