Town of Southold Town Vacation Rentals

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Featured Vacation Homes in Town of Southold Town

North Fork seaside retreat for design lovers
Property grounds
North Fork seaside retreat for design lovers
10.0 out of 10, Exceptional, (2)
"Awesome property with everything you need for a great getaway. European chic touches throughout and a location that is just fantastic!! Spectacular Sunrises on the deck with breakfast overlooking Orient Harbor, Bug Light, and Shelter Island are mesmerizing. The view and the setting just never gets old-a real gem!! Nicole was terrific to deal with - we’ll be back!!"
North Fork seaside retreat for design lovers
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
4 bedrooms, desk, iron/ironing board, WiFi
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful family vacation in this beautiful home. The host was super thoughtful about every detail to ensure a wonderful stay. We really appreciated the special touches. The house has plenty of space and the backyard and pool are amazing. We would definitely rent this house again and we highly recommend!!"
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
Stunning Beachfront Home ~ Family Friendly, Close to Wineries!
Smart TV, fireplace, books, printers
Stunning Beachfront Home ~ Family Friendly, Close to Wineries!
10.0 out of 10, Exceptional, (164)
"This home is absolutely beautiful. Everything posted is 100% accurate. Our family has been there twice and plan on going back next year for a fall weekend getaway."
Stunning Beachfront Home ~ Family Friendly, Close to Wineries!
Cozy Seaside Cottage
Beach
Cozy Seaside Cottage
10.0 out of 10, Exceptional, (31)
"We had a great time at the cottage. The neighborhood is beautiful, quiet and very close to the beach, and short drive to berry picking, vineyards etc. The house itself suited our needs very well. Lots of attention to details, amenities, and we especially enjoyed the large garden. We would definitely love to come back one day! "
Cozy Seaside Cottage
Respite Ranch: Private Pool, Hot Tub, Beach Access
Bar (on property)
Respite Ranch: Private Pool, Hot Tub, Beach Access
9.8 out of 10, Exceptional, (6)
"Great stay and wonderful property. The first stay that didn’t have a book and list full of restrictions and checkout instructions. After a whirlwind weekend celebrating our daughter ‘s engagement, this was a welcomed surprise! Everyone enjoyed their stay, including our two labs. Great fenced in yard that gave them plenty of room to exercise. We will be back!"
Respite Ranch: Private Pool, Hot Tub, Beach Access
Aqua Vista
Sun loungers, beach towels
Aqua Vista
10.0 out of 10, Exceptional, (6)
"Great spot for all things North-Fork"
Aqua Vista
Northfork Townhouse- walk to all/ newly renovated
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated
9.0 out of 10, Wonderful, (2)
"We had a great stay at this house! Host was incredibly communicative and kind. House was exactly what was picture in the photos. Short (and beautiful) walk to all the restaurants and shops in town. Book this place now!"
Northfork Townhouse- walk to all/ newly renovated
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
Beach nearby, sun loungers, beach towels
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
10.0 out of 10, Exceptional, (16)
"Great stay at this beautiful home. Listing was accurate including the private beach for the community. Easy access to Greenport, Orient Point, and many vineyards. The house had everything you needed to feel at home, rooms were spacious and there was an overall warm energy about the place. If I decide to visit this area again, I would stay here again! Thank you for sharing your home!"
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
Beach house cape in North Fork's wine country
Property grounds
Beach house cape in North Fork's wine country
10.0 out of 10, Exceptional, (2)
"House was beautiful as was the giant pool Backyard was like a sanctuary with bird feeders and beautiful maintained landscaping. Home was well stocked and beautifully maintained. "
Beach house cape in North Fork's wine country
Nature's Paradise: Private Dock & Water Views
Marina
Nature's Paradise: Private Dock & Water Views
10.0 out of 10, Exceptional, (5)
"My 3 daughters with their husdands and and small children stayed here for a family wedding weekend. The place is peferct. Clean open spaces for the kids Fully equipped with toys books etc. Definitely ***** Five Star. "
Nature's Paradise: Private Dock & Water Views
Brand New Charming Beach House
Beach
Brand New Charming Beach House
9.8 out of 10, Exceptional, (15)
"We've stayed in four different VRBO properties around Mattituck over the past four years and this was our favorite. Everything was clean and well cared for. Common areas were perfect for our group of four woman, would surely accommodate more. Centrally located to many golf courses and wineries and very close to Strong's Marina where we enjoyed live bands a couple of nights."
