Resorts Space Southold
Southold
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Southold

Oct 21 - Oct 22 ·
2 guests

Southold Vacation Rentals

Southold
2 guests

Adults:

2

Children:

0

Child’s age:

Over 10 stays assessed to highlight the standout picks

Navigation

1. Bright Oasis In Beautiful North Fork Wine Country

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

3. Nf Wine Country Retreat With Dock

4. Waterfront Home On Goose Creek Dock & Kayaks

Cheap Southold Vacation Rentals

5. Cedar-Shake Cottage, Heated Pool And Gardens

6. Family & Dog-Friendly Getaway!

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

Pet Friendly Vacation Rentals Southold

8. Fancy Studio Private Entrance

9. Riverside Retreat-Waterfront Walkout Apartment

10. Downtown New Haven, Spacious Stay By Yale - Ao Destinations

Best Southold Vacation Rentals

Bright Oasis In Beautiful North Fork Wine Country Bright Oasis In Beautiful North Fork Wine Country

Bright Oasis In Beautiful North Fork Wine Country

3795 Main Bayview Road
2.3 km (1.4 mi) from city center
153
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Sun terrace
10
1 reviews
~ US$1235 / night

Bright Oasis In Beautiful North Fork Wine Country

2.3 km (1.4 mi) from city center
153
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Sun terrace

Bright Oasis In Beautiful North Fork Wine Country

10
1 reviews
From US$ 1235 / night
  • Beach access
Southold Cottage W/ Patio & Grill - Walk To Beach! Southold Cottage W/ Patio & Grill - Walk To Beach!

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

Southold, Ny, 11971
3.0 km (1.9 mi) from city center
41
  • Cookware/ Kitchen utensils
  • Free parking
  • Terrace
  • Patio
~ US$275 / night

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

3.0 km (1.9 mi) from city center
41
  • Cookware/ Kitchen utensils
  • Free parking
  • Terrace
  • Patio

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

From US$ 275 / night
Nf Wine Country Retreat With Dock Nf Wine Country Retreat With Dock

Nf Wine Country Retreat With Dock

3795 Main Bayview Rd
2.3 km (1.4 mi) from city center
158
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Garden area
~ US$434 / night

Nf Wine Country Retreat With Dock

2.3 km (1.4 mi) from city center
158
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Garden area

Nf Wine Country Retreat With Dock

From US$ 434 / night

Cheap Southold Vacation Rentals

  • Top location
  • Beach access
Waterfront Home On Goose Creek Dock & Kayaks Waterfront Home On Goose Creek Dock & Kayaks

Waterfront Home On Goose Creek Dock & Kayaks

900 Beachwood Ln
1.6 km (1.0 mi) from city center
167
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio
~ US$579 / night

Waterfront Home On Goose Creek Dock & Kayaks

1.6 km (1.0 mi) from city center
167
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Waterfront Home On Goose Creek Dock & Kayaks

From US$ 579 / night
  • Great deal
  • Beach access
Cedar-Shake Cottage, Heated Pool And Gardens Cedar-Shake Cottage, Heated Pool And Gardens

Cedar-Shake Cottage, Heated Pool And Gardens

810 Waterview Dr.
2.4 km (1.5 mi) from city center
102
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Outdoor swimming pool

Cedar-Shake Cottage, Heated Pool And Gardens

2.4 km (1.5 mi) from city center
102
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Outdoor swimming pool

Cedar-Shake Cottage, Heated Pool And Gardens

Family & Dog-Friendly Getaway! Family & Dog-Friendly Getaway!

Family & Dog-Friendly Getaway!

605 Highwood Road
2.7 km (1.7 mi) from city center
195
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

Family & Dog-Friendly Getaway!

2.7 km (1.7 mi) from city center
195
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

Family & Dog-Friendly Getaway!

Vacation rentals near Southold

Pet Friendly Vacation Rentals Southold

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

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

239 Williams Street
42.5 km (26.4 mi) from Southold
17
  • Shared kitchen
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tea and coffee facilities
  • Heating
9.6
115 reviews
~ US$140 / night

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

42.5 km (26.4 mi) from Southold
17
  • Shared kitchen
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tea and coffee facilities
  • Heating

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

9.6
115 reviews
From US$ 140 / night
Fancy Studio Private Entrance Fancy Studio Private Entrance

Fancy Studio Private Entrance

28 Ormond Avenue
55.4 km (34.4 mi) from Southold
215
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities
  • Patio
9.3
72 reviews
~ US$105 / night

Fancy Studio Private Entrance

55.4 km (34.4 mi) from Southold
215
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Fancy Studio Private Entrance

9.3
72 reviews
From US$ 105 / night
Riverside Retreat-Waterfront Walkout Apartment Riverside Retreat-Waterfront Walkout Apartment

Riverside Retreat-Waterfront Walkout Apartment

622 Military Highway
45.4 km (28.2 mi) from Southold
84
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Terrace
9.5
82 reviews
~ US$286 / night

Riverside Retreat-Waterfront Walkout Apartment

45.4 km (28.2 mi) from Southold
84
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Terrace

