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Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach
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3 bedrooms1+ bathroomSleeps 6
Popular amenities
- Private pool
- Garage parking available
- Kitchen
- Washing machine
- Air-conditioning
- Outdoor barbecue
NZ$515
NZ$515
avg per night
Explore the area
Southold, NY
- The Old Field VineyardsPlace, The Old Field Vineyards16 min walk
- The Hamptons BeachesPlace, The Hamptons Beaches34 min drive
- Cooper's BeachPlace, Cooper's Beach45 min drive
- East Hampton, NY (HTO)Airport, East Hampton, NY (HTO)53 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
The current price is NZ$515
NZ$515
avg per night
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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.
What's nearby
- The Old Field Vineyards - 16 min walk - 1.4 km
- Splish Splash Water Park - 30 min drive - 39.2 km
- The Hamptons Beaches - 34 min drive - 54.2 km
- Shinnecock Hills Golf Course - 39 min drive - 59.9 km
- Cooper's Beach - 45 min drive - 64.8 km
Getting around
- Southold Station - 15 min walk
- East Hampton, NY (HTO) - 78 min drive
Restaurants
- Dunkin' - 17 min walk
- Michelangelo's - 18 min walk
- North Fork Roasting Co. - 8 min walk
- Southold Social - 7 min walk
- Southold General - 14 min walk
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!
House Rules
Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
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
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
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 9 April 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 1 May 2026 start from NZ$515, 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.
