Town of Southold Town Vacation Rentals

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Top Vacation Rentals in in Town of Southold Town

Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"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 CA $255
CA $350 total
includes taxes & fees
May 28 - May 29
Cliffside Resort Condominiums
Outdoor pool, a heated pool
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Fridge, microwave, oven, stovetop
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
10.0 out of 10, Exceptional, (29)
"This was the perfect Christmas House for our family while celebrating a 100th Family Birthday nearby. This is a beautifully appointed and true to period Victorian. The home is immaculate and incredibly well tended. The hosts were lovely and very responsive. This was a special stay and made more so by the wonderful surroundings and ease to town. We would stay here again."
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
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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
Property grounds
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
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
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!
Property grounds
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
10.0 out of 10, Exceptional, (3)
"Very nice property that is incredibly well maintained. We had a nightmare experience on Cape Cod two summers ago and this was just the opposite. Laura was super responsive and the home was everything you see in the photos with absolutely everything we needed for our stay."
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Bar (on property)
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
On the beach
Peconic Sound Beach Home: Backyard & Vineyards
9.8 out of 10, Exceptional, (6)
"Tucked away near the sound….a piece of paradise ! Truly a beautiful place to unwind and enjoy all the North Fork has to offer . Centrally located on the North Fork, but easy access to a spectacular beach . You will leave refreshed & trying to figure out how soon you can return ."
Peconic Sound Beach Home: Backyard & Vineyards
Fridge, microwave, oven, stovetop
MATTITUCK ! The North Forks #1 Winery & Beach Town !
10.0 out of 10, Exceptional, (98)
"Manny is a great guide for your visit. A very quiet and private place with a beautiful patio garden."
MATTITUCK ! The North Forks #1 Winery & Beach Town !
Smart TV, fireplace, books, printers
Spectacular Beachfront Contemporary ~ Wine Country
10.0 out of 10, Exceptional, (153)
"We had a fantastic weekend at this stunning home! It easily and comfortably slept our entire group and the views are stunning. It's a safe, quiet, and peaceful location for any group, and for those who want to go out, it's located just a few minutes from the famous wineries of the North Fork. Meredith was an outstanding host from the moment we booked this stay and communicated well through everything. We hope to come back to this gorgeous home in the future!"
Spectacular Beachfront Contemporary ~ Wine Country
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
Interior
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
10.0 out of 10, Exceptional, (29)
"A group of 8 women had a wonderful weekend visiting vineyards and this was the perfect location! The house was extremely clean and well stocked with everything we needed. Great communication with host, thank you!"
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
WiFi
Beautiful home within walking distance to beach
10.0 out of 10, Exceptional, (3)
"Everything was just like it was stated. Beside the bad weather, we couldn't have gotten something my perfect for the 7 of us. Plenty of room for us to enjoy our time. Will return!"
Beautiful home within walking distance to beach
Beach nearby
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
9.0 out of 10, Wonderful, (6)
"Lovely home set right off the water with a sprawling yard. Unfortunately the weather was not on our side but the town had so many wonderful shops and amazing places to eat that we didn’t miss a beat. The house was clean and comfortable set in a beautiful neighborhood ."
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
A heated pool
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
9.6 out of 10, Exceptional, (5)
"Beautiful, well appointed new construction in desirable Greenport area. Minutes to local vineyards and the shoreline. Comfortable for 3 couples. Kitchen was perfect for simple meals. Off season, so we didn’t get to use the pool but it looked amazing!"
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
TV, stereo
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
10.0 out of 10, Exceptional, (37)
"We had the best time visiting Sam & Matt’s place in Southold. The house is the perfect size for us- 3 adults and 3 kids plus 2 dogs. And it was an ideal location to explore all the north fork has to offer. We can’t wait to return!"
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
Beach nearby, sun loungers, beach towels
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
10.0 out of 10, Exceptional, (16)
"A surprisingly lovely 2 Br cottage, recently renovated and in excellent condition. Quiet neighborhood with a 10 minute walk to a local Peconic Bay beach. Great communication with owner/manager. Very convenient to enjoy the entire North Fork."
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Beach
Cozy Seaside Cottage
10.0 out of 10, Exceptional, (29)
"Cozy Seaside Cottage was a slice of heaven in the bayside village of New Suffolk! Tracy warmly welcomed our group of five women two hours ahead of checkin time, and toured us around answering any and all questions...as we were all unable to access the smart phone lock system, she promptly supplied us with manual keys, which suited us just fine! The historic cottage is beautifully decorated, maintained, and immaculately clean. Walking to beach frontage was 5 minutes at most...sunrises were...
Cozy Seaside Cottage
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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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Southold Town vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Town of Southold Town vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Southold Town vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Town of Southold Town vacation rentals we have selected for you start as low as CA $255 per night. Entering your travel dates in the search wizard you might find even better deals!

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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 vacation.

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Town of Southold Town Vacation Rental Travel Info

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