Entire home

Charming Cottage

Photo gallery for Charming Cottage

A stone pathway leading through a lush garden with a hammock and a large tree in the background.
A small house with a green door and windows, surrounded by lush greenery and white flowering trees.
A bedroom with a bed, a nightstand, a lamp, a mirror, and a ceiling fan.
A bedroom with a bed, two bedside lamps, a window with blinds, and a view of greenery outside.
A bedroom with a bed, a ceiling fan, and windows with blinds.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Southold, NY
  • Place, The Old Field Vineyards
    ‪2 min drive‬
  • Place, The Hamptons Beaches
    ‪41 min drive‬
  • Place, Cooper's Beach
    ‪56 min drive‬
  • Airport, Westhampton, NY (FOK-Francis S. Gabreski)
    ‪37 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Bathtub · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area

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About the area

Southold

Located in Southold, this cottage is by the sea. Horton Point Park and Greenport Carousel are local landmarks, and some of the area's attractions include Custer Institute and Observatory and Railroad Museum of Long Island. East End Seaport Maritime Museum and 8 Hands Farm are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
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Map
Southold, NY

What's nearby

  • The Old Field Vineyards - 2 min drive - 1.8 km
  • Raphael Winery - 6 min drive - 6.0 km
  • The Hamptons Beaches - 41 min drive - 50.6 km
  • Shinnecock Hills Golf Course - 47 min drive - 56.6 km
  • Cooper's Beach - 56 min drive - 62.9 km

Getting around

  • Southold Station - 6 min walk
  • East Hampton, NY (HTO) - 72 min drive

Restaurants

  • ‪Dunkin' - ‬8 min walk
  • ‪Sophie's Rest - ‬3 min drive
  • ‪Pridwin Hotel - ‬33 min drive
  • ‪Panoramica - ‬5 min drive
  • ‪North Fork Roasting Co. - ‬9 min walk

Frequently asked questions

Is Charming Cottage pet-friendly?

Yes, this property allows dogs (limit 3 total).

How much is parking at Charming Cottage?

On-site parking is available at the property.

What time is check-in at Charming Cottage?

Check-in begins at 3:00 PM.

What time is check-out at Charming Cottage?

Checkout is at 11:00 AM.

Where is Charming Cottage located?

Situated by the sea, this cottage is within 2 miles (3 km) of The Old Field Vineyards, Custer Institute and Observatory and Sparkling Pointe. Croteaux Vineyards and Horton Point Park are also within 3 miles (5 km). Southold Station is 6 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 37 out of 39 reviews
Rating 8 - Good. 2 out of 39 reviews
Rating 6 - Okay. 0 out of 39 reviews
Rating 4 - Poor. 0 out of 39 reviews
Rating 2 - Terrible. 0 out of 39 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our 4th time staying at the cottage. The place is immaculate, the location is perfect and Erin the hostess is wonderful to deal with.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming cottage. Had everything we needed. Host was very easy to communicate with. I would rent again.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We are returning guests to this property because of how beautiful it is and how great of a host Erin is! We will continue to come back and spend our weekend getaways here.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a great stay! The owner made it so easy. Comfortable, clean, quiet, pet friendly, awesome location. Everything you want in a good VBRO listing. Will visit again soon!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Erin made everything very easy and the cottage was perfect for a weekend getaway.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful property and host!

Such a cute property and excellent location! We can’t wait to stay again.
Stayed 2 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time. Beautiful and clean home in an excellent location.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic getaway. We always stay here if we can.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything we hoped for and more! Relaxing, great location, wonderful host.
Stayed 5 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

Great location. Walking distance to town and secluded back yard. Look forward to staying there again.
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful cottage in an idyllic setting. This home far exceeded our expectations. Host was wonderful and thoughtful. Highly recommend this lovely home.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful host and property! The backyard is spacious, and the home is truly charming. The space definitely exceed expectations!
Stayed 2 nights in Jun 2025
Response from VrboOwner on 24 Jun 2025
Thank you Catherine. We’re glad you enjoyed your visit. Come back soon, always welcome :)
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Cottage on the North Fork

The house was beautiful, clean and comfortable. We enjoyed our stay very much. Erin is a great host who was easy to reach.
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Erin was a great host! The cottage was clean and she had everything prepared for us. There were even snack and beer with a cold glass ready in the fridge! I’d highly recommend staying here!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paws approved!

Such a lovely cottage — cozy, clean, and perfectly located for a relaxing getaway. The host, Erin, was responsive, and made everything super easy. We, especially our pups, had a great stay and that is definitely why we returned will come back!
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely cottage,

Wonderful experience. Cottage was perfect in every way.
Stayed 2 nights in Feb 2023
Response from VrboOwner on 13 Feb 2023
Thank you Bernadette. It was a pleasure hosting you. Thank you again for taking such good care of our home. Hoping you come back soon, always welcome.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage is exactly as described. Great location and it was fully stocked with what ever you need. We had a great time and will plan on return to this great cottage again. Felix
Stayed 4 nights in Sep 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exactly what we needed!

Everything was great! Easy to find, clean, and had everything we needed. The host communicated well and we had no issues with anything. Would stay again!
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay at Erin's Charming Cottage! It was beautifully decorated, the kitchen was well stocked and the beds were very comfortable. The screen porch was an absolute highlight and where we enjoyed all our meals. The yard was lush and secluded, yet only a short walk to town and to the small local marina. Erin was a proactive and informative host, and we'd love to return another time to enjoy her hospitality and lovely cottage.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Cottage

Stayed at this beautiful cottage for the second time. Perfect location for traveling around the North and South Fork. The Cottage is immaculately kept and the Host, Erin is extremely nice. Highly recommend it.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house and property was beautiful, clean, and well maintained! The check-in was easy and homeowner was very communicative. My dog loved the huge and safely enclosed yard! The neighborhood is cute and there are numerous walkable places to eat as well as a number of farm stands on the way east from NYC.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

North Fork getaway

Perfect little cabin for a few days of chill time with our pups. The cabin is cozy and well appointed and very close to town. The backyard was a treat to relax in and have the dogs run around. We would absolutely love to come and stay again. Thank you!
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family get together

Family reunion for a relative’s 90th birthday party in Southold. It’s the second time we enjoyed this cottage and I was not disappointed. Comfortable, nicely appointed, convenient and private. Perfect for us.
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet Get-Away

This cottage is tucked back from the marina so you can enjoy a calming water view by walking out the front door and taking a few steps down the dirt road. The cottage is very thoughtfully appointed and a comfortable retreat for some relaxing time away from hustle and bustle.
Stayed 2 nights in Apr 2023
Response from VrboOwner on 18 Apr 2023
Glad you enjoyed your stay Mary. It was a pleasure hosting you & your pup. Thank you for taking such great care of our home…it was spotless! Hoping you return, always welcome :)
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great cottage in the north fork!

Cottage is great - exactly as described and probably even better. Erin was a wonderful host and had a lot of nice touches in the space to make it a cozy weekend. The backyard is large and fully fenced in which our little dog loved. Location is a short drive to many great wineries. Highly recommend a stay with a few close friends
Stayed 3 nights in May 2024
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