Town of Southold Town Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Vacation Rentals in in Town of Southold Town

Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (185)
"Had issue with check in. Nothing sent to phone as stated because of limited cell service in area. Had to go to office to get room and code. They have wrong room and had to go back for correct room. This was frustrating because it was after the check in time, which is later than most properties. The unit was fine, bare bones with decor etc. shower in one bathroom was leaking. I have stayed on property few times. This time was definitely less impressive."
The price is CA $446
CA $569 total
includes taxes & fees
Jul 18 - Jul 19
Cliffside Resort Condominiums
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
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
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Fridge, microwave, oven, stovetop
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
10.0 out of 10, Exceptional, (30)
"Spacious comfortable and inviting home. Well-stocked everything. Lovely outdoor spaces and gracious hosts."
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Fabulous Waterfront Property in the Heart of Wine Country
Fridge, microwave, oven, stovetop
Fabulous Waterfront Property in the Heart of Wine Country
10.0 out of 10, Exceptional, (155)
"We loved our stay. The house was clean and had everything we needed. It is located a few minutes from the sound. We wished we have driven there sometimes but the parking lot is only for residents with permits, so we walked. The property overlooks Goldsmith inlet. We saw a lot of wildlife including swans and a deer which walked right through the back yard. The owner left a bottle of wine which was very nice and allowed for early check in and late check out. We would love to come back."
Fabulous Waterfront Property in the Heart of Wine Country
Sea Breeze Paradise: Beachfront & Panoramic Views
Property grounds
Sea Breeze Paradise: Beachfront & Panoramic Views
9.6 out of 10, Exceptional, (17)
"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
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
Beach nearby
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
9.0 out of 10, Wonderful, (9)
"Great house with everything you need for a fun weekend. Enjoyed the kayaks, deck, view, birds and surrounding area. Host was very welcoming and accommodating."
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
Charming Greenport Gem 1, 1 Mile to Ferry!
Exterior
Charming Greenport Gem 1, 1 Mile to Ferry!
10.0 out of 10, Exceptional, (8)
"My family and I visited for 3 nights in late April, and this was the perfect place for us! Conveniently located in walking distance to downtown Greenport, with ample street parking, and the unit was modern, clean and spacious. The home itself is beautiful and with a lovely, well-cared-for garden. Definitely recommend!"
Charming Greenport Gem 1, 1 Mile to Ferry!
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, (12)
"We loved the rental updates and clean close to town, marina and wineries."
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
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, (154)
"This house is amazing! Beautifully designed and everything we could think of was provided. We had a lot of fun together enjoying the water, the kayaks, and the paddle boards. It is quite special as it sits on a large piece of land and feels quite private. The adults enjoyed visiting some of the local vineyards; everyone enjoyed the local produce. The Long Island Aquarium is nearby, the kids and grands loved it! The Great Peconic Bay is stunning - always changing. On our last night we had a...
Stunning Beachfront Home ~ Family Friendly, Close to Wineries!
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
A heated pool
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
9.8 out of 10, Exceptional, (7)
"We had an amazing time at this property for Memorial Day weekend. A short drive to the center of town and surrounding vineyards. The neighborhood is quant and you can walk to the water. The property is well maintained and the backyard space provides you with your own private outdoor area where you can lounge and relax by the pool and firepit. A great rental for anyone!"
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
Respite Ranch: Private Pool, Hot Tub, Beach Access
Bar (on property)
Respite Ranch: Private Pool, Hot Tub, Beach Access
9.4 out of 10, Exceptional, (3)
"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
The SandPiper
Property grounds
The SandPiper
9.6 out of 10, Exceptional, (5)
"We highly recommend this place. Just like being home, had everything."
The SandPiper
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, (31)
"This is our second year staying at Vicky's property for our Staff Retreat. The hosts are just lovely, and the home is very special! It is on a beautiful property, perfect for enjoying your morning coffee on the front porch. As we were in town for a retreat we didn't get to enjoy the home as much as we'd like, but we would definitely stay here again!"
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
Beautiful home within walking distance to beach
3 bedrooms, 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
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
TV, stereo
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
10.0 out of 10, Exceptional, (38)
"Location, hosts, house - everything was great! Can’t wait to go back!"
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, (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
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
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, (17)
"My family of four went out for a four-day weekend and we had a fantastic time in this house! It’s the perfect size, super clean and beautifully renovated. It has everything you might need. It even had a beach bag with a speaker and a blanket/towels ready to go! It’s a great house for a family. This was our second year staying there and we absolutely loved our experience! Bill is a great host and checks in regularly. It’s close to all of the wineries on the main road and the beach is only a few...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Cozy Seaside Cottage
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
Peconic Sound Beach Home: Backyard & Vineyards
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
Cozy Cottage on the North Fork Close to Vineyards & Beaches
Fridge, microwave, oven, stovetop
Cozy Cottage on the North Fork Close to Vineyards & Beaches
9.8 out of 10, Exceptional, (34)
"My finance and I had our engagement party at Borghese Vineyard which is 5 minutes from the Cozy Cottage. When I found this property, I knew it would be perfect! I didn’t get to checkin myself until after the party but my finance was able to checkin before to shower and change. This was a perfect location for the two of us to unwind together after hosting a party for almost 100 guest. It was the perfect chance for the two of us to spend some time together and enjoy our engagement. The cottage is...
Cozy Cottage on the North Fork Close to Vineyards & Beaches
Don't see what you're looking for?
See all available properties in Town of Southold Town
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 $446 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 vacation 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 vacation.

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 Vacation Rental Travel Info

Popular accommodation
Town of Southold Town private vacation homes
International airport
Islip, NY (ISP-MacArthur)

Recent reviews in Town of Southold Town
Expedia verified reviews

Greenporter Hotel

Greenporter Hotel

5/5 Excellent
"Loved it"
A verified traveller stayed at Greenporter Hotel
Posted 3 days ago
Greenporter Hotel