Riverside Retreat-Waterfront Walkout Apartment

9.5
82 reviews
From US$ 286 / night

Southold Vacation Rentals Oceanfront

Downtown New Haven, Spacious Stay By Yale - Ao Destinations Downtown New Haven, Spacious Stay By Yale - Ao Destinations

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

32 Elm Street
49.5 km (30.7 mi) from Southold
  • Car park
    Charges may apply
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating
8.8
192 reviews
~ US$117 / night

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

49.5 km (30.7 mi) from Southold
  • Car park
    Charges may apply
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

8.8
192 reviews
From US$ 117 / night
  • Beach access
The Pines Men-Only Stay The Pines Men-Only Stay

The Pines Men-Only Stay

488 Tarpon Walk
69.3 km (43.1 mi) from Southold
  • VIP check-in/ -out
  • Air conditioning
  • Fitness centre
  • Saltwater pool
  • Heated swimming pool
  • Outdoor swimming pool
9.8
82 reviews
~ US$300 / night

The Pines Men-Only Stay

69.3 km (43.1 mi) from Southold
  • VIP check-in/ -out
  • Air conditioning
  • Fitness centre
  • Saltwater pool
  • Heated swimming pool
  • Outdoor swimming pool

The Pines Men-Only Stay

9.8
82 reviews
From US$ 300 / night
Villa Signor Villa Signor

Villa Signor

311 Old Pond Lane
55.8 km (34.7 mi) from Southold
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Steam room
  • Outdoor swimming pool
9.1
103 reviews
~ US$236 / night

Villa Signor

55.8 km (34.7 mi) from Southold
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Steam room
  • Outdoor swimming pool

Villa Signor

9.1
103 reviews
From US$ 236 / night

Southold Vacation Rentals with Private Pool

  • Guest favorite
  • Private beach
The Cliffside Resort Condominiums The Cliffside Resort Condominiums

The Cliffside Resort Condominiums

61475 Route 48
5.0 km (3.1 mi) from Southold
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Outdoor swimming pool
9.2
221 reviews
~ US$513 / night

The Cliffside Resort Condominiums

5.0 km (3.1 mi) from Southold
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Outdoor swimming pool

The Cliffside Resort Condominiums

9.2
221 reviews
From US$ 513 / night
Private Apt King Suite, L.I, Ny-Hamptons To Nyc Private Apt King Suite, L.I, Ny-Hamptons To Nyc

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

1 Martin Street
51.4 km (31.9 mi) from Southold
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Luggage storage
  • Tea and coffee facilities
9.3
52 reviews
~ US$123 / night

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

51.4 km (31.9 mi) from Southold
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Luggage storage
  • Tea and coffee facilities

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

9.3
52 reviews
From US$ 123 / night
Historic Peaceful Apartment Historic Peaceful Apartment

Historic Peaceful Apartment

105 Newhall Street 1
51.2 km (31.8 mi) from Southold
11
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Skiing
  • Garden area
8.7
65 reviews
~ US$123 / night

Historic Peaceful Apartment

51.2 km (31.8 mi) from Southold
11
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Skiing
  • Garden area

Historic Peaceful Apartment

8.7
65 reviews
From US$ 123 / night
New! Updated Mystic Home W/ Sauna, Hot Tub & Deck New! Updated Mystic Home W/ Sauna, Hot Tub & Deck

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

156 Dartmouth Dr.
50.2 km (31.2 mi) from Southold
144
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Sauna
  • Terrace
10
17 reviews
~ US$310 / night

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

50.2 km (31.2 mi) from Southold
144
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Sauna
  • Terrace

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

10
17 reviews
From US$ 310 / night
  • Private beach
Cozy Garden Apartment Along The Shoreline Cozy Garden Apartment Along The Shoreline

Cozy Garden Apartment Along The Shoreline

14 Charles St
30.4 km (18.9 mi) from Southold
400
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun loungers
9.2
45 reviews
~ US$202 / night

Cozy Garden Apartment Along The Shoreline

30.4 km (18.9 mi) from Southold
400
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun loungers

Cozy Garden Apartment Along The Shoreline

9.2
45 reviews
From US$ 202 / night
Hyatus Luxury Residences City Crossing Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

9 Tower Lane
49.6 km (30.8 mi) from Southold
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Fitness centre
  • Rooftop pool
9
88 reviews
~ US$289 / night

Hyatus Luxury Residences City Crossing

49.6 km (30.8 mi) from Southold
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Fitness centre
  • Rooftop pool

Hyatus Luxury Residences City Crossing

9
88 reviews
From US$ 289 / night
Beautiful Studio Apartment In Historic House Beautiful Studio Apartment In Historic House

Beautiful Studio Apartment In Historic House

105 Newhall Street
51.2 km (31.8 mi) from Southold
9
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area
8.5
74 reviews
~ US$175 / night

Beautiful Studio Apartment In Historic House

51.2 km (31.8 mi) from Southold
9
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area

Beautiful Studio Apartment In Historic House

8.5
74 reviews
From US$ 175 / night

Are you in a hurry?

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$

Location