Southold Vacation Rentals

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Here is a quick list of Vacation Rentals in Southold, selected based on their rating

Name of hotel Accommodation Rating Price, $
Bright Oasis In Beautiful North Fork Wine Country

10.0 / 10

(1 Reviews)

From 1235$
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

9.6 / 10

(115 Reviews)

From 140$
Fancy Studio Private Entrance

9.3 / 10

(72 Reviews)

From 105$
Riverside Retreat-Waterfront Walkout Apartment

9.5 / 10

(82 Reviews)

From 286$
Downtown New Haven, Spacious Stay By Yale - Ao Destinations

8.8 / 10

(192 Reviews)

From 117$

Vacation rentals in Southold offer a perfect blend of relaxation and exploration, catering to various preferences and budgets. With stunning beaches, local vineyards, and scenic landscapes, this charming town on Long Island's North Fork presents a variety of rental options for travelers. From cozy cottages to luxurious waterfront homes, each property provides an opportunity to savor the tranquility of seaside living. Whether you're planning a family getaway or a romantic escape, Southold has something special for everyone.

Best Southold Vacation Rentals

Table of contents

Bright Oasis In Beautiful North Fork Wine Country Southold Cottage W/ Patio & Grill - Walk To Beach! Nf Wine Country Retreat With Dock Waterfront Home On Goose Creek Dock & Kayaks Cedar-Shake Cottage, Heated Pool And Gardens Family & Dog-Friendly Getaway! King-Bed Room With Private Bath -Free Wifi-- New London-Mystic Fancy Studio Private Entrance Riverside Retreat-Waterfront Walkout Apartment Downtown New Haven, Spacious Stay By Yale - Ao Destinations

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10
Excellent
1 Reviews

Bright Oasis In Beautiful North Fork Wine Country

📍 3795 Main Bayview Road

From 1235$

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Southold Cottage W/ Patio & Grill - Walk To Beach!

📍 Southold, Ny, 11971

From 275$

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Nf Wine Country Retreat With Dock

📍 3795 Main Bayview Rd

From 434$

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Waterfront Home On Goose Creek Dock & Kayaks

📍 900 Beachwood Ln

From 579$

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Cedar-Shake Cottage, Heated Pool And Gardens

📍 810 Waterview Dr.
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Family & Dog-Friendly Getaway!

📍 605 Highwood Road
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9.6
Excellent
115 Reviews

King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

📍 239 Williams Street

From 140$

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9.3
Excellent
72 Reviews

Fancy Studio Private Entrance

📍 28 Ormond Avenue

From 105$

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9.5
Excellent
82 Reviews

Riverside Retreat-Waterfront Walkout Apartment

📍 622 Military Highway

From 286$

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8.8
Excellent
192 Reviews

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

📍 32 Elm Street

From 117$

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9.8
Excellent
82 Reviews

The Pines Men-Only Stay

📍 488 Tarpon Walk

From 300$

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9.1
Excellent
103 Reviews

Villa Signor

📍 311 Old Pond Lane

From 236$

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9.2
Excellent
221 Reviews

The Cliffside Resort Condominiums

📍 61475 Route 48

From 513$

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9.3
Excellent
52 Reviews

Private Apt King Suite, L.I, Ny-Hamptons To Nyc

📍 1 Martin Street

From 123$

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8.7
Excellent
65 Reviews

Historic Peaceful Apartment

📍 105 Newhall Street 1

From 123$

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10
Excellent
17 Reviews

New! Updated Mystic Home W/ Sauna, Hot Tub & Deck

📍 156 Dartmouth Dr.

From 310$

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9.2
Excellent
45 Reviews

Cozy Garden Apartment Along The Shoreline

📍 14 Charles St

From 202$

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9
Excellent
88 Reviews

Hyatus Luxury Residences City Crossing

📍 9 Tower Lane

From 289$

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