Entire home

Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach

Photo gallery for Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach

Pool
Exterior
Property grounds
Pool
Pool
3 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Private pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Southold, NY
  • Place, The Old Field Vineyards
    ‪16 min walk‬
  • Place, The Hamptons Beaches
    ‪42 min drive‬
  • Place, Cooper's Beach
    ‪56 min drive‬
  • Airport, East Hampton, NY (HTO)
    ‪75 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

1 bathroom, 1 half bathroom

Bathroom 1

Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 2

Towels provided · Toilet · Hair dryer

Spaces

Deck or patio
Kitchen
Separate dining area
Garden

About this property

Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach


Welcome to your perfect North Fork getaway! This bright and inviting 3-bedroom, 1.5-bath home is ideally located in the heart of Southold — walking distance to Founder’s Beach, local restaurants, charming shops, and yoga studios.

Each of the three bedrooms features a comfortable queen-sized bed with fresh linens provided, making it an easy and relaxing stay for families, couples, or friends traveling together.

Step outside and enjoy your own private backyard oasis complete with a large in-ground chlorine pool and diving board — perfect for summer afternoons and evening swims. The spacious grassy yard offers plenty of room for lawn games, relaxing in the sun, or dining outdoors.

Inside, you’ll find:
• A bright Florida room — ideal for morning coffee or evening cocktails
• Fully equipped kitchen
• 1.5 bathrooms
• Attached two-car garage
• Comfortable living spaces for gathering and unwinding

The location truly can’t be beat. You’re just minutes from:
• North Fork wineries & breweries
• Local farm stands & fish markets
• Pumpkin fields in the fall
• Christmas tree farms in the winter
• 10 minutes to the Village of Greenport

Whether you’re planning a beach weekend, wine tasting trip, or a relaxing poolside retreat, this Southold home offers the perfect blend of comfort, charm, and convenience.

Come experience the best of the North Fork!

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Remove personal items and remove leftover food and drinks
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property # 5075873vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Southold

Located in Southold, this holiday home is near the beach. The Old Field Vineyards and Mattebella Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore The Hamptons Beaches and Hallock State Park Preserve. Railroad Museum of Long Island and Greenport Carousel are also worth visiting. Spend some time exploring the area's activities, including winery tours.
Map
Southold, NY

What's nearby

  • The Old Field Vineyards - 16 min walk - 1.4 km
  • Splish Splash Water Park - 37 min drive - 41.6 km
  • The Hamptons Beaches - 42 min drive - 51.7 km
  • Shinnecock Hills Golf Course - 47 min drive - 58.0 km
  • Cooper's Beach - 56 min drive - 64.3 km

Getting around

  • Southold Station - 15 min walk
  • East Hampton, NY (HTO) - 78 min drive

Restaurants

  • ‪Dunkin' - ‬17 min walk
  • ‪North Fork Roasting Co. - ‬8 min walk
  • ‪Michelangelo's - ‬18 min walk
  • ‪Nookies - ‬6 min drive
  • ‪Southold Social - ‬7 min walk

Frequently asked questions

Does Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach?

As of 26 May, 2026, prices found for a 1-night stay for 2 adults at Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach on 27 May, 2026 start from S$656, 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.

Is Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach pet-friendly?

No, pets are not allowed at this property.

How much is parking at Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach?

On-site parking is available at the property.

What time is check-in at Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach?

Check-in begins at 3:00 PM.

What time is check-out at Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach?

Checkout is at 11:00 AM.

Where is Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach located?

Situated near the beach, this holiday home is 0.9 mi (1.5 km) from The Old Field Vineyards and within 3 miles (5 km) of Sparkling Pointe and Mattebella Vineyards. Croteaux Vineyards and Corey Creek Winery are also within 3 miles (5 km). Southold Station is 15 minutes by foot.

About the host

Hosted by Brian McCready

Host profile image

Languages:

English
Tell us how we can improve our siteShare feedback

Go further with the Vrbo app

  • Easily message your host
  • Access, share and manage your trip
  • Earn OneKeyCash on holiday rentals
Scan the QR code with your device camera and download our app
QR code to download the app