Holiday Rentals in Town of Southold Town

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Featured Holiday Rentals in Town of Southold Town

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, (153)
"Lovely home! Beautiful view! House has everything you need."
Fabulous Waterfront Property in the Heart of Wine Country
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, (10)
"Perfect spot for a weekend on the North Fork"
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Entire, new, roomy, village beach house close to beach, park, and town center
On the beach
Entire, new, roomy, village beach house close to beach, park, and town center
10.0 out of 10, Exceptional, (9)
"This was a great house! Everythingwas perfect, the house was very clean and David was incredibly accomodating to all our requests and provifed great recommendations for places to visit. We will definitely be back"
Entire, new, roomy, village beach house close to beach, park, and town center
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Charming Greenport Gem 1, 1 Mile to Ferry!
Exterior
Charming Greenport Gem 1, 1 Mile to Ferry!
10.0 out of 10, Exceptional, (8)
"The property was in a great location with being walking distance from the restaurants in town and quick drives to wineries. The property was well kept and had a home like feel. The apartment was perfect and spacious."
Charming Greenport Gem 1, 1 Mile to Ferry!
MATTITUCK, North Fork's #1 Winery & Beach Town!
Fridge, microwave, oven, stovetop
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!
Spectacular Beachfront Contemporary ~ Wine Country
Smart TV, fireplace, books, printers
Spectacular Beachfront Contemporary ~ Wine Country
10.0 out of 10, Exceptional, (151)
"Lovely home, right on the bay, super clean, very well , wonderful owner."
Spectacular Beachfront Contemporary ~ Wine Country
Respite Ranch: Private Pool, Hot Tub, Beach Access
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
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, (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
Cozy Seaside Cottage
Beach
Cozy Seaside Cottage
10.0 out of 10, Exceptional, (28)
"Such an amazing and flawless experience! The whole process of checking in and instructions, plus the homeowner gave us recommendations for places to eat and fav wineries! The cottage was so cute, so so clean, so spacious. It was the perfect cottage for our girls weekend!! The location was beautiful! We walked to the beach in the morning and it was gorg!! It has a private lawn & outdoor space, that we were able to hang out in. We really felt at home the entire weekend!! I would highly recommend &...
Cozy Seaside Cottage
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
Property grounds
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
10.0 out of 10, Exceptional, (162)
"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
Pace's Place Close to North Fork Vineyards
Fridge, microwave, oven, stovetop
Pace's Place Close to North Fork Vineyards
10.0 out of 10, Exceptional, (33)
"Another great stay in Cutchogue. Our 6th year visiting the north fork and we couldn’t be happier with our accommodations and host!"
Pace's Place Close to North Fork 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, (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
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
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,...
The SandPiper
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
Sea Breeze Paradise: Beachfront & Panoramic Views
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
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
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
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (180)
"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 €261
per night
7 May - 8 May
Cliffside Resort Condominiums
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Pool
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Enjoy the North Fork of Long Island at Our Lovely Home
Outdoor pool
Enjoy the North Fork of Long Island at Our Lovely Home
Enjoy the North Fork of Long Island at Our Lovely Home
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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.

Holiday Homes in Town of Southold Town

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Recent reviews in Town of Southold Town
Expedia verified reviews

Sound View Greenport

Sound View Greenport

5/5 Excellent
"Beautiful location. Staff was friendly and helpful. Dining was delicious. Rooms were renovated and spacious "
A verified traveller stayed at Sound View Greenport
Posted 1 day ago
Sound View Greenport