Holiday Rentals in Town of Southold Town

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Featured Holiday Rentals in Town of Southold Town

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (223)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is €255
includes taxes & fees
6 Jul - 7 Jul
Cliffside Resort Condominiums

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

The SandPiper

9.8 out of 10, Exceptional, (22)
"My friends and I stayed here for a night after a wedding. It was the perfect place to stay after a long day. Host was kind and helpful with anything I needed! "
The SandPiper

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (25)
"we had such a fun weekend out in southold! Cottage was perfect for us for a cold rainy weekend. Everything was so close to the house. Will definitely be back in the summer!"
Lovely Cottage in the Heart of Long Island Wine country

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views

MATTITUCK, #1 Winery and Beach Town !

10.0 out of 10, Exceptional, (104)
"Excellent location for exploring the North Fork. Short drives to all the best places and access to 2 private beaches. Manny and Amal are very friendly, hospitable and helpful."
MATTITUCK, #1 Winery and Beach Town !

NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!

2.0 star property
10.0 out of 10, Exceptional, (3)
"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!

Newly built ranch, beautifully landscaped with pool, large yard, patio,...

10.0 out of 10, Exceptional, (21)
"This property was gorgeous! It’s conveniently located right in the heart of Greenport and the nearby private beach was stunning! Highly recommend this location, can only imagine how perfect it’d be for the summer time!"
Newly built ranch, beautifully landscaped with pool, large yard, patio,...

Harbor Heights

9.8 out of 10, Exceptional, (9)
"perfect for visit to town and liked everything about our stay. "
Harbor Heights

Bright Apartment - 1/2 Mi to Greenport Harbor!

10.0 out of 10, Exceptional, (78)
"Great stay in Greenport. The hosts, accommodations are location are wonderful. Look forward to another visit."
Bright Apartment - 1/2 Mi to Greenport Harbor!

Gorgeous Greenport Beach House right on the Sound! Breathtaking views

9.8 out of 10, Exceptional, (6)
"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"
The price is €1,776
includes taxes & fees
27 Jul - 28 Jul
Gorgeous Greenport Beach House right on the Sound! Breathtaking views

Old meets new in this fully renovated 19th century farm house.

10.0 out of 10, Exceptional, (1)
"The house was spotlessly clean and well-maintained, making me feel comfortable right from the start. The location was perfect—local attractions and great restaurants, which made exploring the town very convenient. Walter was incredibly responsive and accommodating, always quick to reply to any questions or requests. Overall, I highly recommend this home for a friendly and hassle-free stay!"
Old meets new in this fully renovated 19th century farm house.

Contemporary Colonial home with pristine Peconic bay views, steps to...

10.0 out of 10, Exceptional, (7)
"Everything was spot on, hope to be back!"
Contemporary Colonial home with pristine Peconic bay views, steps to...

Another rental season is coming up.

10.0 out of 10, Exceptional, (14)
"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. "
Another rental season is coming up.

Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!

10.0 out of 10, Exceptional, (24)
"We loved our stay at this beautiful house. It was very clean and spacious for our 6 guests. We had a wonderful time and would recommend staying here if you are considering staying in Greenport! It’s close to the town, wineries, restaurants."
Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

9.4 out of 10, Exceptional, (6)
"You have a fantastic property. Very well maintained and all that was advertised. Loved the location and the people in the village. We look forward to coming back. Thank you"
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

10.0 out of 10, Exceptional, (176)
"Place was wonderful. Perfect for a family vacation."
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

Beautifully farmhouse

10.0 out of 10, Exceptional, (1)
"good experience"
The price is €1,027
includes taxes & fees
30 Jun - 1 Jul
Beautifully farmhouse

American Beech in Greenport - Petite King Room 7

8.8 out of 10, Excellent, (3)
"We thoroughly enjoyed our stay!"
The price is €313
includes taxes & fees
30 Jun - 1 Jul
American Beech in Greenport - Petite King Room 7
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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