Located in the heart of wine country/BEACHES/shops.

3 bedrooms, free WiFi, bed sheets, wheelchair access

10.0 / 10.0

Outstanding(66 Ratings)

House in Southold, NY

8 guests · 3 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceOne of the higher cost properties in the area

Includes essentialsGarden, Pool, Kitchen or Kitchenette and more

About this house rental

Historical home full of charm. A home built in the 1700's this home maintains the historical feel with all the amenities of today. This well appointed home is perfect for a relaxing vacation. 3 bedrooms, 2 living rooms, finished sunroom which leads to an english patio and acre of fenced in property. Across the street from a creek, yards from boat ramp and a block away from a private beach. A nice walk into town and a short drive to the wineries.

Regarding Short Term Rental Laws: The Town of Southold recently passed legislation requiring a minimum stay of 14 nights in private homes. We can rent for shorter periods of time but we cannot create another separate reservation within the same 14 night period. Therefore in the case that we accept a shorter stay we will block out the unused nights and only charge for those being occupied.

Sleeps 8

Check-in time 4pm
Check-out 11am

Please contact Carrie if you would like to arrange for a different check-in or check-out time. Check in/out changes must be requested at least 3 weeks before check-in.

Amenities

Pool

Air conditioner

Kitchen or Kitchenette

Internet / Wifi

Parking

Laundry

Balcony or Patio

Dishwasher

Wheelchair accessible

Garden

Family friendly

Map of Southold, NY

Nearby attractions

Montauk Point State Park

46.1 mi

Mystic Aquarium

53.4 mi

Gillette Castle State Park

41.1 mi

Montauk Lighthouse Museum

48 mi

$$$$

Located in the heart of wine country/BEACHES/shops.

$$$$

10.0 / 10.0

Outstanding(66 Ratings)

House in Southold, NY

8 guests · 3 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceOne of the higher cost properties in the area

Includes essentialsGarden, Pool, Kitchen or Kitchenette and more

About this house rental

Amenities

Pool

Air conditioner

Kitchen or Kitchenette

Internet / Wifi

Parking

Laundry

Balcony or Patio

Dishwasher

Wheelchair accessible

Garden

Family friendly

Map of Southold, NY

Nearby attractions

Montauk Point State Park

46.1 mi

Mystic Aquarium

53.4 mi

Gillette Castle State Park

41.1 mi

Montauk Lighthouse Museum

48 mi

Ratings and reviews

10.0 / 10.0

Outstanding(66 Ratings)

10.0 / 10.0

Sep 2024

We absolutely loved this place! We were in town for a wedding and wished we had more time to enjoy the house. So cute and clean.

10.0 / 10.0

Sep 2024

Truly enjoyed the home and the old character of the structure ❤️

10.0 / 10.0

Aug 2024

Such a lovely house! Honestly the pictures don’t do it justice. There is so much history & charm throughout the property. Carrie was very communicative & reached out the second we arrived. There were 7 of us staying, and honestly we made it work with the single shower. It helped that there were two other bathrooms and a tub too. Would absolutely stay again!

10.0 / 10.0

Jul 2024

We stayed for a wedding at The Peconic Yacht Club and it was so close! House was big and the upstairs was great for my older girls.

8.0 / 10.0

Jul 2024

Great location. Home is a little quirky.

10.0 / 10.0

Sep 2023

Great Stay! Carrie was very easy to deal with

10.0 / 10.0

Sep 2023

We had an amazing long weekend at Carrie’s house! It’s super clean as many others have reviewed, in a perfect location for access to the town shops, and has a really cozy vibe that our family truly enjoyed. We would 100% stay here again!

10.0 / 10.0

Aug 2023

We had a great stay at the Cocktail Cottage. You could feel the history on the property and that was very unique. The house and the grounds are in great shape and we would gladly stay there again!!!

10.0 / 10.0

Aug 2023

My family and I used to live in Mattituck and we visit once a year and wanted to try VRBO to give us more space. This was the perfect house for us. We loved the history behind it, we felt the good energy and love in the house, we loved the sunroom and big yard. At night we would talk over wine in the sunroom or living room and in the mornings we would sip over coffee and bagels on the patio. My sisters and I would dance in the yard. The ground felt so good under our feet. The beds and temperature in the house was comfortable so we all had a good nights rest so we were fresh for the adventures in the day. We also loved how close it was to the beach and the grocery store. Will definitely look to see if this house is available the next time we visit!

