Southold Vacation Rentals

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Best Southold Vacation Rentals

Southold vacation rentals provide a comfortable and flexible choice for travelers, with options ranging from charming cottages to spacious family homes. These rentals are conveniently located near vineyards and local attractions, giving guests ample opportunities to explore the area.

8.7

Good

(153 Reviews)

+ 20 photos

Southold Beach Motel

53250 North Road
Free Wi-Fi
Free parking
Picnic area/ Tables
Flat-screen TV
Beach access
Air conditioning
No smoking on site
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Southold Beach Motel offers comfortable family accommodations with modern amenities, including private bathrooms and free WiFi. Located just a 6-minute walk from Hashamomuck Beach, guests can easily access local attractions like Lavender By the Bay Farm, situated 4 miles away. The motel also features outdoor spaces, including a sun terrace and garden, allowing guests to relax outdoors.

Price comparison

Average Price 250 US$

9.6

Good

(16 Reviews)

+ 24 photos

A Walk In The Woods Bed And Breakfast

9680 North Bayview Road
Free Wi-Fi
Free parking
Flat-screen TV
Adults only
Hiking
Air conditioning
No smoking on site
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A Walk In The Woods Bed And Breakfast offers adults-only accommodations in a serene woodland setting. Guests enjoy breakfast with warm dishes and fruits, and facilities include a terrace with free WiFi. Located only 1 mile from Cedar Beach County Park, travelers can engage with the local environment, with attractions like Catapano Dairy Farm nearby.

Price comparison

Average Price 410 US$

9.3

Good

(12 Reviews)

+ 54 photos

Historic White Blossom House

695 Pine Neck Road
Free Wi-Fi in rooms
Free parking
Outdoor dining area
Picnic area/ Tables
Laundry
Flat-screen TV
Dryer
Cookware/ Kitchen utensils
VIP check-in/ -out
Hiking
Cycling
Canoeing
Fishing
Wind surfing
Horseback riding
Golf course
Tennis court
Sun loungers
Beach umbrellas
Video games
Cribs
Board games
Pets allowed
Air conditioning
No smoking on site
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Historic White Blossom House provides a 2-star experience situated within a historically significant building. With comfortable amenities, including bicycles for rent, this location is ideal for exploring Southold's rich history. Guests are within 2 miles of Old Field Vineyards and can indulge in outdoor activities like hiking and cycling.

Price comparison

Average Price 844 US$

+ 21 photos

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

Southold, Ny, 11971
Wi-Fi
Free parking
Cookware/ Kitchen utensils
Outdoor dining area
Beach access
Board games
No pets allowed
No smoking on site
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Southold Cottage w/ Patio & Grill offers a spacious holiday home with modern amenities including a fireplace and kitchen. Located within close proximity to attractions like Coffee Pot Cellars and Horton Point Light, this cottage is perfect for families and groups looking to enjoy the nearby beaches and restaurants.

Price comparison

Average Price 275 US$

9.6

Good

(38 Reviews)

+ 47 photos

The Shoals Suites & Slips

61600 Main Road
Free Wi-Fi in rooms
Free parking
Baggage storage
24-hour security
Bar/ Lounge area
Picnic area/ Tables
Business center
Cribs
No pets allowed
Air conditioning
No smoking on site
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The Shoals Suites & Slips offers a blend of comfort and style with air-conditioned rooms featuring private bathrooms and balconies. Guests can unwind at the sun terrace and enjoy the garden space. Located just under 0.5 miles from Old Field Vineyards, this property is rated highly for its accessibility to local attractions and dining.

Price comparison

Average Price 199 US$

9.4

Good

(7 Reviews)

+ 63 photos

Vine & Sand--Southold Ny'S Newest B&B

47100 New York 25
Wi-Fi
Free parking
Baggage storage
Outdoor dining area
Seasonal outdoor pool
Heated swimming pool
Jacuzzi
Adults only
VIP check-in/ -out
Cycling
Sun loungers
Beach umbrellas
No pets allowed
Air conditioning
No smoking on site
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Vine & Sand is a delightful bed and breakfast located in a historic building in Southold. This property features a seasonal outdoor swimming pool and sun terrace, creating a relaxing atmosphere for guests. Located near Old Field Vineyards, it provides easy access to local attractions and delicious buffet breakfasts and is perfect for a peaceful getaway.

Price comparison

Average Price 765 US$

10.0

Good

(1 Reviews)

+ 33 photos

Bright Oasis In Beautiful North Fork Wine Country

3795 Main Bayview Road
Wi-Fi
Free parking
Dryer
Cookware/ Kitchen utensils
Air conditioning
Flat-screen TV
Canoeing
Outdoor dining area
Sun loungers
Playpen
Cribs
Board games
Pets allowed
No smoking on site
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Bright Oasis in Beautiful North Fork Wine Country features a welcoming holiday home, suitable for families or group gatherings with four bedrooms. The spacious outdoor areas provide guests with places to relax while enjoying the picturesque surroundings near local wineries, with Old Field Vineyards just 3 miles away.

Price comparison

Average Price 1235 US$

+ 29 photos

Cedar-Shake Cottage, Heated Pool And Gardens

810 Waterview Dr.
Free Wi-Fi in public areas
Free parking
Dryer
Cookware/ Kitchen utensils
Air conditioning
Flat-screen TV
Beach access
Sun loungers
Outdoor swimming pool
Pets allowed
No smoking on site
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Cedar-Shake Cottage offers a tranquil retreat with comfortable living spaces, three bedrooms, and a private pool. Guests can also enjoy a beautifully maintained garden and modern amenities, including a kitchen suitable for preparing home-cooked meals.

Price comparison

+ 30 photos

Waterfront Home On Goose Creek Dock & Kayaks

900 Beachwood Ln
Free Wi-Fi in public areas
Free parking
Dryer
Cookware/ Kitchen utensils
Air conditioning
Flat-screen TV
Beach access
Pets allowed
No smoking on site
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Waterfront Home on Goose Creek Dock & Kayaks offers a beautiful getaway with three bedrooms and ample indoor/outdoor space. Guests are provided with a fully equipped kitchen, making it easy to prepare meals after a day of exploring nearby attractions like Jacqueline Penney Art Gallery and local wineries, with Old Field Vineyards a short drive away.

Price comparison

Average Price 579 US$

+ 24 photos

Nf Wine Country Retreat With Dock

3795 Main Bayview Rd
Wi-Fi
Free parking
Air conditioning
Flat-screen TV
Beach umbrellas
Cribs
Pets allowed
No smoking on site
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NF Wine Country Retreat With Dock provides guests with a spacious escape in Southold, featuring a garden and modern amenities. This holiday home is perfect for relaxation after visiting local wineries, art galleries, and nature parks. Located just a short distance from Old Field Vineyards, travelers looking to explore the rich wine country will find this retreat ideal.

Price comparison

Average Price 434 US$

Located on the picturesque North Fork of Long Island, Southold is rich in history and natural beauty. Founded in 1640, the town offers scenic vineyards like Old Field Vineyards and stunning coastal views, while its beaches provide relaxation and outdoor activities. With 10 vacation rentals available, Southold is an excellent home base for travelers seeking a blend of cultural experiences and leisure. The Shoals Suites & Slips offers unique proximity to local wineries and beaches, while A Walk in the Woods Bed and Breakfast provides a cozy and intimate atmosphere.

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