Search Town of Southold Town Cottages

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
In one month
In two months
In three months

Top Cities in Town of Southold Town

Cottages in Town of Southold Town

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (182)
"Beautiful view, clean house, great location "
Fabulous Waterfront Property in the Heart of Wine Country

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

9.8 out of 10, Exceptional, (99)
"My husband and I brought our puppy. He had a great time running around the yard and beach. We enjoyed our stay and hope to return. The property is beautiful and we were very happy to find a pet friendly place on the water and close to town."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Cottage on Beach front Estate with Dockage .Walk to Village

10.0 out of 10, Exceptional, (71)
"Myself my BF and my dog had a wonderful time."
Cottage on Beach front Estate with Dockage .Walk to Village

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (29)
"Our family stayed at this quaint cottage in the North Fork. The cottage has a nice kitchen, gas fireplace, and well appointed bedrooms. I would love to visit in summer, it must be wonderful!"
Lovely Cottage in the Heart of Long Island Wine country

Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!

10.0 out of 10, Exceptional, (13)
"What a great little get away weekend in a beautiful cottage in the middle of wine country. Great host a lovely accommodations"
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (27)
"The property was clean, exactly as advertised and extremely cozy and convenient. The host was super helpful and quick to respond!"
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

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

10.0 out of 10, Exceptional, (120)
"Lovely cottage on the Peconic Bay. We enjoyed our stay; found more than everything we needed. "
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Orient Village — Historic Bayfront Cottage — 2025 Season

10.0 out of 10, Exceptional, (23)
"Beautiful place with great views and a private beach! Great food and nature nearby, and very accommodating host!"
Orient Village — Historic Bayfront Cottage — 2025 Season

Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!

Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
$520 nightly
The price is $594
Nov 3 - Nov 4
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Walk to Breakwater Beach in Heart of Wine Country

9.8 out of 10, Exceptional, (13)
"Light filled, beautifully appointed home that was more than we expected. Gorgeous multiple outdoor areas. Seamless entry and exit. Would happily visit again. "
Walk to Breakwater Beach in Heart of Wine Country

Walk to Love Lane! Immaculately renovated private cottage.

10.0 out of 10, Exceptional, (18)
"My wife and I stayed for the weekend for our Anniversary and this was the perfect location. Quaint and quite hideout with tons to do nearby."
Walk to Love Lane! Immaculately renovated private cottage.

Charming 3-bedroom cottage in fabulous Greenport

10.0 out of 10, Exceptional, (1)
Charming 3-bedroom cottage in fabulous Greenport

Picture Perfect Greenport Cottage

Picture Perfect Greenport Cottage

Modern Cottage with New Heated Pool

10.0 out of 10, Exceptional, (22)
"Lovely property. Just perfect for a getaway. Convenient to Mattituck dining and shopping as well as to other towns on North Fork. Property owners were very helpful with any questions. Would love to stay and again and highly recommend it!"
Modern Cottage with New Heated Pool

Craftsman Cottage in Greenport Village

10.0 out of 10, Exceptional, (1)
"Me, my brother and sister in law, their son and his 1 year old daughter. The house suited us well. The house was well appointed and clean. Old craftsman house with nice modern kitchen and bathrooms. Bedrooms were a little tight with Queen beds but not a big deal. NIce big dining table for meals. Private back yard with picnic table. Quiet neighborhood with short walk to downtown."
Craftsman Cottage in Greenport Village

Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries

7.0 out of 10, Good, (9)
"My husband and I rented this cottage for most of the summer and couldn't be happier with it. We lovingly refer to this place as The Pond Shack. The house is small and rustic so if you want a luxurious rental, this isn't for you. But if you want a low key retreat at an unbeatable price in an absolutely gorgeous location with beautiful views of the Great Pond (it's really more of a lake) and a 5 minute walk to the beach, then look no further. This place is perfect for 2 couples or a couple...
Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries

Near Wineries: Historic North Fork Farmhouse!

3.0 star property
Near Wineries: Historic North Fork Farmhouse!

Southold Cottage w/ Patio & Grill - Walk to Beach!

3.0 star property
Southold Cottage w/ Patio & Grill - Walk to Beach!
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.
Save an average of 15% on thousands of hotels when you're signed in

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 Cottages information

Number of reviews
542
Accommodation
24 Cottages
Lowest Price
$594
Highest Price
$594

Explore a world of travel with Expedia

Explore a world of travel with Expedia