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Charming Cottage

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Plenty of backyard seating. Your pups will have so much fun in the backyard!
Cottage is steps from a sliver of the beautiful Peconic Bay.
Front yard
Hammock, grill & large picnic table in the backyard.
Property grounds

Reviews

10 out of 10, Loved by Guests
Top 10% based on
2 bedrooms1 bathroomSleeps 41400 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Southold, NY
  • Place, The Old Field Vineyards
    ‪1 min drive‬
  • Place, Custer Institute and Observatory
    ‪2 min drive‬
  • Place, The Hamptons Beaches
    ‪33 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)

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

About this property

Charming Cottage

Charming cozy cottage located in the heart of the Northfork, East End of Long Island. Come explore the beautiful vineyards, farms & beaches, all within minutes from the home. Cottage is steps from the Town of Southold which offers excellent restaurants, cafes & adorable boutiques. Property sits on an acre & a half overlooking a sliver of the Peconic Bay. Located off a dirt road for the ultimate in privacy. Backyard is completely fenced in for the safety of your pup. All pups welcome! This home is impeccably maintained with high end furnishings, fully stocked chefs kitchen & luxurious linens. Bedrooms have blackout shutters for sleeping in late. Backyard has a Weber grill, hammock & outdoor furniture. And the evening star gazing is incredible. The enclosed front porch overlooks a sliver of the Bay, offering super comfy furniture for those lazy days, sipping coffee, reading your book. Cottage has a funky, cozy vibe, super relaxing. Start making your memories at this gem of a property! Welcome :)
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 3 total)
As per insurance policy, no PitBulls or Pitmix
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Return the keys
Key in the turtle please 🙏
Failure to complete these may result in a negative review from the host.
No parties. No cigarettes. Must not flush anything but toilet paper. Tampering with cameras will not be tolerated, you will be asked to leave.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

We should mention

This property does not have elevators

About the neighborhood

Southold

Located in Southold, this cottage is by the sea. Greenport Carousel and Camera Obscura are local landmarks, and some of the area's attractions include Railroad Museum of Long Island and East End Seaport Maritime Museum. 8 Hands Farm and Norman E. Klipp Marine Park are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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Map
Southold, NY

What's nearby

  • The Old Field Vineyards - 1 min drive - 1.8 km
  • Custer Institute and Observatory - 2 min drive - 2.5 km
  • Splish Splash Water Park - 29 min drive - 38.1 km
  • The Hamptons Beaches - 33 min drive - 53.2 km
  • Cooper's Beach - 44 min drive - 63.7 km

Getting around

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

Restaurants

  • ‪Dunkin' - ‬8 min walk
  • ‪Michelangelo's - ‬8 min walk
  • ‪North Fork Roasting Co. - ‬9 min walk
  • ‪Sunset Beach Restaurant - ‬31 min drive
  • ‪Southold General - ‬4 min walk

Frequently asked questions

Is Charming Cottage pet-friendly?

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

How much does it cost to stay at Charming Cottage?

As of Mar 29, 2026, prices found for a 1-night stay for 2 adults at Charming Cottage on Mar 29, 2026 start from $415, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite 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?

Check-out is at 11:00 AM.

Where is Charming Cottage located?

Situated by the sea, this cottage is within 2 mi (3 km) of The Old Field Vineyards, Sparkling Pointe, and Mattebella Vineyards. Croteaux Vineyards and Corey Creek Winery are also within 3 mi (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 labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 32 out of 34 reviews
Rating 8 - Good. 2 out of 34 reviews
Rating 6 - Okay. 0 out of 34 reviews
Rating 4 - Poor. 0 out of 34 reviews
Rating 2 - Terrible. 0 out of 34 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jason K.

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

10/10 Excellent

Jim M.

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

10/10 Excellent

Verified traveler

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

10/10 Excellent

Joline M.

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

10/10 Excellent

Natalie T.

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

10/10 Excellent

Margaret B.

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

10/10 Excellent

Catherine P.

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
Verified

10/10 Excellent

Julia M.

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

10/10 Excellent

sean r.

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

10/10 Excellent

Felix A.

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

10/10 Excellent

Laura Lee B.

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

10/10 Excellent

Melissa I.

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

10/10 Excellent

Dena O.

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

10/10 Excellent

Maria M.

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

10/10 Excellent

Jim M.

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

10/10 Excellent

Bernadette L.

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

Lovely cottage,

Wonderful experience. Cottage was perfect in every way.
Stayed 2 nights in Feb 2023
Verified

10/10 Excellent

Nancy B.

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

8/10 Good

Laura L.

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

10/10 Excellent

Ann C.

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

10/10 Excellent

James R.

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
Verified

10/10 Excellent

Mary K.

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
Verified

8/10 Good

Geoffrey A.

Liked: Cleanliness, check-in, communication, location

Calming brief stay

We loved this cottage. The owners have done a great job at making your stay very comfortable. When we arrived it was hot and humid but the AC was on and made a huge difference. Kitchen was well stocked for cooking with all equipment available. Only disappointment was we thought it was on the water and it’s not.
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Nina C.

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

Great hideaway in the heart of Southold

I loved this cottage! So clean and comfortable. Everything was provided to make it seamless, nice towels, soft sheets, even the air was on when we arrived. The yard was ideal for my dog to run around in, the fencing is great! I just felt so immediately at home and was happy with just about everything. Will definitely come back if I’m on the North Fork again.
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Dana M.

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

North Fork Oasis

We love this house and have rented with Erin on multiple occasions. We love the house, fenced yard for our pup, screened porch and the location. It’s just a special place. So much so, ideally we’d like to keep it as secret as possible… ha! So charming, inside and out. We are already looking forward to our next visit.
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Amanda P.

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

Peaceful stay in Southold

We enjoyed two nights at Erin’s cottage in February 2024. The house was beautiful and unique and Erin had everything provided as promised and more. She also has a huge fenced in yard for dogs to run around in and that was the cherry on top! We could walk into town and there were wineries all around the area. Beautiful spot she has there, I would definitely go back!
Stayed 2 nights in Feb 2024

About the host

Hosted by Erin Leigh Streeter

Host profile image
Welcome to my cozy cottage. I am a plant based chef, animal lover of all kinds, jazz enthusiast, art & design junkie, love sharing my home with others!

Why they chose this property

Property sits in the heart of The NorthFork on the East End of Long Island, surrounded by 48 vineyards, countless farms, gorgeous beaches & amazing culinary delights. Walk to the charming Town of Southold, bike to the beaches, vineyards & farms. Cottage is super cozy, all high end amenities. Bring your pups! The huge backyard is completely fenced in. Dogs love it here :).

What makes this property unique

Within walking, biking distance to all that the NorthFork has to offer. And we are super doggie friendly!!

Languages:

English, Spanish

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