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351 Houses

5

Lakeside Cottage, Walk to Beach. Beautiful Sunsets

North Fork / Southold

Southold cottage

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$343

Price per night from

$343

11

Peaceful North Fork Escape - Special Spring and Summer Rates

North Fork / Southold

Southold house

3 5 14 nights min

  • 3 bedrooms
  • sleeps 5
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$287

Price per night from

$287

34

Beach Cottage, Bring The Dog, Founders Landing Beach, Southold, North Fork, NY

North Fork / Southold

Southold house

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$400

Price per night from

$400

(2) Excellent 

17

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 mi
  • Child Friendly

Price per night from

$430

Price per night from

$430

(1) Excellent 

19

Beautiful Classic North Fork Home, wrap around porch, pool, walk to beach

North Fork / Southold

Southold house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0.8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$344

Price per night from

$344

15

Southold Summer Home for rent

North Fork / Southold

Southold house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$532

Price per night from

$532

18

North Fork Beach Bungalow

North Fork / Southold

Southold house

5 10 14 nights min

  • 5 bedrooms
  • sleeps 10
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$573

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$573

24

NEW! Waterfront Southhold Home w/ Sauna & Dock!

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$401

Responds fast!
avg. 28 minutes

Price per night from

$401

19

Southold Contemporary Summer Home Steps from Beach and Vineyard

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$430

Price per night from

$430

(2) Excellent 

16

Beach House In Wine Country; walk to beach, large sun room, outdoor dining

North Fork / Southold

Southold cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$373

Price per night from

$373

21

Private Waterfront W Beach, New Renovation

North Fork / Southold

Southold house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 mi
  • Ask about children

Price per night from

$602

Price per night from

$602

24

Beach Front, spacious 5 Bedrooms, North Fork, Long Island

North Fork / Southold

Southold house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$602

Price per night from

$602

(3) Excellent 

32

Shorecrest Beach House, 4 bedroom private beach front, new renovation

North Fork / Southold

Southold house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$572

Price per night from

$572

Great rentals within 20 miles that match your search

Distance approx 15.25 km from Southold

9

Private 2 Bdrm Cottage, Walk 2 Beach & Riverfront!

Connecticut / Westbrook

Westbrook cottage

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$400

Price per night from

$400

Distance approx 6.21 km from Southold

(5) Excellent 

23

Beautiful French Country Cottage

North Fork / East Marion

East Marion cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$456

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$456

Distance approx 9.33 km from Southold

24

New! 3BR Sag Harbor Cottage w/ Modern Charm!

Hamptons / Sag Harbor

Sag Harbor cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$508

Responds fast!
avg. 9 minutes

Price per night from

$508

Distance approx 14.03 km from Southold

41

New Luxury Waterfront Home

Connecticut / Clinton

Clinton house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$569

Responds fast!
avg. 1 hour 44 minutes

Price per night from

$569

Distance approx 9.41 km from Southold

13

North Fork Loft - Perfect for Wine & Food Weekends

North Fork / Mattituck

Mattituck apartment

5 14 2 nights min

  • 5 bedrooms
  • sleeps 14
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 mi
  • Ask about children

Price per night from

$1,022

Price per night from

$1,022

Distance approx 12.07 km from Southold

7

Private Suite in Contemporary Home

Hamptons / East Hampton

East Hampton house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Ask about pets

Price per night from

$455

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$455

Distance approx 13.65 km from Southold

18

Waterview renovated 5 bedroom house with pool

Hamptons / East Hampton

East Hampton house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,145

Price per night from

$1,145

Distance approx 17.59 km from Southold

15

Pristine Southampton Architect Home, Pool & Tennis

Hamptons / East Quogue

East Quogue house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

Price per night from

$1,088

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$1,088

Distance approx 13.66 km from Southold

24

Serene East Hampton Apt. w/ Private Yard & Pool!

Hamptons / East Hampton

East Hampton apartment

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$98

Responds fast!
avg. 9 minutes

Price per night from

$98

Distance approx 14.42 km from Southold

(2) Excellent 

12

Grace Cottage

Hamptons / East Hampton

East Hampton house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly
“Welcome Respite” We've been lucky enough to stay at Grace Cottage a number of times and have always felt refreshed and grateful after our time there. Great sun rises, great sunsets only a short trip away. It's been relaxation at its best!
…see more

Price per night from

$574

Price per night from

$574

Distance approx 8.19 km from Southold

24

Idyllic hideaway--private swimming pond, waterfall, tennis, yacht-like interior

Hamptons / Southampton

Southampton house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$342

Price per night from

$342

Distance approx 12.02 km from Southold

9

Seahaven Resort Motel Unit 8

Hamptons / Southampton

Southampton hotel apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$170

Price per night from

$170

Distance approx 12.21 km from Southold

7

SOUTHAMPTON VACATION HOME

Hamptons / Southampton

Southampton house

5 16 7 nights min

  • 5 bedrooms
  • sleeps 16
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

Price per night from

$1,467

Price per night from

$1,467

Distance approx 10.9 km from Southold

24

Live in Luxury in This English Manor Home.

Hamptons / East Hampton

East Hampton house

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$3,712

Price per night from

$3,712

Distance approx 9.66 km from Southold

24

Amazing Hampton's Styled Getaway

Hamptons / Water Mill

Water Mill house

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child Friendly

Price per night from

$771

Price per night from

$771

Distance approx 12.17 km from Southold

17

Southampton Village Charmer with New Heated Pool

Hamptons / Southampton

Southampton house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,711

Price per night from

$1,711

Distance approx 8.74 km from Southold

7

Village traditional on a quiet cul de sac

Hamptons / Sag Harbor

Sag Harbor house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,272

Price per night from

$1,272

Distance approx 18.4 km from Southold

(2) Excellent 

13

Newly Renovated Water Front Home!!

Hamptons / Amagansett

Amagansett house

3 8 6 nights min

  • 3 bedrooms
  • sleeps 8
  • 6 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$1,145

Price per night from

$1,145

Distance approx 14.45 km from Southold

(1)  

23

Hampton Accommodations 3 / FREE BIKE RENTALS

Hamptons / East Hampton

East Hampton b and b

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi

Price per night from

$285

Responds fast!
avg. 2 hours 0 minutes

Price per night from

$285

Distance approx 12.04 km from Southold

19

in town of east hampton, bike to beach

Hamptons / Wainscott

Wainscott house

4 10 30 nights min

  • 4 bedrooms
  • sleeps 10
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,085

Price per night from

$1,085

Distance approx 12.02 km from Southold

10

Seahaven Resort Motel Unit 7

Hamptons / Southampton

Southampton hotel apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$205

Price per night from

$205

Distance approx 13.98 km from Southold

15

Modern Interior. Private, Spacious Grounds.

Hamptons / Springs

Springs house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$1,511

Price per night from

$1,511

Distance approx 6.43 km from Southold

41

LOVELY LARGE RESTORED FARMHOUSE IN BEAUTIFUL EAST MARION

North Fork / East Marion

East Marion house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$742

Responds fast!
avg. 2 hours 1 minutes

Price per night from

$742

Distance approx 13.01 km from Southold

(10) Excellent 

37

North Fork 5 bed room home with forever farm view

Riverhead / Aquebogue

Aquebogue house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$456

Price per night from

$456

Distance approx 6.66 km from Southold

15

Modern 3 Bedroom 2 Bath Waterfront House with Private Beach!

North Fork / East Marion

East Marion house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$537

Price per night from

$537