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Vacation Rentals in Southold, NY

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From
$250
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1 / 7
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$175
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1 / 21
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$295
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1 / 17
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3 Bedrooms, 1 Bathroom, Sleeps 6
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$175
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1 / 21
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • DVD Player
  • Parking
  • Washer
  • Grill
  • Dryer
  • Microwave
  • TV
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North... View all property information
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5 of 5 stars Reviewed June 3, 2014
I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway...
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$300
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1 / 15
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
3 bedrooms, 2 full bathrooms, sleeps 6 Pristine, year round, vacation getaway, within short walk to two white, sandy, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home.... View all property information
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$250
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1 / 18
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • TV
  • Microwave
  • Ceiling Fans
  • Safe
  • Dryer
  • Refrigerator
  • Stove
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Representing the owner's suite is the Unit One apartment in the Historic White Blossom House. Newly renovated, floors, kitchen and bath completely updated. Kitchen updated with period country deep sink and fixtures. You will be very comfortable in this large apartment with living room, family... View all property information
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$150
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1 / 19
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Internet Access
  • Satellite TV
  • TV
  • Washer
  • Refrigerator
  • Stove
  • Patio
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Step back in time as you enter a Historic Home in the heart of Southold....the charm of the historic home is clear as you enter the front door of your unit into the inviting hallway and stairs to the entire upstairs of the home. Just part of the charm is the refinished original 1830 floors, lower... View all property information
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From
$250
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1 / 13
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Waterfront
  • VCR
  • Satellite TV
  • Ceiling Fans
  • DVD Player
  • Refrigerator
  • Water Views
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
About this property
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
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1 of 5 stars Reviewed September 2, 2012
The photos in the add looked good, particularly the garden and the proximity of the lake. We rented the place for four days. When we arrived, the first thing that struck us was...
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From
$225
Per Night
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1 / 12
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Parking
  • Waterfront
  • Water Views
  • Microwave
  • Patio
  • Stove
  • Deck
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
About this property
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the... View all property information
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From
$2,400
Per Week
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1 / 12
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2 Bedrooms, Sleeps 6
Details Reviews (2) Make Inquiry
Amenities & Details
  • Fireplace
  • Stereo System
  • DVD Player
  • Grill
  • Dishwasher
  • Microwave
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
**New for 2013 Summer: Central Air, Paver Stone Patio Charming, bright, airy, two-bedroom home sits on cozy lot at the heart of the beautiful North Fork, just a minute walk to Southold's most sought after private community beach (Founders Beach). Our beautiful beach features a playground,... View all property information
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From
$300
Per Night
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1 / 40
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2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Grill
  • Dryer
  • TV
  • Refrigerator
  • Stove
  • Parking
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come experience a Northfork summer, golfing, biking, beaching, Estate sale hunting, in the Heart of Wine Country, Long Island. Centrally Located in the Town of Southold, South of the main road, 3 houses from the water in the elite Founders Landing section of North Fork, The cottage is minutes'... View all property information
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From
$250
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1 / 11
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Stove
  • Parking
  • Air Conditioning
  • DVD Player
  • TV
  • Satellite TV
  • VCR
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
John Andrew's Cottage is a 'turnkey' experience accommodating two adults and children including: -a cozy bedroom with its full size bed, which beckons you after a sun-filled day at the private beach (within walking distance) which overlooks Shelter Island -a complete kitchen and full bath -a... View all property information
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4 of 5 stars Reviewed August 22, 2014
my daughter (5 1/2 year old) and i had a great visit here. the cottage was cute and comfortable. having the backyard was great too. the hosts were very friendly and...
5 of 5 stars Reviewed August 26, 2013
We stayed at John Andrew’s cottage for my best friend’s bachelorette getaway and loved it. Karen was extremely helpful, had great recommendations all around (The Blue Canoe!) and...
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From
$500
Per Night
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1 / 20
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Microwave
  • Dishwasher
  • Garage
  • Dryer
  • Washer
  • Stove
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your... View all property information
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4 of 5 stars Reviewed June 16, 2014
We found the farmhouse to be charming and spacious for our seven family members. The location was beautiful with the vineyards and private beach, and it was also very handy for...
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From
$172
Per Night
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1 / 19
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Inquiry
Amenities & Details
  • Microwave
  • Dryer
  • Grill
  • DVD Player
  • Stereo System
  • Dishwasher
  • Refrigerator
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy, and... View all property information
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5 of 5 stars Reviewed August 18, 2013
This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold. We used for our...
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From
$295
Per Night
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1 / 10
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Ceiling Fans
  • Patio
  • Stove
  • Washer
  • Dryer
  • Dishwasher
  • Parking
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 and the studio... View all property information
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From
$250
Per Night
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1 / 12
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Stove
  • Washer
  • Grill
  • VCR
  • Dryer
  • Fireplace
  • Microwave
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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, art galleries, and... View all property information
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From
$200
Per Night
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1 / 8
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Microwave
  • DVD Player
  • Parking
  • Patio
  • Stove
  • Dishwasher
  • Grill
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 peaceful country... View all property information
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From
$321
Per Night
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1 / 5
4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Ceiling Fans
  • Grill
  • Dishwasher
  • Dryer
  • Stereo System
  • Microwave
  • Refrigerator
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 home has a central... View all property information
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From
$499
Per Night
View Details
1 / 8
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Stove
  • Washer
  • Grill
  • Fireplace
  • Refrigerator
  • Dryer
  • Ceiling Fans
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 in Southold, with... View all property information
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From
$167
Per Night
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1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Fireplace
  • Washer
  • Ceiling Fans
  • Grill
  • Parking
  • Stove
  • Dryer
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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, air conditioning and... View all property information
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From
$295
Per Night
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1 / 11
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Stove
  • Ceiling Fans
  • Dryer
  • Grill
  • Patio
  • Refrigerator
  • Parking
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 2 comfortable... View all property information
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