Brand New Charming Beach House
Perfect North Fork Escape Just Steps Away From The Beach
Beach
Perfect North Fork Escape Just Steps Away From The Beach
10.0 out of 10, Exceptional, (12)
"We loved staying at the Cleary home. It’s perfect for a family. The house is very well maintained, clean, charming, and has everything you need for a wonderful stay. The kitchen is well appointed, stocked with all the equipment and modern fixtures you need. The living area is wide and comfortable, and the bedrooms were just right for my wife & I and our two young kids. The outside space is a highlight - a great deck for dining and lounging with beautiful lighting, plus expansive grassy space for...
Perfect North Fork Escape Just Steps Away From The Beach
Peaceful. Unique. Modern
Beach nearby, beach towels
Peaceful. Unique. Modern
10.0 out of 10, Exceptional, (2)
"We spent the last few weeks of summer in this beautiful home! We didn’t want to leave at the end of our stay. Beautiful, spacious and well decorated with a gorgeous backyard and pool. And a great location too! We took nightly walks to the beach to watch sunset and rode bikes through the neighborhood. Close to Greenport village and some of our favorite vineyards. Our kids loved the bunk beds in the kids room and the trampoline in the backyard. This house has everything you need though for a fun...
Peaceful. Unique. Modern
Enjoy Autumn with us.
Pool
Enjoy Autumn with us.
10.0 out of 10, Exceptional, (11)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Enjoy Autumn with us.
🌟 Walk to the village ❤ of Greenport
Dining
🌟 Walk to the village ❤ of Greenport
10.0 out of 10, Exceptional, (3)
"We stayed at this lovely home in Greenport. It was very close to shops and restaurants, but very peaceful and a great location for exploring the North Fork. The house and rooms were bright and comfortable, and the decor was very tasteful."
🌟 Walk to the village ❤ of Greenport
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Property grounds
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
10.0 out of 10, Exceptional, (14)
"The property was in a good area. The property had a good flow to it. We felt comfortable. My only complaint would be to had a space sponge available. The one on the sink was falling apart. "
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
Interior
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
10.0 out of 10, Exceptional, (32)
"12 of us were in town for a friends wedding nearby and really enjoyed our stay at this place! The property is huge with plenty of parking and plenty space both inside and outside. Vicky was very communicative and gave us a tour, instructions for our stay, and recommendations in the area upon arrival. We were able to check-in early and our check-out time was flexible too which was super helpful given our large group and a late night at the wedding. If we ever need somewhere to stay on the North...
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
Sea Breeze Paradise: Beachfront & Panoramic Views
Interior
Sea Breeze Paradise: Beachfront & Panoramic Views
9.6 out of 10, Exceptional, (18)
"This one week stay was mainly with my wife and our very well behaved 3 year old Aussie-Mountain Doddle. Over the weekend two of our children and one of their friends joined us. The house is solid, spacious and nicely appointed. The 180 degree view of the Long Island Sound directly in front of us was magnificent."
Sea Breeze Paradise: Beachfront & Panoramic Views
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
Smart TV, stereo
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
10.0 out of 10, Exceptional, (39)
"I could not be happier with our choice. This home was perfect from start to finish. The kitchen was well equipped, the amenities ( beach gear, bikes, cooler, chairs,etc) were absolutely key, the beds were so comfortable, the bathrooms were stunning. Such a great value for me and my 6 friends! Southhold and Greenport had so many amazing places and things to do. I wish we could stay for a a few weeks. It's so hard to choose the right place for your vacation- but don't hesitate. I will be...
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
Historic Luxury Seaside Getaway
Sun loungers, beach towels
Historic Luxury Seaside Getaway
10.0 out of 10, Exceptional, (31)
"The stay at Whitecap was spectacular. The hosts are amazing and very responsive, our family had a wonderful time on the property!"
Historic Luxury Seaside Getaway
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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