10.0 / 10.0

Aug 2023

We had a wonderful stay in this beautiful home. It was perfect for our needs. In a great central location to everything on the island. We were there to spread my mother-in-law's ashes near her old home place, with a group of 8, (9mth old, 6 yrs old, 9 yr old, 20 yr old, 26 and 27 yr old, my husband and myself) This historic home is not only beautiful but also sooo comfortable. It is big enough that our group had plenty of room to spread out and do our own things or come together to watch tv or play games. The kitchen in this house is perfect. It has everything you could possibly need to cook an amazing meal. I am totally jealous of the amount of cabinet and counter space it has!! Everything is provided for you, down to aluminum foil and paper towels, even a good selection of spices! The beds are comfy and have quality linens! The AC is cold, and the sunroom with the available video game system was a big hit with our kids and grandkids! The check-in and out was so easy and the host was so accommodating and easily reached by text message if needed. If we are ever looking for a place to stay in the area again this place will definitely be our 1st choice! Thank you for a beautiful and welcoming home away from home for our weekend trip!

10.0 / 10.0

Jul 2023

Our stay was incredible and we were very impressed with the home and all of the amenities. We would gladly stay there again and would highly recommend it. Bravo!

10.0 / 10.0

Jul 2023

We're former Southold residents who were back in town visiting for my nephew's high school graduation. Carrie's house was in a great location and very comfortable for our group of five adults and a three-year-old. If you're traveling with little ones, you do need to keep an extra eye on them since there are a lot of antiques in the home and the stairs are very steep. Carrie was a great host and communication was prompt. We hope the house will be available for us again in two years when my niece graduates!

10.0 / 10.0

Jun 2023

Loved your home Carrie. Can’t wait to come back.

10.0 / 10.0

Jun 2023

Lovely spot for our family to relax and reconnect from across the country as we gathered for a wedding near by (Peconic Yacht Club). Well equipped house, quality linens and bedding, lovely antiques in every room made it comfortable and an interesting place to stay. Highly recommend for an adult group.

10.0 / 10.0

Nov 2022

Perfect

10.0 / 10.0

Oct 2022

The house was perfect for our gathering. The communication process was very easy and the property owners were very accommodating. Thank you.

10.0 / 10.0

Sep 2022

Amazing time had by all. Great kitchen totally equipped. The owner Carrie makes sure you have everything you possibly need for a great stay. We rented bicycles and rode into town, to the beaches, wineries etc. Great location close to all

10.0 / 10.0

Aug 2022

I enjoyed staying here. It is clean and comfortable and is very close to all the wineries. If I come back to the area I definitely stay at this location.

10.0 / 10.0

Aug 2022

My friends and I (5 in total) loved staying in this home for a long weekend to explore the North Fork area. This home is even better than pictured, it’s an older home which gives it great character, but also has modern touches such as the kitchen and beautiful shower in the master bath. There were so many sitting areas. My friends and I enjoyed meals at the kitchen table and sitting on the indoor porch and outdoor patio for breakfast. It’s in a very cute neighborhood and very close to many towns/attractions/ wineries/ shelter island ferry. It was a lovely stay, I would highly recommend and I hope to return here one day.

10.0 / 10.0

Jul 2022

Southold is one of the most magical places to visit. Quiet beaches, abundant wineries, great biking, good farmsteads and good fish markets We loved being able to walk to town, less than a mile away. Goose Neck Beach was fun for kids and adults. Greenport a short distance away.

10.0 / 10.0

Jul 2022

It was an excellent experience. The house is immaculate & well stocked. What a lovely home! The host is readily available to help in any way possible.

10.0 / 10.0

Jun 2022

House was beautiful, rustic, historical. We were very comfortable and had a wonderful time!

10.0 / 10.0

May 2022

Just as advertised. The house had plenty of a space for our group. The property manager was very easy to contact and answered all questions promptly. Definitely will use this property again.

10.0 / 10.0

May 2022

Girls weekend away and this little cottage was the best part of the whole trip! Located right in the heart of wine country, with an amazing back yard to enjoy cocktails, music and fun!!

5.0 / 10.0

Dec 2021

We enjoy our stay very much. There is lots room, and many options, to both spread-out and meet together. Carrie was an attentive and helpful host.

5.0 / 10.0

Oct 2021

Carrie was an incredible host. Myself and 3 girlfriends went for the weekend. Carries house was in the best location. We were able to take a beautiful walk around the neighborhood, take a short drive to Greenport for shopping and enjoy the wineries!!! We can’t wait for next time!!

5.0 / 10.0

Oct 2021

We had such an amazing trip! The house was even better than the pictures online & Carrie was extremely kind & helpful!! We will definitely be back!

5.0 / 10.0

Aug 2021

Carrie is an excellent host. The house is spacious with plenty of rooms for everyone to work and relax. Kitchen is big and bright with a nice breakfast nook adjacent. Baths and bedrooms all excellent. Patio is great for barbecuing and dining. The house is in a great location. Wonderful experience overall.

5.0 / 10.0

Aug 2021

Beautiful space. Close to beaches and wineries. Clean home and beautiful property. Owner a breeze to deal with. Thank you.

