Town of Southold Town Holiday Rentals

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Top Holiday Rentals Destinations in Town of Southold Town

Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (179)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is AU$494
includes taxes & fees
1 May - 2 May
Cliffside Resort Condominiums
Pool
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
On the beach
Entire, new, roomy, village beach house close to beach, park, and town center
10.0 out of 10, Exceptional, (8)
"We had a great time in Greenport. Nice low-key neighborhood. Easy walk or bike ride into town and very close to ferry. Freeport is sweet and had enough restaurants and shops to keep us entertained for a couple days. It’s close enough to the Shelter Island and more for further exploration. We made use of the bikes, which was great. The house has lots of space and is well cared for. The hosts were very responsive and available."
Entire, new, roomy, village beach house close to beach, park, and town center
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Fridge, microwave, oven, stovetop
Fabulous Waterfront Property in the Heart of Wine Country
10.0 out of 10, Exceptional, (153)
"Lovely home! Beautiful view! House has everything you need."
Fabulous Waterfront Property in the Heart of Wine Country
Outdoor pool
Enjoy the North Fork of Long Island at Our Lovely Home
Enjoy the North Fork of Long Island at Our Lovely Home
Property grounds
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
10.0 out of 10, Exceptional, (10)
"Perfect spot for a weekend on the North Fork"
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Beach nearby
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
9.2 out of 10, Wonderful, (5)
"Lovely location!"
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
Exterior
Charming Greenport Gem 1, 1 Mile to Ferry!
10.0 out of 10, Exceptional, (6)
"Most amazing house in a perfect location! The host could not be any more accommodating. We will definitely come back!"
Charming Greenport Gem 1, 1 Mile to Ferry!
Beach
MATTITUCK, North Fork's #1 Winery & Beach Town!
10.0 out of 10, Exceptional, (97)
"You cannot go wrong staying at Manny’s place. It is a short walk to the beach, which has great views and short drive to most vineyards and restaurants. The property itself is beautiful, and there is a private entrance to the rental, which is very roomy, immaculate, and you get a welcome bottle of local wine and hopefully you get Amal’s cookies and chocolate. As mentioned in other reviews, Manny is unintrusive, but very approachable, he is a great source of information as to the best restaurants...
MATTITUCK, North Fork's #1 Winery & Beach Town!
Property grounds
The SandPiper
9.4 out of 10, Exceptional, (3)
"This listing was exactly as described and was a great little apartment in Greenport with everything we needed. About a 10 minute walk to downtown area which was very convenient. It sits on a busy street so there is some noise from the road but it did not bother us too much and the host provided noise machines in the bedrooms which was very helpful. Overall I recommend this apartment and would definitely stay in the future!"
The SandPiper
Bar (on property)
Sea Breeze Paradise: Beachfront & Panoramic Views
9.4 out of 10, Exceptional, (16)
"We've found that fall is a great time to visit the North Fork and the property was the perfect place for relaxing. Even when the weather was bad, we had the indoor fireplace to add ambiance and then the outdoor firepit when the weather cleared up. The views are fantastic and so nice to sit outside and relax at night. Had a couple of quick questions come up but got responses very quickly and it didn't interrupt the trip. We had a great time."
Sea Breeze Paradise: Beachfront & Panoramic Views
Smart TV, fireplace, books, printers
Spectacular Beachfront Contemporary ~ Wine Country
10.0 out of 10, Exceptional, (151)
"Fun!"
Spectacular Beachfront Contemporary ~ Wine Country
Fridge, microwave, oven, stovetop
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
10.0 out of 10, Exceptional, (15)
"Comfortable, well appointed home. Beds were comfortable. Everything was super clean. We were very pleased with our stay and would definitely return."
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Pool
Respite Ranch: Private Pool, Hot Tub, Beach Access
10.0 out of 10, Exceptional, (2)
"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
Beach nearby, beach towels
Beach, Pool, Wine, Shopping!
9.8 out of 10, Exceptional, (49)
"This spot is where you want to be if you love the chill North Fork vibe and small town feelings from Mattituck to Orient Point. We will be back- actually we wish we were still there!! :)"
Beach, Pool, Wine, Shopping!
Sun-loungers, beach towels
Historic Luxury Seaside Getaway
10.0 out of 10, Exceptional, (30)
"Had friends and family at whitecap for a wine weekend. House was beautiful and clean. Close to so many vineyards and the walk to the beach was amazing. Can’t wait to stay again!"
Historic Luxury Seaside Getaway
Beach
Cozy Seaside Cottage
10.0 out of 10, Exceptional, (28)
"It was good."
Cozy Seaside Cottage
Fridge, microwave, oven, stovetop
Cozy Cottage on the North Fork Close to Vineyards & Beaches
9.8 out of 10, Exceptional, (33)
"Perfect place to stay for the weekend! We had a lovely time. The cottage was adorable in the host was very helpful."
Cozy Cottage on the North Fork Close to Vineyards & Beaches
Property grounds
Modern Farmhouse Steps to Beach and Love Lane
10.0 out of 10, Exceptional, (31)
"The property was the perfect stay for a weekend getaway!"
Modern Farmhouse Steps to Beach and Love Lane
Property grounds
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
10.0 out of 10, Exceptional, (161)
"As always, a great stay in Southold! Mike and family had a warm welcome for us. Plenty of space, great kitchen and lots of time out by the fire pit! Highly recommend! Thank you!"
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
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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.

Everything you need to know about Town of Southold Town holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Southold Town holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Southold Town holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Town of Southold Town holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Southold Town. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Southold Town holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Town of Southold Town holiday rentals we have chosen for you start as low as AU$428 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Town of Southold Town rentals

At Expedia, we put the best Town of Southold Town holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Southold Town rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Southold Town holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Southold Town. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Town of Southold Town Holiday Home Travel Info

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