Holiday Homes in Town of Southold Town

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Top Cities in Town of Southold Town

Featured Holiday Homes in Town of Southold Town

Another rental season is coming up.

10.0 out of 10, Exceptional, (21)
"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.

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (135)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Aqua Vista

10.0 out of 10, Exceptional, (18)
"This was our second stay at Aqua Vista. We love the property. The house is recently renovated and everything is brand new. It is nicely decorated and very comfortable. It is located close to the beach and center of the town with all of the restaurants. The property manager is a great host. We enjoyed our visit to the fullest."
Aqua Vista

Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay. The house is perfect and close to everything. The beach was delightful and ideal for children. "
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is AU$552
includes taxes & fees
1 Sept - 2 Sept
American Beech in Greenport - Petite King Room 7

Beach, Pool, Wine, Shopping!

10.0 out of 10, Exceptional, (67)
"The check-in process and communication couldn't have been easier. The property was clean, comfortable, and had everything we needed to enjoy ourselves. Conveniently located a walkable distance from Love Lane and a short drive from wineries (which is what brought us to the area)"
Beach, Pool, Wine, Shopping!

Historic Luxury Seaside Getaway

10.0 out of 10, Exceptional, (34)
"We loved o weekend getaway with the family. The house was beautiful. Everything was perfect. "
Historic Luxury Seaside Getaway

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

10.0 out of 10, Exceptional, (178)
"The house and property were perfect for our group of friends to visit the north fork for a weekend. Lots of beds and bathrooms, and beautiful spacious indoor living area and kitchen. Outdoor space was wonderful! Deck, hot tub, firepit, osprey nest just across the water, front porch, and beach a short walk away. Southold is a great little town with lovely restaurants and the perfect central location for visiting wineries. Owners were great to work with, very quick to respond to messages. Loved it...
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

Cozy North Fork Home Close to Beaches, Wineries, and Town, Perfect for Families

Cozy North Fork Home Close to Beaches, Wineries, and Town, Perfect for Families

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

10.0 out of 10, Exceptional, (6)
"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.

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"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!

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

9.4 out of 10, Exceptional, (9)
"What a lovely and peaceful location for a relaxing get away. This place checked all the boxes for us - right on the water (with kayaks and paddle boards to enjoy), fire pit in the sand right on the beach, heated pool (a bit finicky but we got the hang of the heating system), hot tub, nicely equipped kitchen, high quality linens and thoughtful touches throughout the home. Really nice stay!"
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

North Fork Paradise

10.0 out of 10, Exceptional, (1)
"Lovely home. Excellent hosts. "
North Fork Paradise

Cozy Seaside Cottage

10.0 out of 10, Exceptional, (37)
"Loved our stay at Whitecap. Great location, spotlessly clean. Very comfortable with everything you need for a wonderful stay."
Cozy Seaside Cottage

Water front beach house w/ private beach with 3 bedrooms/2 bathrooms/Large Deck

9.4 out of 10, Exceptional, (8)
"Overall great experience. Relaxing and quiet escape."
Water front beach house w/ private beach with 3 bedrooms/2 bathrooms/Large Deck

Spacious Beach House, Steps to Beach

10.0 out of 10, Exceptional, (18)
"Another wonderful stay at this beautiful home in Mattituck. The house has everything you need and the hosts are first rate. The perfect get away."
Spacious Beach House, Steps to Beach

Breakwater Estate… perfect for Large Group Getaways!

10.0 out of 10, Exceptional, (34)
"House was great and in a great location. We loved the pool, beach, and surrounding farms/towns!"
Breakwater Estate… perfect for Large Group Getaways!

Elevated North Fork Escape with Chic Interiors and Private Poolside Oasis -...

Elevated North Fork Escape with Chic Interiors and Private Poolside Oasis -...

North Fork Family and Friends Getaway. Great Location

10.0 out of 10, Exceptional, (14)
"We had a great stay! The house had everything we needed and was in a wonderful location to explore the North Fork. Barbara was incredibly gracious - very responsive and helpful. We hope to make a return visit!"
North Fork Family and Friends Getaway. Great Location
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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Top Town of Southold Town Hotel Reviews

Find out more about Town of Southold Town

Find out more about Town of Southold Town

Town of Southold Town Holiday Homes information

Number of reviews
Accommodation
249 Holiday Homes
Lowest Price
AU$552
Highest Price
AU$552