Accommodations in Southold, NY: Compare 10+ Sites & Save

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388 Best Accommodations 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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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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Vine & Sand-Southold NY's Newest B&B
Vine & Sand-Southold NY's Newest B&B
Bed & Breakfast
Southold, NY, USA
1.7k from Southold center

B&bs, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Jacuzzis, Places to stay

4 Bedrooms8 Guests
9.0

Fabulous

4 reviews

$689
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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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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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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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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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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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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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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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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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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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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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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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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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
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Charming Northfork home.
Charming Northfork home.
House
Southold, NY, 11971, United States
1.3k from Southold center

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

3 Bedrooms6 Guests
10.0

Exceptional

16 reviews

$538
Average price / night
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NorthFork Serenity, next to beach and wineries
NorthFork Serenity, next to beach and wineries
House
Southold, NY, 11971, United States
1.3k from Southold center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$642
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 Accommodations in Southold.

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Southold Accommodations on the Map

Frequently Asked Questions

You can explore 388 verified accommodations in Southold, including hotels, vacation rentals, resorts, and boutique stays. This variety makes it easier to choose the option that best fits your travel style and budget.

Accommodation prices in Southold vary based on property type, location, and travel dates. Rates typically start from around $164 per night, with higher prices for premium properties and peak travel periods.

Hotels are ideal for convenience and short stays, while vacation rentals offer more space and privacy. Resorts are suitable for all-inclusive experiences, and boutique properties provide a more unique and personalized stay in Southold.

Yes, Southold offers many family-friendly options, including large vacation rentals and hotels with suites or connecting rooms. Currently, 42 listings in Southold are well-suited for families and group travel.

Booking 30 to 60 days in advance is generally recommended for the best availability and pricing. For peak travel seasons or major events in Southold, booking several months ahead can help secure your preferred property.

Accommodations in Southold commonly include amenities such as View, Fireplace/Heating, and Balcony/Terrace. Availability may vary depending on the type of property you choose.

Yes, some accommodations in Southold focus on sustainable practices such as energy efficiency and reduced environmental impact. You can filter listings to find options that align with your preferences in Southold.