5.0 / 10.0

Aug 2021

Very close to beach and wineries and markets. Enjoyed our stay

5.0 / 10.0

Aug 2021

The kitchen was well-stocked with appliances, dishes, cutlery, and spices, though the dish ware might be fragile for families with young children. The patio area was quite spacious and inviting. Nice welcome basket, beach towels and beach chairs. Comfy master bedroom. Layout is a bit quirky as it is an antique home, but it was livable and interesting to explore. Nice central location for exploring the North Fork. Carrie was a great host!

5.0 / 10.0

Jul 2021

This property is perfect, the home is huge and comfortable, beds were very comfortable, the kitchen is quite large and has everything for cooking eating and drinking, Omally's in Southold has awesome food and if your craving Italian, Michaelangelo's was fantastic, we are Greenport lovers, you can be there 7 or 8 minutes by car or cab. You can contact Carrie the host if you have any questions she was lovely to deal with I could go on and on but just want to say we had a fantastic stay.

5.0 / 10.0

Jul 2021

We travelled for a family wedding and found Cocktail cottage to be beautiful , well-equipped and very comfortable. Carrie was very responsive to any questions that we had. Could not have been a nicer stay!

5.0 / 10.0

Jul 2021

We had a lovely time at this very special house full of historical details. Great outdoor space with large patio was great for hanging out and eating dinner, plus a glassed in porch with French doors with lots of games for the kids. The stairs up to the second floor were a little steep, so might not be best for toddlers (plus you might be nervous about them breaking all the cool decorative objects that are around). Owner was very responsive via text to any issues.

5.0 / 10.0

May 2021

My wife and I were looking to take our young children to the North Fork for a few days. The Cocktail Cottage was a perfect place to stay. It’s centrally located with short drives to wineries, Mattituck, Greenport, and Orient Beach State Park. Carrie was very responsive and a great host. We had a wonderful time.

5.0 / 10.0

May 2021

We had a fabulous weekend at Carrie's charming and cozy home. It was nicely appointed with everything we needed. We enjoyed riding and running in the neighborhood. It is close enough to walk to at least the nearest winery. And Sophie's restaurant is just down the block. Good food, friendly folks. We had so much fun and have great memories to treasure!

5.0 / 10.0

Sep 2020

Carrie and the house were amazing! Would definitely recommend !

5.0 / 10.0

Sep 2020

Our stay was perfect. It was so charming, so clean and the location down the road from Goose Neck Creek! We had our 2 daughters and our 4 grands all under 5. The house had plenty of space for all. There were games for the kids and a wonderful patio and fenced in private yard. The kitchen was a real gourmet kitchen so well stocked with good pots etc. Like staying at Martha Stewarts. Every detail was thought out and felt like staying at a b & b. Carrie was amazing. Anything you texted her she responded within seconds. We cannot wait to come back. So special a find. :)

5.0 / 10.0

Jul 2017

We had a very enjoyable stay here for a girls weekend getaway. The house is in great condition and we thoroughly enjoyed the kitchen and backyard space for group meals. We also rented bikes and biked to nearby wineries and beaches. Great stay overall and easy and helpful communication with Carrie. Definitely recommend!

5.0 / 10.0

Jul 2017

My wife and I stayed here for 3 days visiting family. A historic old tavern with all the amenities of modern life. Beaches and stores are right down the street. Carrie was a great communicator and made sure we where settled in. Would definitely stay here again!

FAQs

How much does this house cost compared to others in Southold?

The average price for a rental in Southold is $772 per night. This rental is $0 less expensive than the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Located in the heart of wine country/BEACHES/shops.. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

Yes, a swimming pool is available for use at Located in the heart of wine country/BEACHES/shops.. Enjoy the water!

Is Located in the heart of wine country/BEACHES/shops. pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Located in the heart of wine country/BEACHES/shops.?

We found 12 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and parking.

Explore similar vacation rentals in Southold

Explore all rentals in Southold

Beachfront

8.1 / 10.0

Excellent(241 Ratings)

Sound View Greenport

Hotel

in Greenport

3star

1 sofa bed, 1 queen bed

Pool · Pets allowed · Kitchen or Kitchenette

Experience the best of Southold with this Hotel available for $264. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

Located in the heart of wine country/BEACHES/shops.

House in Southold, NY

Reasons to book

About this house rental

Amenities

Map of Southold, NY

Nearby attractions

Located in the heart of wine country/BEACHES/shops.

House in Southold, NY

Reasons to book

About this house rental

Amenities

Map of Southold, NY

Nearby attractions

Ratings and reviews

FAQs

How much does this house cost compared to others in Southold?

Is parking included with this house?

Is there a pool at this house?

Is Located in the heart of wine country/BEACHES/shops. pet friendly?

What amenities are available at Located in the heart of wine country/BEACHES/shops.?

Explore similar vacation rentals in Southold

Southold travel inspiration

Related vacation destinations