Short-Term Rentals in Southold, NY: Compare 10+ Sites & Save

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417 Best Short-Term Rentals in Southold (Starting from $164)

Classic Southold Country Charmer
Classic Southold Country Charmer
House
Southold, NY, USA
0.7k from Southold center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$233
Average price / night
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Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries\n\n\n\n
Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries\n\n\n\n
House
Southold, NY, 11971, United States
0.3k from Southold center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$510
Average price / night
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Private Waterfront Home: Dock, Kayaks
Private Waterfront Home: Dock, Kayaks
House
Southold, NY, USA
1.2k from Southold center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$801
Average price / night
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Farmhouse Retreat
Farmhouse Retreat
House
Southold, NY, 11971, United States
0.4k from Southold center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$780
Average price / night
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Private Waterfront home Dock Kayak walk to Southold, near Greenp
Private Waterfront home Dock Kayak walk to Southold, near Greenp
House
Southold, New York, USA
1.2k from Southold center

Parking, Child Friendly

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$389
Average price / night
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Charming Cottage
Charming Cottage
Cottage
Southold, NY, 11971, United States
0.5k from Southold center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

34 reviews

$474
Average price / night
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Bright Oasis in Beautiful North Fork Wine Country
Bright Oasis in Beautiful North Fork Wine Country
House
Southold, NY, USA
1.8k from Southold center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$391
Average price / night
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Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
House
Southold, NY, 11971, United States
0.6k from Southold center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms9 Guests
9.8

Exceptional

6 reviews

$935
Average price / night
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NF Wine Country Retreat with Dock
NF Wine Country Retreat with Dock
House
Southold, NY, USA
1.8k from Southold center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$499
Average price / night
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House of Classic Arts and Crafts North Fork
House of Classic Arts and Crafts North Fork
House
Southold, NY, 11971, United States
0.6k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$455
Average price / night
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Steve's Place: Heated Pool, 3BR Southold Home, Beach
Steve's Place: Heated Pool, 3BR Southold Home, Beach
House
Southold, NY, USA
1.9k from Southold center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$304
Average price / night
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Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
House
Southold, NY, 11971, United States
0.6k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.4

Superb

14 reviews

$447
Average price / night
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Southold Cottage with Patio and Grill - Walk to Beach!
Southold Cottage with Patio and Grill - Walk to Beach!
House
Southold, New York, USA
2.5k from Southold center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms3 Guests
New to Booking
$164
Average price / night
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Cozy studio with WiFi and AC in welcoming Southold
Cozy studio with WiFi and AC in welcoming Southold
Apartment
Southold, NY, 11971, United States
0.7k from Southold center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking, Patio

1 Bedroom3 Guests
9.2

Superb

7 reviews

$284
Average price / night
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Minnehaha Marvel
Minnehaha Marvel
House
Southold, NY, USA
2.5k from Southold center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom4 Guests
New to Booking
$296
Average price / night
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Country BEACH home!
Country BEACH home!
House
Southold, NY, 11971, United States
0.9k from Southold center

AC, Dryer, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$826
Average price / night
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Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
3.3k from Southold center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

3 Bedrooms6 Guests
New to Booking
$811
Average price / night
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2 Bedroom Apartment in Historic Home with private yard
2 Bedroom Apartment in Historic Home with private yard
Apartment
Southold, NY, 11971, United States
0.9k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.6

Exceptional

37 reviews

$434
Average price / night
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Happiness Comes in Waves
Happiness Comes in Waves
House
Southold, New York, USA
3.7k from Southold center

Kitchen, Internet, Air Conditioner, Parking, Balcony/Terrace, Pet Friendly, Child Friendly

4 Bedrooms10 Guests
New to Booking
$438
Average price / night
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Cute Cottage Apartment Near town, beaches and vineyards
Cute Cottage Apartment Near town, beaches and vineyards
Cottage
Southold, NY, 11971, United States
0.9k from Southold center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.6

Exceptional

26 reviews

$457
Average price / night
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Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
House
Southold, NY, 11971, United States
0.9k from Southold center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$398
Average price / night
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Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach
Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach
House
Southold, NY, 11971, United States
1.0k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$354
Average price / night
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Traditional Southold Home, Private Pool, Perfect for Families
Traditional Southold Home, Private Pool, Perfect for Families
House
Southold, NY, 11971, United States
1.0k from Southold center

5 Bedrooms8 Guests
New to Booking
$789
Average price / night
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Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
House
Southold, NY, 11971, United States
1.1k from Southold center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms2 Guests
7.0

Good

2 reviews

$280
Average price / night
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Stylish beach getaway: pool in prime location
Stylish beach getaway: pool in prime location
House
Southold, NY, 11971, United States
1.2k from Southold center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$979
Average price / night
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Southold 3BR Waterfront Home | Dock, Kayaks, Creek Views
Southold 3BR Waterfront Home | Dock, Kayaks, Creek Views
House
Southold, NY, 11971, United States
1.2k from Southold center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.4

Superb

21 reviews

$639
Average price / night
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Enjoy Driftwood Landing - A Quiet Southold Escape
Enjoy Driftwood Landing - A Quiet Southold Escape
House
Southold, NY, 11971, United States
1.3k from Southold center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$871
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Southold.

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Southold Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 417 verified short-term rentals in Southold, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Southold vary depending on location, property size, and travel dates. Rates typically start from around $164 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Southold include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Southold, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Southold often include amenities such as View, Fireplace/Heating, and Balcony/Terrace, providing a comfortable and convenient stay.

Short-term rentals in Southold are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.